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Organic Chemistry

UNIT

Section A : Straight Objective Type


1. Answer (3)

COOH OH
Due to ortho effect, 2. 3. 4. Answer (3) On the abstraction of H(d), allyl free radical as well as tertiary free radical is formed. Answer (3) Electron withdrawing group increases rate for SN reactions. Answer (2) is most acidic.

Aromatic + resonance stabilised

CH2
resonance stabilised

CH2 = CH C H2

resonance stabilised

CH2 = C H least stable due to presence of positive charge on sp hybridised carbon.


5. 6. 7. Answer (4) Number of stereoisomers = 2n (n = number of asymmetric carbon atoms + number of double bonds) Answer (1) Meso tartaric acid is optically inactive due to presence of plane of symmetry. Answer (1)

CH3
The Fisher projection of the compound is HO

CH3 H and it has R & R configuration on both

H
asymmetric C-atom. 8. Answer (1)

OH

p orbitals of carbon being restricted rotation H HCCCCH H H H H H

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Organic Chemistry

9.

Answer (3)

CH3 C HOH C HOH COOH


No. of chiral carbon atoms = 2 No. of optical isomers = 2n = 22 = 4 10. Answer (2)
6 4 3 2 7 1
3

Cl

Positive charge due to delocalisation of electrons is present 1, 3, 5 and 7 carbon. 11. Answer (1) Bridge head carbocation is not possible. 12. Answer (2)

OH H
+

ring expansion

13. Answer (1) N2 is good leaving group, resulting in the formation of carbene. 14. Answer (4) OCH3 group is +R group which would decrease the magnitude of + charge. 15. Answer (1)

H
OH

Conjugate base is resonance stabilised and is aromatic. 16. Answer (2) Compounds containing N and S respond to this test. 17. Answer (2) HNO 3 decomposes Na2 S and NaCN present in Lassaigne extract becuase otherwise they will give precipitation with AgNO3.
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18. Answer (3)

Stabilised due to aromatic nature and is resonance stabilised.

19. Answer (3)

CH = CH O H

CH2 CHO

OH

O NH

OH NH2

20. Answer (4) Pyrolle is least basic as the lone pair is contributing to aromaticity of the molecule. In pyridine
N

N is sp2 hybridised.

is most basic, therefore 6 member ring is least strained.

N H
21. Answer (2)
CH 3 O CH 2 stabilised due to lone pair of O.

22. Answer (2)


B C cyclic delocalisation of 6 electrons.

23. Answer (2) Br is a good leaving group and carbonyl site has electron deficient carbon. 24. Answer (1) Alkenes undergo electrophilic addition reaction. Carbonyl undergo electrophilic addition reaction. 25. Answer (4)

sp2 hybridised carbon cannot be readily attacked by nucleophile from back side and attack at bridgehead carbon is not feasible.
26. Answer (2)
2 has (4n + 2) electrons and planar ring.
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27. Answer (4)

CH2OH H H HO CH2OH
28. Answer (1)

S S H H HO

CH2OH

S OH S

OH OH H

OH H CH2OH

Br C l , so Cl will add at most stable carbocationic site.

29. Answer (2) Ketal formation. 30. Answer (4)


1 , 2 and 3 has plane of symmetry.

31. Answer (3) In ortho substituted amines, nitrogen moves out of the plane. 32. Answer (1)
1 and 2 are resonance stabilised but 2 is less stabilised since it has electron withdrawing nitro group.

33. Answer (2) Aliphatic amine is more basic and lone pair e of pyrolle participate in resonance. 34. Answer (4) Percentage of 1 chloro-3-methyl butane = 35. Answer (1)
1 3 100 3 = 100 = 13.88% 1 3 + 6 1 + 1 5 + 2 3.8 9 + 5 + 7.6

Cl

Cl C CH CH3 < Cl C CH2 CH2 (more stable carbocation) Cl


36. Answer (4) H3O+ gives A i.e. Markownikovs addition, through carbocation formation. B formed by hydroboration oxidation that gives anti-Markownikovs product. 37. Answer (2)

Cl

Cl

H+

Hydride transfer H

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38. Answer (2) OH group of molecule will behave as a basic site in presence of HCl. 39. Answer (2) Gauche form is more stable due to presence of intramolecular hydrogen bonding. 40. Answer (2) Lemeiux reagent will add OH at each site after cleavage of every bond. 41. Answer (3)

Br Br
42. Answer (2)
2NaNH2 NaNH2

Na

C2H5Br

C2H5

CH3 CCCC CH3 H H

H C CH3

CH3 H2 CH = CH C CH3 H CH CH CH3

(optically inactive)

Triple bond is more sensitive for addition H2 than double bond. 43. Answer (3)
H2O Hg CaO + C CaC2 C2H2 CH3 CHO H2SO 4
2+

44. Answer (2)


H C=C H 3C H CH3
CH2N2 : CH2

H CC H 3C

CH3 H

45. Answer (2) Na give electron resulting the formation of free radical. 46. Answer (2)

COONa
Sodalime COCl Anhyd. AlCl3

CO

A
47. Answer (1)

B (ketone)

Cl

AlCl3

48. Answer (2)

OH CH3CH2 C CH
H2O Hg , H
2+ +

O CH3 CH2 C CH3

CH3CH2 C = CH2

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49. Answer (2) KMnO4 (H+) cold gives syn hydroxylation. 50. Answer (3)

Cl
Cl Cl
, ,

Cl

Cl
51. Answer (4) Peracids give epoxy formation. 52. Answer (1) Peroxy acid form epoxy alkane. 53. Answer (2)
CH3 C CNa 54. Answer (2)
C2H5Br

Cl

Cl Cl

CH3 C C C H2 CH3

O3
55. Answer (2)

O CHO

Thiophene undergoes electrophilic substitution at 2nd position. 56. Answer (2)

(CH3)2 C = = CH2

(CH3)2 C CH3

(CH3)2 C = = CH2

(CH3)2 C CH3 CH2 C (CH3)2


H
+

(CH3)3 C CH3 CH = =C

CH3 CH3

57. Answer (2)

CH2 = CH CH = CH2

H2 1, 4 addition

CH3 CH = CH CH3 A

O3/H2O 1, 4 addition

2CH3COOH B

(Zinc is not present hence CH3CHO first formed oxidised to CH3COOH) 58. Answer (3)
Br CH3 CH CH = = CH2
H
+

CH3 CH CH CH3 CH3

1-2 H shift

CH3 C CH2 CH3 CH3

Br

CH3 C CH2 CH3 CH3 (3 more stable than 2)

59. Answer (3) Triple bond is more reactive than double bond for hydrogenation. 60. Answer (1) Chlorine free radical is prepared in presence of ultraviolet light.
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61. Answer (3) Carbocation formation and ring expansion takes place. 62. Answer (1) Due to high electronegativity of carbon. 63. Answer (3)

O O CH3 C C CH2CH3
O3

CH3 C C C2H5
Li AlH4

OH OH CH3 C C C2H5 H
64. Answer (4) Free radical substitution takes place in presence of sunlight. 65. Answer (3)

Chiral centre = 2 Stereoisomer = 4

COCl Anhyd. AlCl3 NO2


66. Answer (1)

CO Given product. NO2

1 Kolbes electrolytic reaction.

67. Answer (4)


NaNH2 3 CH3 C C H CH3 C C Na CH3 C C CH3 CH

68. Answer (3) Williamsons synthesis. 69. Answer (4) Benzyl fluoride form soluble AgF and alkyl bromide give yellow ppt of AgBr. Vinyl chloride does not react. 70. Answer (3) Markownikov product. 71. Answer (1) Retention is dominating over inversion. 72. Answer (3) Saytzeff product. 73. Answer (1) Elimination of HCl resulting the formation of cyclic ether.
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74. Answer (2)

Cl NH2 Cl NH3
Benzyne

NH2 NH2 Cl Cl HNH2 NH2

NH2
.

Cl

75. Answer (4)

aq KOH C2H5Br alc

C2H5OH (1) CH2 = CH2 (2)

C2H5OH and CH3OCH3 are isomers


H C2H5OH CH2 = CH2 .
+

76. Answer (3) NO2 group is electron withdrawing it show I & R effect. More over it stabilize anion more than other group. 77. Answer (1) Inversion product. 78. Answer (1) NO2 at o and p position stabilize anion

NO2

F + OH CH3 NO2

NO2

F OH

CH3 NO2

O2N

F OH CH3 NO2

79. Answer (3) Iodoform test. 80. Answer (1) NO2 group show I & R effect. 81. Answer (4)

I + I2 + HI .

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82. Answer (3) SN1 reaction carbocation formation. 83. Answer (2)

OH Br AgOH Br
84. Answer (4) Depends on formation of free radical
Br2 (1 eq) h

Br

Br
.

Isomeric monobrominated product

Br2 h

85. Answer (4) Carbene formation then ring expansion takes place. 86. Answer (1) Due to presence of benzylic group

CH2Cl Cl
87. Answer (3)

NaOH Cl

CH2OH

O CH3O CH3OH CH2 CH2 C H2O/H


+

CH3CH2SH
88. Answer (3)

CH3CH2S

CH3CH2SCH2CH2O

CH3CH2SCH2CH2OH .

SN1 involves cyclic formation and

RO S=O Cl

+ R

O S=O Cl R Cl + SO2

CH3
Where R =

C H D

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89. Answer (4)

Br OH OH

O H

O
90. Answer (4)

O H

H CH3 CH = C COOH

Br Cl

H CH3 CH C COOH

2 chiral carbon
91. Answer (2)

Cl Br therefore 4 stereoisomers

Chlorination takes place at more probable free radical site. 92. Answer (1)

CH3 C CH2 O

H2O H
+

18

CH3 H3C C CH2 OH H2 O


18

Stable carbocation

CH3 CH3 C CH2OH O H


93. Answer (1)
18

CH3 CH3 C CH2OH O 18 H H

(CH3 )3 C Stable carbocation.


94. Answer (3)

H O N O O
less stronger than

H O

N O
Intramolecular H-bonding.

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95. Answer (1)

O C O + 2 C O

OH H OH

O C O C + H2O

OH

(phenolphthalein)
96. Answer (1)

COOH + NaHCO3

COONa + CO2 + H2O

Phenol does not react with NaHCO3. 97. Answer (3)


AgNO 3 AgI ppt. R O R + HI R OH + RI

98. Answer (1) Depends on electronegativity of elements and stability of conjugate pair. 99. Answer (3) Due to presence of intramolecular H bonding in (a). 100. Answer (4) Depends on pKa value

1 pKa Strength of acid


101. Answer (3) E1 Saytzeff oriented product. 102. Answer (3) Ring expansion
CH2OH H /
+

CH2 H

103. Answer (3) Both NaBH4 and LiAlH4 reduces acid chloride to alcohols. 104. Answer (3)

OH NO2 is weaker acid than H CO . 2 3

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105. Answer (3)

OH + FeCl3 O Fe O O + HCl

(ferric phenoxide) or (C6H5O)3Fe H2O [Fe(C6H5O)3(H2O)3]Cl3 Soluble complex


106. Answer (3)

CH3

CH3 KMnO4 3 2 OH CH3COOH H OH CrO3

CH3 OH O

107. Answer (3) THF is good solvent for Grignand reagent. 108. Answer (2)
CH2OH CH2OH PCl5 CH 2Cl CH 2Cl
+

+ POCl3

109. Answer (4)

H OH

Br2 CCl4
Trans (anti addition)

Mesoform (1) Racemic mixture d, l form

F Br2 cis anti addition

Mesoform + d, l = 3 stereoisomer 1 2
110. Answer (1) Ether have low boiling point, more volatile whereas alcohols due to presence of intermolecular H bonding have high boiling point therefore less volatile.

CH3 CH3OCHCH3 CH3 HI SN2 CH3I + HO CH CH3 NaOI CH3COONa + CHI3


(yellow ppt)

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111. Answer (2)

O H
+

CH2OH

CH3 OH
112. Answer (1) O

C OH C OH O

HO CH2 HO CH2 A H2SO4 O O

O O

HO CH2 CH2 HO
113. Answer (2)

A Base abstract acidic H. B Carbocation formation due to H+ ion. 114. Answer (1) B is primary alcohol and C is secondary alcohol. Primary alcohol produces carboxylic acid and secondary alcohol produces ketone. 115. Answer (2)

OH CHCl3 KOH
Reimer Tiemann reaction

OH CHO 50%KOH
Cannizzaro reaction

OH COOK +

OH CH2OH
.

116. Answer (1)

C6H5CO3H

O (A)

HBr

OH Br

Trans 2-Bromocyclohexanol

117. Answer (4)

CH3
Compound -1

CH2 = CH O CH CH3

H2O H
+

CH3 CH3CH2OH + CH3 C OH H

CH3
Compound-2

CH2 = C O C2H5

H2O H
+

CH3 CH3 C OH + C2H5OH H

Both 1 & 2 gives same product.


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118. Answer (1)

C6H5 CH2 CH2 CH2 OH (X) LiAlH4 (reduce both C = C and C = O bond) C6H5 CH = CH CH = O
crotonaldehyde

NaBH4 (does not reduce C = C bond

C6H5 CH = CH CH2OH (Y)

119. Answer (4) CH3OH < CH3 O CH3 < C6H5OH. 120. Answer (3) Jones reagent oxidies 1 alcohol to aldehyde

CH2OH

Jone's reagent

CHO

In choice (4), tertiary alcohol is resistant to oxidation at room temperature. R X + N a OR R O R + NaX. 121. Answer (2) Order of boiling point of isomeric alcohols 122. Answer (2) 3 > 2 > 1.
+

O + O
123. Answer (4) Cross Cannizzaro reaction

O O O O

HCHO is always oxidised to HCOOH other part reduced to alcohols. 124. Answer (4)

C OH + [(CH3)3CO]3 Al
125. Answer (1)

>C=O

CHO

KOH 50%

COOH +

CH2OH

no hydrogen atom Undergo Cannizzaro


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126. Answer (2)

OH CH3 CH = CH CH CH3
127. Answer (2)

O H2CrO4 in aq acetone (Jones reagent) CH3 CH = CH C CH3

CHO (CHOH)4 CH2OH


128. Answer (2) (A) Br is good leaving group and carbocation stabilize by allylic resonance. (C) Nucleophilic attack fastest at 129. Answer (1) NaBH4 reduces only carbonyl compounds. 130. Answer (2) Only acid bromide and alkyl bromide undergo hydrolysis with alkali Br attached with benzene ring is resonance stabilize therefore it give substitution at temperature and pressure. 131. Answer (4)
CO due to presence of H.

5HIO4

5HCOOH + HCHO

COOH HO CH2 CH NH3


132. Answer (3) is most acidic so pH is low.

R C=O + H HO
+

RC=OH OH

R C OH OH
133. Answer (3)

CH3 CH3CH2CH2 C N CH3MgI CH3 CH2 CH2 C = NMgI H3O


+

CH3 CH3 CH2 CH2 C = O + Mg I OH


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134. Answer (4)

O CH3 C Cl
135. Answer (4)

O H2S [H S H] CH3 C SH + HCl

O CH3 C O CH3 + CH3 Mg Br O MgBr CH3 C O CH3 CH3 H2O O CH3 C CH3
(1) CH3MgBr (2) H3O
+

+ MgBr + CH3OH OH

OH CH3 C CH3 CH3


136. Answer (2)

O H O CH2 C OH
137. Answer (3)

O SOCl2 Cl CH2 C Cl CH3OH

O Cl CH2 C OCH3

O CH3 CH2 C NH CH3

It should be noted that acid will be neutralised with amine. 138. Answer (2) keto acid undergo decarboxylation fast due to formation of resonance stabilised carbanion.
PhCOCH2COOH PhCOCH3.

138(a). Answer (3)

IIT-JEE 2008

O Ph

O OH

O
CO2

O
I2 + NaOH

C Ph E

CH3

iodoform reaction

C Ph

ONa + CHI3 G

-keto acid
139. Answer (4)

HIO4 can oxidise only two adjascent oxygen containing carbon atoms. Aldehydic and 2 alcohol oxidise to formic acid whereas 1 alcohol to aldehyde by periodic acid.
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140. Answer (2)

O + (H Br) O
141. Answer (1) Baeyers villiger oxidation. 142. Answer (3)

OH H
+

OH Br

OH

H Br O O OH

Br

O NH2OH H
143. Answer (2) HVZ followed by elimination. 144. Answer (3)
+

NOH Na/C2H5OH

NH2 H CH3

Ethylene glycol is protecting group for carbonyl. 145. Answer (3) (A) NaBH4 reduces cabonyl group. (B) HBO changes alkane to alcohol. (Anti-Markownikovs product) 146. Answer (4) Pinacol - pinacolone rearrangement. 147. Answer (1)

(1) O (2) O Anti - aromatic

Stable aromatic

(3)

Stable aromatic

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148. Answer (4)

Br NBS Mg dry ether

MgBr

CH3CN H3C C = O H3C C = N MgBr H2O


149. Answer (1)

CH3CH2COOH

Br2 Red P

CH3CHCOOH Br

NH3

CH3CHCOOH NH2

150. Answer (1)

O NH2 O H H N C CH2Cl

+ Cl C C Cl H AlCl3 H N O or N H
151. Answer (1) Coupling occurs prefenertially in the para position to the hydroxyl group. But it this position is blocked then coupling occurs at ortho position. 152. Answer (3)

C=O CH2

NO2 Br2/FeBr3

NO2 NaNO2 Br (X) HCl 280 K

N2Cl Cu powder Br (Z)

Cl

(W)

Br Mg Ether

Cl CH3 C6H5 OH (F) C6H5COCH3 H3O


+

Cl

MgBr (A)

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153. Answer (2)

NaNO2 NH2 HCl N2Cl

OH

phenanthrene
154. Answer (1)

KCN OH Cl OH CN

SOCl2 Cl CN

H2/Pt Cl CH2 NH2

NaOH HCl N

155. Answer (2)

NH3 O OH O A NH2

KOH Br2 NH2 B

CHCl3 KOH NC C H3O


+

(B & D are same] NH2 D

+ HCOOH E

156. Answer (1)

NMe2 NaNO2/HCl 0 5C

NMe2 H2/Ni

NMe2

NO2
157. Answer (2)

NH2

N2Cl

NH2

Hoffmann elimination takes place, resulting the formation of less substituted alkene. 158. Answer (1)

O CH3 C H gives iodoform (haloform) test.


159. Answer (3)

O SOCl2 CH3CH2COCl A (CH3CH2CH2)2NH CH3 CH2 C N B

C3H7 C3H7

CH3CH2COOH

LiAlH4

(C3H7)3N C

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160. Answer (2) Less substituted alkene is more stable

N CH3

CH3 OH CH3

H2O CH3 N

CH2 + H2O CH3

161. Answer (3)

CH3 H3C H

C NH2 + O = C C CH3 CH3 CH3 H3C H H H

C N = C C CH3 CH3 H2/Pt H CH3 C N CH2 CH(CH3)2 CH3 H


162. Answer (3) III - 2 lone pair of electrons present on 2 N atom. IV - Presence of SO2NH2 group. 163. Answer (4) Due to presence of +I effect of methyl group. 164. Answer (2) Formation of quaternary ammonium salt. 165. Answer (1)

OH O + H
+

OH
N H

N H OH2 N H N

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166. Answer (3) Only benadryl is tertiary amine Choline - quaternary ammonium salt

Benzedrine - primary amine Coniine 167. Answer (2) 2 amine react with Hinsberg reagent which forms insoluble material which does not soluble in NaOH. 1 amine react with Hinsberg reagent and finally form soluble complex. 3 amine does not react with Hinsberg reagent. 168. Answer (2) - secondary amine.

NH CH3I CH3 N CH3 I AgOH CH3 N CH3 OH AgOH CH3 N CH3 CH3 CH3I excess CH3 N CH3 I

169. Answer (2)


N H 2 O2 + NH2OH

170. Answer (1)

O O C O
171. Answer (3)

O C + NH3 C O OH NH2

O C NH2 H2/Pd. high pressure CH2NH2 H2/Pd. CH2NH2

H2 reduces CONH2 and then benzene ring.


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172. Answer (3)


H2O R N = C = O RNH2 + CO2 .

173. Answer (2) Nitroglycerene is formed by reaction of glycol (alcohol) and nitric acid (acid). 174. Answer (4) Secondary amine has + I effect. 175. Answer (2) NaBH4 reduces only carbonyl compound where as LiAlH4 reduces carbonyl and cyanide group. 176. Answer (3)

NH2 NH3 CH3 OH

177. Answer (1)

O HN O

H N O H H O OH

O N O

H N O H H O

Anion (conjugate pair) stabilize by resonance. 178. Answer (1)


LiAlH4 H3O CH3 C N CH3 CH2 NH2 CH3 CH2 NH3 .
+

179. Answer (2)

O CH3 H Pyridine O H3C H C = N . NH C NH2 Semi carbazone


O

C = O + H2 N NH2 C NH2 semi carbazide

NH2 of C NH2 does not undergo condensation due to its resonance stabilization.
O C NH2 O C = NH 2

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180. Answer (3) 1 amine oxidise to nitro group and 2 alcohol oxidise to ketone with cold KMnO4. 181. Answer (4)

NH2OH H Et OH
+

OH

OH

H2NOH H

OH N OH H
H2O

NOH
182. Answer (2) NaOH react with carboxylic acid. 183. Answer (4) 3 amine cannot form amine oxide. 184. Answer (3) Due to stability of carbocation. 185. Answer (2)

N OH H

CH3 CH3 CH2 C C = O + H2NCH3 H H CH3 H CH3 CH2 C C = N CH3 H H2/Pt. CH3 H H

CH3 CH2 C C N CH3 H H

186. Answer (3) Nylon has strongest intermolecular forces (i.e. hydrogen bonding) out of these. 187. Answer (1) Artificial silk is a polysaccharide while the other three are polyamides. 188. Answer (1)

CH3 n CH2 = C CH3

CH3

CH3

C CH2 C CH2 CH3 CH3

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189. Answer (4)

F
Teflon

F
is fully fluorinated polymer.
n

C C F F

190. Answer (3)


Amino acid are amphoteric in nature. The acidic properties are due to amino group N H3 .

191. Answer (1) Alanine is NH 2 CH COOH


CH3

CH3 (At low pH) i.e. acidic pH NH3 CH COOH


192. Answer (1)

CH3 (At high pH) i.e. basic pH NH2 CH COO

During vulcanization of natural rubber S S crosslinks are formed which make it more elastic. 193. Answer (3)
n CH2 = CH2 343 K 373 K, 6 7 atm Ziegler Natta catalyst [TiCl4 + (C2H5 )3Al] ( CH2 CH2 )n

194. Answer (3) The -helix is known as 3.613 helix since each turn of the helix has approximately 3.6 amino acids and 13 membered ring is formed by hydrogen bonding. 195. Answer (4) Both insulin and carboxy peptidase contain Zinc. 196. Answer (3) Cashmilon is polyacrylonitrile. 197. Answer (4)

COOH
Proline is heterocyclic amino acid. H N

amino acid have a primary amino group except proline. 198. Answer (3) Acrilan is PAN (Poly acrybonitrile). 199. Answer (4)

H N O

Caprolactum is monomer of Nylon-6 or Perlon


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200. Answer (1)

OH
Bakelite is made up of (phenol) and HCHO (formaldehyde)

OH + HCHO

H2C

OH

CH2

CH2
201. Answer (1)

Methoxy group is attached with carbonyl oxygen. 202. Answer (2) There is a hydroxyl group and an ether attached to the same carbon forming a hemiacetal. 203. Answer (1) OH group present on right side

OH CH2OH

204. Answer (1) Fat 130 ATP, carbohydrate 38 ATP, protein 5 ATP. 205. Answer (1)

CH2OH H OH OH H
206. Answer (2)

O H H OH OH

D glucopyranose

CHO CHOH (CHOH)3 CH2OH


C6H5NNH2 H2O

CH = NNHC6H5 CHOH (CHOH)3 CH2OH


C6H5NNH2 C6H5NH2, NH3

CH = NNHC6H5 C=O (CHOH)3 CH2OH


C6H5NNH2 H2O

CH = NNHC6H5 C = NNHC6H5 (CHOH)3 CH2OH glucosozone

207. Answer (2) Only phospholipids form bilayer memberane.


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208. Answer (2)


+

C12H12O11 + H2O sucrose ( )D = +66.5

H invertase

C6H12O6 C6H12O6 D(+)-glucose + D()-fructose ( )D = 52.7 ( )D = 92.4 invert ( )D = 19.9

209. Answer (3) C12H22O11 + 18[O]


conc. HNO3

COOH + 5H2O COOH oxalic acid

210. Answer (2) The excess glucose present in the blood is transported in the tissue where insulin converts it into glycogen. The deficiency of insulin causes diabetis. 211. Answer (2) Proteins give ninhydrin and molisch test. 212. Answer (3)

C12H22O11 + H2O ( )D = +66.5

H invertase

C6H12O6 + C6H12O6 D(+)-glucose D()-fructose ( )D = 52.7 ( )D = 92.4 invert sugar ( )D = 19.9

213. Answer (1) Glucose and fructose are functional isomers. 214. Answer (1) Glucose and fructose have similar configuration on C3, C4 and C5 so they form same osazone. In osazone only C1 and C2 are involved. 215. Answer (4) -D-glucose and D-glucose are anomers. 216. Answer (3)
O H

CN

peptide bond of protein form Hbond.

217. Answer (2) Stearic acid, Palmatic acid and Oleic acid are higher fatty acids. Their Na salts are used as soaps. 218. Answer (2) Chemical name of vitamin E is tocopherol. 219. Answer (3) Purines contain two rings in which each ring contains 2 nitrogen atoms.
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220. Answer (4) Denaturation of protein converts quaternary, tertiary and secondary structure to primary structure. 221. Answer (2) Invertase for carbohydrates, urease for urea and trypsin for protein. 222. Answer (4) pH = 1 (acidic). It accepts a proton and exist as cation NH3 is acidic group. 223. Answer (3) Amide linkage ( CONH2) 224. Answer (4)

CH2OH H
5 Chiral carbon present in Dglucose

* HO

* H OH * H

O H * OH

OH * H

225. Answer (3)

CN HC=O (CHOH)4 CH2OH HCN H C OH (CHOH)4 CH2OH H3O


+

COOH (CHOH)5 CH2OH HI COOH (CH2)5 CH3 Heptanoic acid

226. Answer (3)

CH2OH C= O CH2OH
No chiral carbon No stereoisomers. 227. Answer (2) Ruff degradation.
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Organic Chemistry

Section - B : Multiple Choice Questions


1. Answer (1, 2) In cis form same groups are present on the same side of double bond. 2. Answer (1, 2, 3, 4)
+
+

In

and

aromaticity is maintained in canonical forms, while benzyl carbocation looses its

aromaticity in canonical forms. (CH3)3C is more stable than benzyl carbocation due to 9 hyperconjugative bonds.
+
+

CH2

is more stable than benzyl carbocation due to bent p-atomic orbital.

3.

Answer (2, 3) If one + I and one I effect group is present on both doubly bonded carbon atom then the dipole moment of trans form is more than cis form.

4.

Answer (1, 2, 4) Beleistein test is not given by those compound in which F atom is present. Urea and thiourea also give Beleistein test.

5.

Answer (1, 3)

COOH OH
is more acidic than HCOOH due to ortho effect while

COOH
and

COOH

are less acidic

CH3
than HCOOH. 6. Answer (1, 2)

O O H H C C C C O Conjugate base of maleic acid Conjugate base of fumaric acid O

H , HOOC

C C

C H

OH

(stability)

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7.

Answer (1, 3)

F F

SbF5

SbF5

Aromatic systems

8.

Answer (1, 2) Triple bond is more prone to hydrogenation.

9.

Answer (1, 2, 4) Cyclooctatetraene has no planar structure.

10. Answer (1, 2, 3, 4) C4H10O can form 4 alcohols & 3 ethers which can exhibit chain, position, functional & metamerism. 11. Answer (2, 4) (2) and (4) contain chiral carbon so are optically active. 12. Answer (1, 2, 3) A, B, C, D are isomers of same compounds where (A) and (B) make, enantoimeric pair and (C), (D) make another enantiomeric pair. 13. Answer (1, 2)

COOH H2N H 2 3 H OH

S R H H

COOH 2 3

R OH S OH

CH3
14. Answer (2, 3, 4)

COOH

(1) molecule contains 3 (1 H), 8 (2 hydrogens) and 3 (3 hydrogens). 15. Answer (1, 3, 4)

O has no acidic hydrogen to participate in enol formation.

16. Answer (1, 2, 3) Bromination takes place at most stable free radical. 17. Answer (1, 2, 3)

ROH + CH3MgI CH4 + Mg 0.37 x x = 74


H CH3 C CH2OH CH3
H
+

I O R

112 cc 22400

CH3 C = CH2 CH3

O3

CH3 C = O + HCHO CH3


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18. Answer (1, 3) A Presence of benzylic H B Absence of benzylic H 19. Answer (1, 3)

CH3
C5H12 + Cl2 H3C C CH2Cl
Na Wurtz reaction

CH3

CH3

H3C C CH2 CH2 C CH3 CH3 (C) CH3

CH3 (B)
20. Answer (1, 2)

O O H O O
O3

C C O

CHO CHO

H O H O H O

H O

21. Answer (1, 2, 3) Wurtz reaction is a type of free radical reaction.


dry ether C2H5 Cl + 2Na + Cl C2H5 C 4H10 + 2NaCl

butane

Ethyl free radical can disproportionate to give ethane and ethene.


2 C 2 H5 C 2H4 + C 2H6
Ethene Ethane

22. Answer (1, 2, 4)

CH3
On applying selectivityreactivity principle, only CH3 CH CH CH3 has about 35% in the mixture. Others have less than 35% in the mixture. 23. Answer (1, 3, 4) 2-methyl 2-butene is more stable than but-2-ene due to presence of 9 hyperconjugative bonds, while but-2-ene contains 6 hyperconjugative bonds. Buta-1, 3-diene and 2-methyl buta-1, 3-diene are more stable than but-2-ene due to conjugation. 24. Answer (1, 2, 4) In all molecule, one H2 molecule is added but only (1), (2) and (4) can give symmetrical diketone on reductive ozonolysis, while (3) give only ketone. 25. Answer (1, 3, 4) In presence of 1% alkaline KMnO4, C6H5CO3H and OsO4/OH, syn addition occurs while in presence of HCO3H, anti addition occurs.
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Cl

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26. Answer (1, 3) A by E2 elimination, B by E1 elimination. Alc. KOH will undergo dehydrohalogenation by anti elimination. 27. Answer (1, 4) NBS characteristic reagent for allylic bromination Br ortho para directing 28. Answer (1, 2)

Br
NBS

(A)
29. Answer (2, 3) Due to presence of unsaturation. 30. Answer (1, 2, 4)

Cl

anhyd AlCl3 hydride shift more stable carbocation

31. Answer (2, 3) will give only 1 mono halo substituted derivative.

will give 3 mono halo substituted derivative. 32. Answer (1, 3) SO2Cl2 and Cl2 replaces benzylic H. 33. Answer (2, 3) C3H7Br + AgNO2 C3H7NO 2 + C3H7 ONO
major minor product

due to ambident nucleophilic nature of nitro group. 34. Answer (1, 3)

CH2
LiAlH4

CH3

H3C

Br

CH3 (A)
CH3
LiAlH4

CH3 Br H2C H3C

(B)
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35. Answer (1, 2, 3, 4) All are feasible reaction (1), (2) substitution as well as elimination (3) Ring expansion (4) Ring contraction 36. Answer (1, 2, 3, 4) 1-4 addition dominates at high temperature and with excess of HBr both double bond give addition product. 1-2 addition dominates at low temperature 37. Answer (1, 2, 4)

Br
HNO3

Br NO2 Br Br

Br

Br

Highest melting point 1, 3, 5 tribromobenzne. 38. Answer (2, 4) (2) R Br + Ag 2O R O R + AgBr


dry

H2SO4 CH3 CH2 O CH2 CH3 (4) CH3CH2OH 413 K

39. Answer (1, 2, 3) In (1), (2) and (3) options, stable carbocation is formed as an intermediate, so, these give SN1 mechanism, while CH3Cl mainly gives SN2 mechanism because it is 1 alkyl halide and produce less stable carbocation. 40. Answer (1, 3) (1) and (3) on E2 elimination give an alkene but (2) and (4) cant give an alkene 41. Answer (2, 3) 3 alkyl halide mainly gives SN1 mechanism. Polar protic solvent favours SN1 mechanism while polar aprotic solvent favours SN2 mechanism. 42. Answer (1, 3, 4) In (2) option, alkene is formed as major product while in other options, ether is formed as major product. 43. Answer (3, 4)
Pyridine CH3CH2CH2OH + SOCl2 CH3CH2CH2Cl + SO2 + HCl

CH CH CH Cl + POCl + HCl CH3CH2CH2OH + PCl5 3 2 2 3

44. Answer (1, 2, 3) (1) Yellow ppt of AgI (2), (3) Iodoform CHI3 formation 45. Answer (1, 3) (1) Friedel Craft alkylation (3) Friedel Craft decarbonylation
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46. Answer (1, 2)


H H2O
+

+ major minor product

OH
47. Answer (3, 4) (2) RNH2 + CHCl3 + alc.KOH RNC + KCl + H2O

NH2
(4) + CHCl3 + alc.KOH

NC
+ KCl + H2O

48. Answer (1, 2, 4) 1, 2, 4 gives Hoffmann product (1) Hindered base (2) EICB (stable conjugate base) (4) Hoffmann elimination 49. Answer (2, 3)

H
H

C N

is o, p directing due to N group.

50. Answer (1, 3) Only 1 amine gives carbyl amine test. 51. Answer (1, 2) cis and trans isomers 52. Answer (1, 2, 3)
Ph H C=C H Ph & Ph H C=C Ph by elimination. H

CH2 Br 1 3

2 + CH2
Br

1 CH2 OH
HOH + H

CH2

CH2 H5C2

H5C2

H5C2

H5C2 (2)

H5C2
H
+

HOH

HOH

CH2

CH2 OH

H5C2 OH (1) H5C2 (3)

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53. Answer (2, 3, 4)

Br
C2H5ONa

54. Answer (2, 3, 4)


HI/P

OH
55. Answer (1, 2) Water favours the formation of a polar compound. 56. Answer (1, 4)

OH
Secondary alcohol containing 57. Answer (2, 4)
16

CH

CH3 linkage can give all given three reactions.

16

O H
18

16

OH

OH

H2O

18

58. Answer (1, 2, 3, 4) In (1), (2) and (3) intramolecular hydrogen bonding is present. 59. Answer (1, 2, 3)
OH

Iodoform test is given by alcohols having the group R CH CH3 . Thus, all the three except (4) give this test. 60. Answer (1, 3)

(i) NaNH2 H2 CH3 CH2 C CH CH3 CH2 C C C2H5 Pd/BaSO (ii) C2H5Br 4 (X)

H5C2 C =C H cis alkene (Y)


KMnO4 alk.

C2H5 H

C2H5 H H C2H5 meso compound optically inactive (Z)


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OH OH

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61. Answer (1, 3) CH3COCl and (CH3CO)2O can be used. 62. Answer (3, 4) Both (3) and (4) are stable due to intramolecular hydrogen bond formation

Cl

Cl C CH and F C CH Cl H O F H O

No hydrogen bonding occurs with Br and I due to large size and lesser electronegativity. 63. Answer (1, 3)

C6H5CHCH3 and CH3CH CH3 gives iodoform test due to presence of CH3 group adjacent to OH group. OH
64. Answer (1, 3) In option (1) and (3), most stable carbocation is formed as an intermediate. 65. Answer (1, 2)

OH

OH NO2
and

OH NO2
cant give effervescences with NaHCO3 but

OH O2N NO2
can

NO2
give effervescences with NaHCO3 due to more acidic nature. 66. Answer (2, 3)

NO2

HO C CH3 and H2N C CH3 cant give iodoform on warming with NaOH and iodine due to resonance.
67. Answer (1, 2, 4) Pyroligneous acid cotnains 9 10% CH3COOH, 2 4% CH3OH, 1 2% acetone and rest is water. 68. Answer (1, 2) In esterification, H+ of alcohol reacts with OH of carboxylic acid to form H2O and the reactivity of carboxylic acid is 1>2>3. Other statements are correct. 69. Answer (1, 2, 4)

OH NO2 NO2 ,

COOH
,

SO3H
are stronger acid than H2CO3 acid.

NO2
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70. Answer (2, 4)

O H H D CH = CH CH CH3
K2Cr2O7

H D

C OH O O

OH OH

+ HO C C CH3
SOCl2

O H D (X)
71. Answer (1, 2)
H H2O
+

C Cl + Cl C C CH3 O (Y)

OCH3

HO OH

+ CH3OH OH

H2O

O OH

72. Answer (1, 3) (3) does not contain hydrogen and (1) contains vinylic hydrogen which cannot be easily removed. 73. Answer (3, 4)

O O Cl CCl3

OH conc.

COO OH

aq. KOH

aq. KOH

COOC2H5 Br

74. Answer (1, 2, 3, 4)


R CHO
O H C OH
AgNO3/NH4OH
AgNO3/NH4OH

COO

HCO 3

NHOH
AgNO3/NH4OH

NO

(R can be CH3 C6H5)


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75. Answer (1, 3, 4)

CH

CH2
B2H6 H2O2/OH

OH
H2O2/OH

CH2MgBr
HCHO

CH2

CH2

OMgBr

MgBr +

76. Answer (1, 2, 3, 4)

O O O
Resorcinol Catachol Nitration Fluorisien Alizarin 2,4 D.N.P. Phenol

Phenolpthaline

77. Answer (2, 3) OMDM gives Markownikovs HBO gives Anti-Markownikovs product No, carbocation formation No, rearrangement takes place 78. Answer (1, 2, 3)

CH3
(1) H3C CH CH2 CHO
NaOH

CH3 H

CH3 C C C CHO H OH C H H3C CH 3 aldol

CH3

H
H3O
+

CH3

OH

(2) H3C CH CH2 C = O + CH3MgBr

CH3 CH CH2 C CH3 H

(3) 3-pentanone and 3 methyl butanol have same molecular formula (4) On Wolff Kishner reduction it gives 2 methyl butane.
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79. Answer (1, 2, 3)

O
(1) PhCH2MgBr + CH3 C H

OH CH3 C CH2 Ph H

O
(2) CH2 CH CH3 + PhLi
H3O
+

OH PhCH2 C CH3 H

O
H3O
+

OH PhCH2 C CH3 H

(3) Ph C C H + CH3MgBr

H 80. Answer (1, 2, 4)


CH3
(1)

(2)

CH3
(4)

CH3
81. Answer (2, 3, 4) (2) NaBH4 reduces carbonyl to 2 alcohol. (4) Silver mirror test given by aldehydes. 82. Answer (1, 2)

N2Cl
Cu/KCN

CN
H3O
+

COOH
NaOH CaO

(X)
83. Answer (1, 3)

(Y)

(Z)

OH
(1) H C CH3
(O) KMnO4

O C CH3

COCH3
(3)

+ CH3COCl

Anhy AlCl3

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84. Answer (2, 3, 4) CH3CHO is less reactive than HCHO but more reactive than ketones. 85. Answer (2, 3, 4) Ethyl alcohol is less acidic than phenol. 86. Answer (1, 3) Sulphur and quinoline

N
87. Answer (1, 2, 3) In (4) 2 alcohol is formed. 88. Answer (1, 2, 3) NaHSO3 is used to separate ketone and aliphatic methyl ketone as well as aldehyde and aliphatic methyl ketone. 89. Answer (1, 2, 3, 4) In (3) COOH group is reduced in preference to 90. Answer (1, 2, 3) Active methylene compounds are used in their reaction. 91. Answer (1, 2, 3, 4) (1) Cyanohydrin formation (2) Aldehydes give silver mirror (3) Cross aldol (4) Condensation with ammonia derivative 92. Answer (1, 2, 3, 4) (1) C2H5COOH (2) CH3CH2COOH

C = O group.

CH3 CH2COOH (3) CH3 CH2 CH2OH


(A) (B )

(4) CH3CH2COOH 93. Answer (1, 2, 3)

CH3 Cl CH3 CH3


KNH2

CH3 NH2

Cl CH3
KNH2/

CH3

CH3

NH2 Cl
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94. Answer (1, 4)

NO2
Fe/H2O(v)

NO

NH2
strong acid electrolysis

OH
95. Answer (1, 4)

NH2

HNO2

OH

But exceptionally methylamine forms ether. 96. Answer (1, 2, 3, 4) In all given compounds lone pair of N is resonance stabilized. 97. Answer (1, 2, 4) 3 amine has no H atom on N. 98. Answer (1, 3) Nylon66 =

[ NH (CH2)6 NH CO (CH2)4CO ]n

CH3
PMMA = CH2 C

COOCH3
99. Answer (1, 2, 3, 4) 100. Answer (1, 2, 3) Fact 101. Answer (2, 4) Fact 102. Answer (1, 2, 4) 103. Answer (1, 3, 4 ) 104. Answer (2, 3, 4)

Sucrose is a disaccaharides of glucose and fructose. 105. Answer (1, 3, 4) Nylon-66 is a copolymer monomers are hexamethylenediamine and adipic acid. 106. Answer (1, 2, 4) Natural silk is a polyamide. 107. Answer (1, 2, 4)

CH CH + HCN

Ba

+2

polymerisation

(PAN) CH2 CH CN
n

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108. Answer (3, 4) Fructose is equilibrium with glucose in alkaline solution and hence gives positive test of aldehydic group. 109. Answer (2, 4) At pH > 7, H+ from carboxylic acid will be lost. 110. Answer (1, 2, 3) Glycine is only amino acid which is optically inactive, since then is no asymmetric centre. 111. Answer (1, 2, 3, 4) 112. Answer (2, 3, 4) Guanine is purine. 113. Answer (3, 4) Remini and Schyrver are tests for formaldehyde. 114. Answer (3, 4) 115. Answer (1, 2, 3, 4)

Section - C : Linked Comprehension


C1. 1. Answer (4)

sp hybridised H H
3

So non planar (so not aromatic). sp hybridised

(I) 4 electrons (so not aromatic).


2. Answer (4)

N H

N H E
+

H E N H
E N H
+

N H

H E

+ E N H

H E N H

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3. Answer (2)

O +

O +

C2. 1. Answer (4)

anti aromatic

+ 1 group stabilises free radical. 2. Answer (2) Allyl carbocation is most stable. 3. Answer (1) Stability of carbanion increases with the presence of electron withdrawing group, whereas decreases with the presence of electron releasing group. C3. 1. Answer (1)

OH

Aromatic, hence very stable. 2. Answer (2) In (1), (3) & (4) the group attached to CO, involves,

O C
in resonance.

O Cl

O Cl
H

3. Answer (4)
O O O O

stabilised due to intramolecular hydrogen bonding. C4. 1. Answer (2) Electron releasing group decreases acidic nature hence highest pKa. 2. Answer (2) In aqueous solution 2 amine is more basic than 3 & then comes 1. 3. Answer (4) For iodine + R is least. C5. 1. Answer (1)
= 12 + 2 2 + 2 cos
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2. Answer (2) Symmetrical molecules have zero dipole moment. 3. Answer (1) CCl4 has zero dipole moment. As the number of chloride atoms increase dipole moment decreases. C6. 1. Answer (1)

CH2

2 1 no. of hyperconjugative structures = 3 Alkyl group make the ring electron rich by their tendency to make ring electron rich by hyperconjugation. 2. Answer (2) (3) is most stabilised by higher + 1 effect of isopropyl group. 3. Answer (3) CH = CH2
+

methyl shift

C7. 1. Answer (4)

[O] O3, H2O2


2. Answer (3)

COOH COOH
CH3

CH2 = CH2

MCPBA O

CH3MgI OMgI (A)

H3O

OH (B)

3. Answer (4)

O CH3CHO + + HCHO

C8. 1. Answer (1) Diels alder reaction involves (4 + 2) cycloaddition. 2. Answer (2)

H H H

H H

C=CC=C B

H H

Br

Br

Br

Br
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3. Answer (3)

+ B
C9. 1. Answer (1)

O3/H2O

COOH COOH

a is most substituted double bond, so most stable.

2. Answer (3) The structure has OH group on most substituted carbons of the double bonds because the water attacks the carbocation that forms. The most stable carbocation is the one on the most substituted carbon. 3. Answer (1) All of the double bonds have two substituents. If on the one end of the bond both the substituents are same. Consequently there is no possibility for geometric isomers. C10. 1. Answer (4) Alkenes are more reactive towards electrophilic addition reactions but when product formed is conjugated diene alkynes give this reaction first. 2. Answer (1) Alkenes are more reactive for electrophilic addition reaction. 3. Answer (1) Alkenes are more reactive for hydrogenation. C11. 1. Answer (4) Cis alkene + Anti addition Racemic mixture. 2. Answer (4) Product produced has no chance of having plane of symmetry.

H CH3
3. Answer (4) OsO4 H2 KMnO4 Br2/CCl4 C12. 1. Answer (2)

OH CH3

Syn hydroxylation Syn addition Syn hydroxylation Anti addition

Cl Cl Cl (d) + (l) Cl (d) + (l)

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2. Answer (2)

Cl

probability = 1 3 = 3

probability = 2 3.8 = 7.6

Cl

probability = 1 5 = 5

Cl

Cl
probability = 6 1 = 6 3. Answer (3) Bromination takes place at most stable free radical and free radical at bridge head carbon is least stable. C13. 1. Answer (3) Alkoxide ion is a better base and so will favour E2. 2. Answer (3) Same. 3. Answer (2) Vinyl halide and aryl halide have partial double bond character between carbon and halogen. in aniline, NH2 is a strong base and hence very weak leaving group, so cannot undergo SN reaction C14. 1. Answer (4)
OCH 3 is a better base.

2. Answer (1) SN1 3. Answer (3) E1 C15. 1. Answer (3)

W t. of used alkali (w) (M + 42 n) = 56 n t W . of acetyl derivatives (w)


M molecular mass of alcohol. 2. Answer (1) Secondary alcohol (glycol) gives formic acid. 3. Answer (1) Two 1 alcohol gives formaldehyde and C = O changes to CO2.
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OH
C16.

ONa NaOH (i) CO2 4 - 7 atm P A (ii) H


+

OH COOH NaOH CaO B (CH3CO)2O O COCH3 COOH E OH NaOH COONa + CH3COOH G H Br

OH

C Br2 OH Br

Br

1. Answer (2) 2. Answer (1) 3. Answer (3) C17. 1. Answer (2)

OH Br Mg ether CH3CHO MgBr H Br CH3


2. Answer (2)
C 3H 7 C H 3C Ph OH
+

CHCH3

Ring expansion Br

CHCH3

There would be a racemic mixture since carbonyl group is planar and can attack from both side. 3. Answer (3) Alkyl group (carbanion) attack on carbon atom of carbonyl group. C18. 1. Answer (2)

OH
Compound B is C7H6O3

H-bond C=O OH

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2. Answer (1)

OCOCH3 CH3COCl
OH COOH

COOH (C) (aspirin) OH

PhOH H
+

COOPh (D) (salol)

3. Answer (2) Compound D is salol. C19. 1. Answer (3)

OH B CH3
2. Answer (3)

O CH3 A =

O COCH3 Y
3. Answer (1)

COOH , Aspirin used as antipyretic.

OH & CH3
C20. 1. Answer (1)

O CH3 C7H8O

O CH3
Carbanion becomes aromatic. 2. Answer (1)

O H2C H H2C

O H

Carbanion stabilize by resonance.


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3. Answer (1)

H H3C C OH NaOI COONa + CHI3

C21. 1. Answer (3)

NH2 HNO3 H2SO4

NH2 + NO2 M (47%)

NH2

NO2 P (51%)

Metal is formed due to formation of anilinium ion as intermediate because of basic nature of aniline. 2. Answer (2) The carbonyl group in electron withdrawing making the amide less basic than the amine. 3. Answer (2) The substitution is para, so the amide must be ortho-para directing. The best explanation for the lack of ortho substitution is steric hinderance. C22. 1. Answer (3)

Ag2O NMe3I
2. Answer (2)

OH

+ NMe3 + H2O

N (CH3)3

Me 3CH3I CH2NH2 CH2 N Me Me Ag2O

+ Me3N + H2O
3. Answer (4)

N Me OH nBu Et

CH2 = CH2

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C23. 1. Answer (1) Due to ortho effect. 2. Answer (2) Conjugate base stabilise more than other site. 3. Answer (2) Conjugate pair stabilise by resonance. C24. 1. Answer (3)

O A
2. Answer (2) Phenyl group migrated over to N atom. 3. Answer (2) R N = C = O is common in Schmidt and Hoffmann reaction. C25. 1. Answer (3) The lone pair of electrons on the nitrogen of the amine attacks the electrophillic carbon of acid. 2. Answer (1) Hbonding in Nylon. 3. Answer (4) It is prepared by condensation of adipic acid and hexamethylene diamine. C26. 1. Answer (1)

CH2NH2

due to ring expansion.

O H
H bonding

CN
2. Answer (2) Teflon is polymer of CF2 = CF2. 3. Answer (3) Polyacrylonitrile

H H

H CN

H H

H CN

C=C

( C C )n

C27. 1. Answer (2)


pH = 3.30 + 8.70 =6 2

2. Answer (4) Amino acids show lowest solubility at isoelectric point since there is highest concentration of the dipolar ion. 3. Answer (4) Since it is basic amino acid with 2NH2 group, So pH must be greater than 7.
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C28. 1. Answer (2) Shortening of carbon chain of one carbon. 2. Answer (3) Name of reaction Ruff degradation. 3. Answer (4) (A) (B) Pentyacetate (D) Aldopentose

C = NOH ,

(C) Cyanide, C29.

Starch (C6H10O5)n

H 2O

C12H22O11 (C)

H 2O

C6H12O6 (D)

conc. H2SO4

(E) Black

200 250C

(C6H10O6)n (A) Dextrin


1. Answer (2) 2. Answer (1) 3. Answer (1) C30. 1. Answer (3) Elimination dominates over substitution. 2. Answer (4) A C3H6 B CH3 CH CH3
Br

C CH3 CH CH3

OH
3. Answer (3) Substitution product

Cl

OH

OH

C31. 1. Answer (1) OH

O (O) RCR

RCR OH 2. Answer (4)

All of these contain Cr+6

PCC N
3. Answer (3) nfactor = 6

CrO3 Cl

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C32. 1. Answer (3)

O C2H5 C C2H5 + C2H5MgX


H3O
+

OH C2H5 C C2H5 C2H5


H2O

H C2H5 C = C CH3 C2H5 O C2H5 C = O + CH3 C H C2H5

2. Answer (3) Less hindered more reactive 3. Answer (3)


C=O sp
2

C sp
3

C33. 1. Answer (3)

CH3
H2SO4

CH3 SO3H
PCl5

CH3 SO2Cl
NH3

CH3 SO2NH2

CH3 COOH
H2SO4

SO2NH2 SO3H (P)

CO NH SO2
2. Answer (1)

CH3
PCl5

CH3
NH3

CH3
(i) ClOH (ii) NaOCl

CH3

Cl SO2NNa
+

SO3H
3. Answer (4)

SO2Cl

SO2NH2

CH3
PCl5

CH3
C6H5OH

CH3
H2O
18

CH3 +
18

OH

SO3H

SO2Cl

SO2 OC6H5 ester

SO2OH

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C34. 1. Answer (2) Rearrangement of carbocation. 2. Answer (3) Intermediate 2 carbocation of A Intermediate 1 carbocation of B 3. Answer (3)

OH OH CH2NH2
C35. 1. Answer (2) O

OH ring expansion

OH

HNO2 H N2
+

CH2

O & CH2 C H

CH2 C CH3

4 product 2 carbanion 2. Answer (4) Carbanion stabilize by resonance. 3. Answer (4) (1) & (2) option no H atom (3) option give chloroform reaction.

Section - D : Assertion - Reason Type


1. Answer (1) That acid is easily decarboxylate which produce most stable carbanion. 2. Answer (1) Due to I effect producing group. 3. Answer (1)

+ CH O C H CH O = CH 2 3 2 3 Minor Major
Stabilize by resonance, the second structure has octets on all atoms and an additional bond. 4. Answer (3)

HONO2 + H2SO4 base


5. Answer (2)

H O NO2 + HSO4 H

acid

HOX + H (acid)

HOX H

H2 O + X electrophile

6.

Answer (2) The bond energy of allylic carbon hydrogen bond in propene is less than the bond energy of benzylic carbonhydrogen bond in toluene.

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7. 8. 9.

Answer (3) Hyperconjugation increases stability of carbocation and free radical, not carbanion. Answer (1) N does not have vacant d-orbital for expansion of octet. Maximum co-valency of N is 4. Answer (3) Tartaric acid isomers = 3. d, l and meso form.

10. Answer (2)

O H2O/H or OH
+

OH (1-5 migration of H atom) . NH2

NH2
11. Answer (3) 1 is R, II S. 12. Answer (1)

H-bonding Cl Cl C Cl H
13. Answer (2) No. of isomers 2n 2 14. Answer (3) Double bond generating geometrical isomers and chiral centre give optical isomers. 15. Answer (2) Unimolecular 16. Answer (4) A CHCl3 is more acidic than CHF3 because Cl3C is less basic than F 3C because fluorine can disperse charge only by an inductive effect while Cl disperse charge by inductive effect as well as p p bonding delocalisation. 17. Answer (1) Due to steric crowding electrons pair does not undergo resonance. 18. Answer (4) Triplet carbene is more stable than singlet carbene. 19. Answer (1) Angle strain of cyclopentane =
109.5 108 = 0.75 (negligible). 2
n 1 2 .

O CH O

elimination.

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20. Answer (1)

CH3 CH3 C
21. Answer (2) Vinyl chloride does not form vinyl carbocation with anhy. AlCl3. 22. Answer (3) Pyridine is less reactive than benzene towards EAS creating at the position due to - I effect of the N-atom while in pyrrole the non-bonding pair on nitrogen is part of aromatic rextet. 23. Answer (1) Number of hyperconjugative structure stability. 24. Answer (3) Acidic hydrogen is present in 1-alkynes but not in alkyne-2. 25. Answer (2) Due to (1 4) position of H which causes hinderance in boat form. 26. Answer (1)

CH3 O CH3

CH3 C

O CH3

(resonance)

OH H H H
27. Answer (4)

H-bonding

OH H

Ethylene is more reactive than acetylene towards electrophilic addition reaction. 28. Answer (4) Rate of nitration of C6H6 = rate of nitration of C6D6. 29. Answer (1)

Br Intermediate

CC
bromonium ion

ion

30. Answer (2) Correct R Mesotartaric acid has molecular symmetry. 31. Answer (4)
Hg
+2

Hg

Hg

CH3 C C H

H3C C ==== C H O H H

CH3 C = =CH O H H

Hg

+2

CH3 C = = CH2 OH (enol)

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32. Answer (2) (II) Does not react with NH3 since double bond is not polarised by an electron withdrawing group.

CH3 H
(I) Form product 33. Answer (3) Alkyne gives carbonyl compounds
RC CH
(i) H2O(BH3)2 THF (ii) H2O2/OH
+

O
intermediate.

(III) Via H3N C C C = =C

CH3 H

CH3

R CH2 C H O

34. Answer (4) It involves formations of vinyl carbocation, which is unstable reaction does not takes place. 35. Answer (1)

OH ring expansion H
+

36. Answer (3) Order of boiling point Straight chain > branched chain of isomeric hydrocarbon. 37. Answer (1) Removal of Cl is easy due to presence of NO2 group. 38. Answer (4) Anti-Markownikov product. 39. Answer (4) Chloroform is heavier than water. 40. Answer (1) Racemic mixture is obtained due to walden inversion. 41. Answer (4) C2H5Br + AgCN C2H5CN (major product) 42. Answer (2) Aniline behaves as Lewis base for anhydrous AlCl3. 43. Answer (3) Addition of HBr to 2-pentene give meso product.
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44. Answer (3) 2 carbocation converts to 3 carbocation. 45. Answer (1) HCN is weak acid where as HI is strong. 46. Answer (3) Presence of electron withdrawing group at ortho position of Aryl halide increases nucleophilic substitution. 47. Answer (3) Correct reason :- In aryl halides electron density at the ring decreases due to electron withdrawing effect of halogen atom. 48. Answer (1)
RO R + H
+

R OH R

49. Answer (1) Phenoxide ion stabilized by resonance. 50. Answer (2) Correct reason :- Formation of stable intermediate benzyl carbocation. 51. Answer (3) Correct reason :- Intramolecular H-bonding 52. Answer (1)

OH H 53. Answer (2)

Benzene (aromatic)

Correct reason :- OH group of salicyladehyde is less reactive due to presence of intramolecular H-bonding. 54. Answer (3) Correct reason :- Rearrangement of carbocation form stable saytzeff product. 55. Answer (2) Intramolecular aldol reaction. 56. Answer (1) +I effect of CH3 group decrease dipole moment in ketone. 57. Answer (4) It forms 1 nitro 2 propanol. 58. Answer (1) Cl is good leaving group than NH2 group. 59. Answer (4) p-chloro benzoic is more acidic than p-fluoro benzoic acid due to more effective p-p bonding. 60. Answer (4) Guanidine is more basic due to stability of its conjugate pair. 61. Answer (2) In strongly acidic medium protonation of hydoxyl amine takes place.
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62. Answer (4) Chloro ethanoic acid has lowest value of pKa and stronger acid. 63. Answer (3) Cross Cannizzaro is redox reaction. 64. Answer (2) Cl is good leaving group. 65. Answer (4) +I effect of methyl group. 66. Answer (3) It has 3 H atom. 67. Answer (1) HCHO has 2H for hydride shift and benzaldehyde is resonance stabilised. 68. Answer (4) NaBH4 reduces only carbonyl group, not carbon-carbon multiple bond. 69. Answer (3) OH abstracts the hydrogen from CH3NO2. 70. Answer (4) 2, 2 dimethyl propanoic acid has no hydrogen does not gives HVZ reaction. 71. Answer (1) Zn-Hg/conc. HCl form cyclo alkene. 72. Answer (1) Umbrella effect. 73. Answer (3) Pyrrole is a weak base. It is aromatic because the non-bonding electrons on nitrogen are located in a p-orbital, where they contribute to aromatic sextet. 74. Answer (2) Due to hindrance. 75. Answer (1) +I effect of alkyl group increase electron density of N-atom. 76. Answer (4) Gabriel phthalimide is used for preparation of 1 amine in pure state. 77. Answer (2) The intermediate is stabilized by delocalization of negative charge on to the electronegative ion. 78. Answer (2)

NH C NH2
79. Answer (4)
H2O

NH2 C H2N NH2 (is stabilised by resonance)

NH2

In alkaline medium with ZnNaOH, nitrobenzene gives hydroazobenzene.


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80. Answer (1) CCl bond in chlorobenzene is resonance stabilised, it has partial double bond character. 81. Answer (2) Amides are less basic than primary amines because lone pair of electrons on nitrogen atom in amides is delocalised.
O R C NH2 O + R C = NH2

82. Answer (4) Carbylamine reaction is applicable to primary amines. 83. Answer (1)

+ N
similarly on the three rings.

84. Answer (1) In acidic medium, aniline is converted to anilinium ion which does not couple. 85. Answer (1) Carboxypeptidase is an exopeptidase as it breaks the peptide chain at terminal ends. Carboxy peptidase cleaves carboxy - terminal amino acids having aromatic or branched aliphatic side chains. 86. Answer (3) Nylon is a polyamide of hexamethylene diamine and adipic acid. 87. Answer (1) Bakelite becomes hard on heating, hardening is due to formation of extensive cross-links between different polymer chains to give a three dimensional network solid. 88. Answer (1) Carbocation formed from styrene (C 6H5 C H CH3 ) is more stable than that formed from propene. 89. Answer (4) Glycine does not contain a chiral centre. 90. Answer (3) Teflon is fully fluoroninated polymer. 91. Answer (4) Nylon is a monomer of hexamethylene diammine and adipic acid. 92. Answer (3) Polybutadiene is chain growth polymer. 93. Answer (3) Both glucose and fructose reduces Tollens reagent. 94. Answer (3) Cn(H2O)n General formula.
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95. Answer (1) On hydrolysis sucrose give unequal amount of glucose and fructose which changes sign of rotation. 96. Answer (2) Enzymes are generally made up of proteins. 97. Answer (2) Fructose is monosaccharide carbohydrate which do not undergo hydrolysis. 98. Answer (2) Existence of both cationic (NH3+) species and anionic species (COO). 99. Answer (2) Starch is polymer of glucose. 100. Answer (4) -D-glucose and -D-glucose are anomers.

Section - E : Matrix-Match Type


1. Answer - A(p, q, s), B(p, q, r, s), C(p, q, r, s), D(p, q, r, s)

OH
can react with Na, NaOH and NaNH2 but not with NaHCO3. While others react with Na, NaOH, NaNH2 and NaHCO3. 2. Answer - A(p, r, s), B(q, r), C(q, r), D(p, r, s) If two (+I) or two (I) effect groups are present on doubly bonded carbon atom then dipole moment (cis > trans), Melting point (trans > cis) and boiling point (cis > trans). If one (+I) and on (I) effect group is present on both boubly bonded carbon atom then dipole moment (trans > cis) and melting point (trans > cis) but boiling point (cis > trans). 3. Answer - A(q, r), B(p, q), C(r, q), D(q, r, s)

(A) Aromatic and resonance stabilised (4n + 2 = 6)

(B)

CH3 CH3 C C = C H +1 group

CH3

CH3 CH3 C = C C H

CH3 CH3

CH3 resonance

(C)

Aromatic and resonance stabilised (4n + 2 = 6)

CH2 N
(D)

O O Aromatic resonance and I effect of NO group. 2

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4. Answer - A(p, r), B(p, q), C(s), D(r) Friedel Crafts reaction
CH3

CH3Cl

anhyd. AlCl3

CH3

Reimer Tiemann reaction

OH
CHCl3, KOH

OH CHO

salicylaldehyde
Intermediate Carbene, an electrophile attack on electron rich ring Aldol condensation

O CH3 C H
OH

O CH2 C H carbanion

O CH3 C H

O CH2 C H

OH CH3 CH CH2 CHO

Acid catalysed hydration Carbocation is intermediate 5. Answer - A(r), B(p), C(q), D(q, s) Chlorination in presence of h is a free radical reaction. Bromination of alkene proceeds through cyclic transition state and undergoes anti addition. Hydration involves carbocationic mechanism, carbocation formed in this case will not undergo rearrangement. Elimination (E1) proceeds through carbocation, which has tendency of rearrangement. 6. Answer - A(q, r, s), B(q), C(p, s), D(s)

H
(A) Very acidic hydrogen so reacts with base it is allylic hydrogen which will be subslituted by Cl2/h. Presence of double bond will make it react with Br2 water. (B) Acidic hydrogen H CH2 O H Undergoes nitration with (HNO3 + H2SO4) as well as free radical addition with Cl2/h. free radical substitution with Cl2/h.

(C) (D)

7. Answer - A(s), B(q, r, s), C(p, s), D(q, r, s) (A) Cis elimination of meso compound produces trans isomer

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(B)

Elimination is possible from non-stereo centre. So, is a stereospecific reaction and a stereoselective reactions and undergoes antielimination.

H H H Br C C H Br H

H
(C)

H Carbocation would be formed, reactant is optically active product will show geometrical isomer hence the reaction is stereoselective.
Dehydration (elimination of H2O) proceeds through carbocationic intermediate which will undergo rearrangement. Elimination of HF from fluoroalkanes yields Hoffmann product Same as (1) Elimination of HCl proceeds through carbocation intermediate.

8. Answer - A(p, q, r), B(p, s), C(p, q, r), D(p, q, r) (A) (B) (C) (D)

9. Answer - A(p, q, s), B(p, r, s), C(p, q, s), D(p, r, s) Non terminal alkyne can form trans-alkene with Na/Liq.NH3 and does not react with ammonical AgNO3 while terminal alkynes do not form trans-alkene with Na/Liq.NH3 but reacts with ammonical AgNO3. 10. Answer - A(p, q, r, s), B(r), C(p, q, r), D(r) (A) (B) (C)
h CH4 + Cl2 CH3Cl + CH2Cl2 + CHCl3 + CCl4.

CHCl3 form carbene (:CCl2) with KOH. CH3Cl, CH2Cl2 and CHCl3 have dipole moment but CCl4 has zero dipole moment.

O
(D) reacts with Cl2 and NaOH to give haloform reaction and produce chloroform.

11. Answer - A(p, r, s), B(p, s), C(q), D(p) (A) (B) (C) (D) Dehydration in (A) will follow E1 mechanism, would be brought by H+, reaction will proceed through carbocation, which can undergo rearrangement. Same as (A) but carbocation will not undergo rearrangement, since it is benzylic carbon. Follows E2 mechanism. E1 mechanism follows carbocationic rearrangement.
H2O CH CH CHO CH3 C C H CH3 CH = CH OH tautomerisation 3 2 HBO

12. Answer - A(p, s), B(p, r), C(r), D(q) (A)

OH
(B) (C) (D)
OMDM

tautomeris ation CH3 C CH CH3 C CH3 CH3 C = CH2

Oxymercuration demercuration involves addition of H2O giving Markownikovs product. Oxo process.

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13. Answer - A(s), B(p), C(r), D(q)

Cl

%=

6 1 6 100 = 100 = 20.54% 6 1 + 3 + 4 3 .8 + 5 29.2

%=

Cl

5 100 = 17.12% 29.2

%=

Cl

7.6 100 = 26.0% 29.2

3 Cl % = 29.2 100 = 10.27%

14. Answer - A(p, r), B(p, r), C(q, s), D(s) (A) (B) (C) (D) Alc. KOH will bring elimination, reaction but the carbocation formed is stable so reaction will proceed through E1. Same. Sterically less hindered alkyl halide so will undergo E2 mechanism. E1CB.

15. Answer - A(p, r, s), B(p), C(q), D(r, s) Carbocation is stabilised by electron releasing group whereas it is destabilised by electron withdrawing group. 16. Answer - A(p, q, s), B(q), C(p, r, s), D(p, q, s)

OH
(A)

C CH3 H

CH CH3

CH = CH2

Elimination by E1 mechanism. (B) (C) (D) 2 alkyl halides are more prone to elimination in presence of sterically hindered base. Carbocation formed is aromatic so reaction proceeds through SN1. 3 alcohol will undergo E1 mechanism in presence of H+.

17. Answer - A(q, r), B(q, r), C(p), D(s) (A) (B) (C) (D) Friedel Craft alkylation and a electrophilic substitution. Friedel Craft acylation and a electrophilic substitution. Only possibility for chlorobenzene is SN with KOH, though that also is not feasible. Chlorination in presence of h is free radical reaction.

18. Answer - A(r), B(q), C(p), D(s) Tertiary alkyl halide gives E1 reaction while secondary alkyl halide gives E2 reaction. If two basic groups are present then elimination through E1CB.
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19. Answer - A(q), B(s), C(p), D(r)

Cl
(A) reacts with aqueous KOH gives SN2 reaction.

Cl
(B) reacts with alcoholic KOH gives E2 reaction and converted into alkene.

Cl
(C) reacts with H2O gives SN1 reaction and form tertiary alcohol.

OH
(D) reacts with H+ and on heating gives E1 reaction due to formation of tertiary carbocation.

20. Answer - A(r), B(p, r, s), C(q, r), D(p, r) (D) Reactant molecule undergoes anti-elimination but as the product cant exhibit stereoisomerism thats why reaction is not stereospecific.

21. Answer - A(p), B(s), C(q), D(q, r) (A) (B) (C) (D) Picric acid give CO2 with NaHCO3. Tertiary alcohol gives white turbidity within few seconds. 2 alcohol gives white turbidity after 8 10 minutes. Ethanol gives iodoform test. Ethanol give iodoform test and evolve H2 with sodium metal.

22. Answer - A(p, q, r), B(p, r), C(p, s), D(p, r) (A) (B) (C) (D) Stable carbocation intermediate due to rearrangement and stable Saytzeff product. 3 stable carbocation. E2 elimination. Unimolecular elimination.

23. Answer - A(q, s), B(p, r, s), C(q), D(p, r)

OCH3
(A)

OH 3HI OH + 3CH3I OH

OCH3 OCH3

So, product reacts with Na and CH3I is one of the product.

OCH3
(B)

I 6HI I + 3CH3I + 3H2O I

OCH3 OCH3

OPh
(C)

I OPh OPh 3HI I 3PhOH + I

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CH2OH
(D)

CH3 5HI CH I CH3 2 Alkyl halide

CHOH CH2OH

24. Answer - A(q), B(r), C(p, r), D(p) (A) (B) (C) In aldol condensation, carbanion is formed as an intermediate. In the formation of Grignard reagent, free redical is formed as an intermediate. In the Ist step free radical is formed as an intermediate while in IInd step carbocation is formed as an intermediate. In dehydration, carbocation is formed as an intermediate.

(D)

25. Answer - A(p, q), B(p, r), C(q, s), D(r, s)

O
(A)

H H

C=O

OH

O OH

O O
(B)

CH

OH

O CH

H
(C)

O C = O + CH3 C H
OH

CH3 C CH2 C H OH

O
(D)

O + CH3 C H H

C H

C=CCH

26. Answer - A(p, q, r, s), B(p, s), C(q, s), D(q, s) Phenol gives alkoxy benzene with Friedel Craft reaction, chloroform gives carbyl amine, phosgene gas and Reimer Tiemann reaction. 27. Answer - A(r), B(s), C(p), D(q) Based on data and acidic strength. 28. Answer - A(q, s, r), B(q, r, s), C(p, q, r, s), D(q, r, s) (A) (B) A gives ketone with H3O+ and HgSO4 and by HBO also undergo ozonolysis to form bicarbonyl compounds Alkene give ozonolysis and HBO reaction

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OH
(C)
PCC

OH + O3

Zn/H2O

OH O O

OH

HBO

OH OH

(D)

O3 Zn/H2O

29. Answer - A(q, r), B(p, r), C(s), D(p, s)

O CH3 C
, gives haloform test.

CHO gives positive Tollens test. OH and COOH, gives NaHCO3 test. 30. Answer - A(p, q, r, s), B(p, q, r, s), C(q, r), D(p, s) Acid with CaO/, acyl chloride with (CH3)2Cd and alkyl cyanide with Grignard salt give ketone. 31. Answer - A(r), B(p, q, r), C(r, s), D(r, s) Cannizzaro reaction is responded by aldehydes containing no H. Aldol condensation is responded by carbonyl compounds containing acidic hydrogen. Refomatsky reaction is responded by aldehydes only Tollens reagent can oxidise aldehydes only. 32. Answer - A(p, q, r, s), B(p, r), C(p, q, r, s), D(r) -keto acids can be decarboxylated by heating. 33. Answer - A(r), B(s), C(p), D(q) COCl COOH (A)
H3O
+

O COCl
(B)
NH3

C NH2

(Amide)
H2OH
(C)
CH3COOH

ester

COCl
(D)
RCOOH

Anhydride

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34. Answer - A(r, s), B(p, r), C(p, q), D(r, s) (A) (B) (C) (D) Hofmann bromamide Mannic condensation Aldol condensation Schemidt reaction

35. Answer - A(p, q, r, s), B(r, s), C(s), D(p, q, r, s) RMgX reacts with acidic hydrogen. 36. Answer - A(p, r), B(p, q), C(p, q, r), D(s) (A) (B) (C) 2 amine gives insoluble material with Hinsberg and yellow oily layer of p-nitrosoamine. 1 amine gives Hinsberg test and alcohol give red colour with Victor Meyer. 1 amine Hinsberg NO2 Red colour with Victor Meyer. (D) Only aldehyde give silver mirror with Tollens reagent

37. Answer - A(p, q), B(q), C(s), D(p, r, s) Amide can give amine with reduction as well as Br2/KOH 38. Answer - A(p, r), B(q, r), C(p, s), D(q, r) Only 3 N is present in benzene ring with sp2 hybridisation whereas 1 and 2 are non-benzenoid hetero aromatic and 4 N is aliphatic. 39. Answer - A(q), B(p, q, s), C(p, r), D(p, s)

Cl
(A)

Ag

N OH

N OH

N OH +

N O

NH2
(B)
HNO2 HCl

N2

ring expansion OH 2 alcohol gives blue colour with Victor Meyer

(C)

No ring expansion since Victor Meyer.

CH2 is stable than

CH2OH gives red colour with

O2N
(D)

NH2

O2N

OH

gives Victor Meyer test


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40. Answer - A(p, q, r, s), B(p, r, s), C(r), D(q, r, s) (A) Protein Polymer of amino acid formed by condensation of -amino acids and carboxylic acid having amide linkage.

O
(B) Nylon66 Condensation polymer having 2 monomeric units forming N C bond.

H
(C) (D) Buna N It is a copolymer of butadiene and vinyl cyanide. PHBV Poly hydroxy butyrate CO hydroxy valerate is a copolymer of 3-hydroxy butanoic acid and 3-hydroxy pentanoic acid in which the monomer are connected by ester linkages.

OH CH3 CH CH2 COOH + CH3 CH2 CH CH2 COOH OH


41. Answer - A(p), B(p), C(q, s), D(q, r) (A) (B) (C) (D) Buna-S is a co-polymer of butadiene and styrene. It is an addition polymer. Polythene is an additional polymer and is obtained by polymerizing ethylene. Nylon 6, 6 is obtained by condensation polymerization of hexamethylene diamine and adipic acid. Terylene is also called a polyester as it contain ester group. It is a condensation polymer.

PHBV

42. Answer - A(q, p), B(q), C(r, s), D(s) (A) (B) (C) (D) Ethylene glycol is a monomor used in formation of Terylene and Glyptal. Terephthalic acid is a monomer of Terylene. Formaldehyde is a monomer used in formation of Bakelite as well as malmac. Phenol is a monomer used in formation of Bakelite. Nylon 6 Formed by condensation of monomer. Glyptal It is a polyester formed by ethylene glycol and phthalic acid. Nylon 2, 6 It is a biodegradable, condensation polymer. Cellulose A polymer of -glucose units joined together by a glycosidic linkage is natural occur polymer and is biodegradable. Glucose is monosaccharides with 5 chiral carbon and D glucose differ in C1 configuration. Glucose and mannose has same molecular formula C6H12O6 but differ in configuration at 1-carbon only. Glucose and fructose are monosaccharides. Ribose and glucose are monosaccharides.

43. Answer - A(q), B(q), C(q, s), D(p, r, s) (A) (B) (C) (D)

44. Answer - A(p, q, s), B(p, r, s), C(s), D(s) (A) (B) (C) (D)

45. Answer - A(p, q, r, s), B(p, q, s), C(p, s), D(s) (A) (B) (C) (D) Glucose and mannose are monosaccharide both reducing sugar and are C2-epimers. Mannose and galactose are monosaccharides, reducing sugar. Glucose and fructose are monosaccharides and reducing sugar. Lactose and maltose are reducing sugar. (199)

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Organic Chemistry

46. Answer - A(p), B(p, q), C(r, s), D(p, q) (A) (B) (C) (D) Cellulose is polymer composed of D-glucose units which are joined by -glycosidic linkages. Proteins are nitrogeneous polymeric substance. Lipids are esters of long chain fatty acids and alcohols and richest source of energy stored in the living bodies. Nucleic acids are a group of high molecular mass biomolecules which are present in all living cells in format nucleoproteins. Nucleoproteins are made up of proteins and natural polymers.

47. Answer - A(q, r, s), B(p, r, s), C(q, r, s), D(q) Maltose, sucrose and lactose are disaccharides having glycosidic linkage and sucrose invert its configuration after hydrolysis. Fructose is reducing monosachharide sugar. 48. Answer - A(q, r), B(p, q), C(q, r), D(q, s) Glycine and alanine are amino acid form Zwitter ion. Protein has amide linkage form hydrogen bonds. DNA Nucleotide containing deoxy ribose sugar.

Section - F : Subjective Type

O
1. (i)
I Highly strained ring

The positive charge is resonance stabilised

O C

II

Greater charge separation in I assigns it a higher dipole moment than II.

(ii)

N H
In

N H
N H , no such resonance is possible. Hence, electron density is more over nitrogen atom.

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(iii)

is aromatic as it involves cyclic delocalization and follows Huckels (4n + 2) electron rule.

I
is not aromatic and hence is less stable.

II
O O CH2 OH H3C O CH3

2.

(i)

H3C

O
Both

and OH groups are in trans position and so no hydrogen bonding exists and can easily

tautomerise and it is more polar

O H3C

O CH3 H3C

O CH3 (II)

(I)

Here, intramolecular hydrogen bonding exists and is less polar. Thus compound (I) is more acidic than (II).

O
(ii)

is basic but

NH

is not because in the first case, the lone pair on nitrogen do not

participate in resonance with

since it will generate a double bond on bridge head position while

in the second case it does participate in resonance, decreasing its basicity.

O NH
+

O NH

(iii)

O is more acidic than OH

because its conjugate base is more stabilised.

OH

O O
3. (a)

O O O

O O

O O O

In compound (i) and (iii), there is plane of symmetry passing through the compounds (molecular plane). Therefore, they are optically inactive. Compound (ii) does not have plane of symmetry as the two phenyl rings are not in the same plane. One of the ring rotates about CC bond axis because of bulky substituents at ortho o positions of two adjacent phenyl rings and the two rings are perpendicular to each other. So (ii) is optically active. Compound (i) is optically active because there is no plane of symmetry which can cut the molecule into two equal halves. Compound (ii) also does not have plane of symmetry so, it is optically active. Compound (iii) is optically inactive because of the presence of centre of symmetry.

(b)

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4.

(i)

N OH
O

N O
H C O CH3 O O

(ii)

Ph

Ph C C = = = CH2

(iii)

O
(iv)

OH

O
N= =O

HO

N OH

O
(v)

HO

OH

OH

(vi)

O
H
(vii)

OH

OH
(viii)

CH3NO2
O

CH2 = =N O
OH CH3 CH3
OH CH3 H3C CH3

(ix)

H3C

C CH3
O

H3C

C CH3

CH3 CH3

(x)

H3C

H 3C

H 2C C=O C OH H 3C

(xi)

H 3C

O
(xii)

H3C H3C

CH3 CH3 has no -H atom; hence keto-enol tautomerism is not possible.

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OH Br
5. (i)

Br
(ii)

OH

Br Cl
(iii)

CH3 N H CH3

OEt
O
(iv)

OEt Cl

NO2
CH3 (CH2)2CH CH CH3
1, 2 hydride shift

NO2

6.

(i)

(CH2)2CH CH = = CH2
H

CH3 (CH2)2 C CH2 CH3


H

(ii)

CH = = CH2
H

CH CH3 ,

CH = = CH2

CH3
H

CH3 H CH3

7.

(i) Yes, each ring atom contributes a p-orbital perpendicular to the ring, and there are 10[4(2) + 2] electrons. Azulene is a non-benzoid aromatic compound. (ii) Addition of an electrophile to either starred carbon leads to an intermediate in which the seven membered ring is rendered aromatic

H E
+

E = = +

(iii) Attachment of a nucleophile to any one of the three starred carbons. Show here would render the five membered ring aromatic for e.g.

Nu

= = H Nu
(203)

H Nu

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8.

Na HC CH HC C Na + H2 HCl HC CH CH2 = CH2 CH3 CH2Cl

.......(1) .......(2)

Combine (1) and (2)

HC C Na + CH3CH2Cl

HC C CH2 CH3
i) Na ii) CH3CH2Cl

H3CH2CC CCH2CH3
Lindlar catalyst / H2 Na / liq NH3

H3C CH2 H C= =C

CH2 CH3 H

H H3CH2C C= =C

CH2CH3 H

(Z) -3-hexene
H3C
9.

(E) -3-hexene
CH2 CH Cl A CH Cl CH3

H2C

CH2

CH2

HCl (excess)

Mg/ether

OMgCl H3C C OC2H5 CH H3C CH2 MgCl


O

H3C CH
CH3C OC2H5

CH2 CH MgCl B

CH3

CH CH3

MgCl

H3C

O C CH CH2

MgCl CH
Br2

H3C

OMgCl

CH3

H3C H3C

OH

CH3

H3C

CH3

H3C

10.

H3C H3C Isobutene H3C H3C


Q

Br H3C

CH3 CH2Br

CH2

H CH3 Isobutane

Br2

No addition reaction

160 g Br2 is needed for 56 g of isobutene 20 g Br2 is needed for 56 20 = 7 g of isobutene 160 (204)

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Thus, Isobutene = 7 g, Isobutane = 3 g Now, 7 gm isobutene is converted into isobutane by reduction So, weight of isobutane =
58 7 = 7.25 g 56

Isobutane = 7.25 + 3 = 10.25 g

Now, C 4H10 + Br2 C 4H9Br + HBr [Isobutane reacts with Br2 to give monobromo product in light] So by reaction 58 g of C4H10 gives product = 137 g C4H9Br So (7.25 + 3) g of C4H10 gives product =
137 10.25 g 58

= 24.21 g C4H9Br
CH3

Br B = H3C Br

CH3 CH3

11. A = H3C

CH3

CH3 C = H 3C CH3

HO D = H3C

CH3 CH3 OH

CH3
E = CH3COOH

F = H3C

COOH

12. A = H3C

CH3 CH3

B = H3C CH3

CH3

OH C = H3C CH3 D = H3C CH3 CH3 O

CH3 E = HOOC

F = CH3COOH

O G = H3C CH3
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Br2

Organic Chemistry
base base

13. PhCH=CH2

Ph CH CH2 Br Br

Ph CH = = CHBr + Ph C = = CH2 E+Z Br

PhCCH

(ii)

RC=CH2 CH3

CH2I2 Zn / Cu

R CH3

H2 PtO2

RC(CH3)3

(iii)

(i) Base (i) Base HCCH (ii) CH I H3C C C H (ii) CH I H3C C C CH3
3 3

H2 Na, Liq. NH3

H 3C H C= =C

H CH3

KMnO4 OH

product

H 3C

(iv) 14. (i)

CH2 = = CH2

H3C

(i) BF3 THF (ii) Br2

Product

This mechanism combines electrophilic addition to the non-aromatic -bond, and electrophilic aromatic substitution. + H CH3 CH3

+ +

CH3
H
+

CH3 + H

(ii) This reaction involves a "tandem" electrophilic aromatic substitution.


+

NO2 H
+

NO2 H

NO2 H

H+

H
+

NO2 H

The last structure shown here is a 1, 4-cyclohexadiene derivative, which we know will be very easily oxidised +). One by HNO3 (which is a strong oxidising agent, as well as being strong acid and a source of NO2 +, possible mechanism for the necessary oxidation might involve extraction of the methine hydride by NO2 giving carbocation 'a', which could deprotonate to aromatize the second ring.
H NO2 H
+

NO2 H

NO2

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(iii) The first step is Markownikov protonation of the aromatic double bond to give the 2 carbocation. Then, either the Ph or CH3 migrates, followed by deprotonation.

CH3 H3C C CH = = CH2 Ph CH3


H OTs

CH3 Ph

H3C C CH CH3

H3C C CH CH3 Ph H+

CH3 H3C C CH CH3


+

Ph H+ CH3 H3C = = H3C C= =C Ph CH3

H3C C= =C Ph
15. CH3CH2CH2CH2Br
alc. KOH HBr

CH3
CH3CH2CH = CH2 (B)

(A)
Br2

CH3CH2HC = CH2 (B)

CH3CH2CH(Br)CH2Br (C)

CH 3CH 2CH(Br)CH 2Br (C)

NaNH2 2HBr

CH 3CH 2C CH (D)

CH3CH2C CH + Ag2O Tollen's But-1-yne reagent


NaNO2 EtOH

CH3CH2C CAg White ppt

16. (i)

nBuCl

nBu NO2
NaNO2

ClCH 2OCH2CH3 EtOH

(ii) ONO CH2OCH2CH3 + EtO CH2OCH2CH3 17. A = C6H5CH2CH2Br B = C6H5CH(Br)CH3 C = C6H5CH = CH2 D = C6H5CH2CH2OH D and E are isomeric alcohols E = C6H5CH(OH)CH3
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18. (i) In aqueous solution, the given alkyl bromide ionizes to give corresponding resonance stabilised tertiary benzylic carbocation and Br. This carbocation is attacked by ethanol follow by abstraction of proton by Br to produce corresponding ether and HBr. Due to HBr, the resultant solution becomes acidic. But the aryl bromide cannot ionise even in aqueous solution due to partial double character bond between carbon and bromine as a result of resonance. Therefore no reaction will take place. (ii) In the first aryl fluoride, attack of nucleophile (OH) is favoured by the presence of a strong electron withdrawing group (NO2) at para position. On the other hand in second aryl fluoride, attack of nucleophile (OH) is opposed by the presence of an electron donating methyl group at para position.

19.

HBr

Br

HO CH2 CH2CH2CH2 CH2 Br

HBr

Br CH2CH2CH2CH2CH2 Br

O H

CH3
20. (i)

CH3
HBr

CH3 CH CH CH3 OH CH3 CH3 CH2 C CH3 Br

CH3 CH CH CH3 OH 2 CH3

H2O

Br

CH3 CH2 C CH3

CH3 + CH3CH C CH3 H

(ii) CH3 CH2 CH OH


CH3

HBr

CH3 CH2 CH OH2 CH3

H2O

CH3 CH2 CH CH3

Br

CH3 CH2 CH Br CH3

21. (i)

CH2 CH3

NBS in CCl4

CH CH3 Br

alc. KOH

CH = CH2

(ii) CH3CH2CH = CH2

HBr in H2O2

CH3CH2CH2CH2 Br HBr

NH3

CH3CH2CH2CH2 NH2

CH2
(iii) HOCH2CH2CH = CH2
H
+

CH2 CH2 CH2


H
+

(iv)

Cl2/h

Cl
CH3O Cl

OCH3

(v) CH3CH2CH = CH2

NBS in CCl 4

CH3CHCH = CH2 Br

alc. KOH

CH2 = CH CH = CH2

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22. (i) Decreases (ii) Decreases (iii) Increases

CH3
23.

COO CH CH3 OH (A)

NaOH,

COONa + CH3 CH CH3 OH (A) OH

COOH OH OH CH3 CH CH3


(In NaOH) NaOH

(B) CH3COONa + CH3I3


Yellow ppt.

24. (i)

MeO + H2 C CH CH2 Cl O MeO CH2 CH CH2 + Cl O


14

14

SN2

CH3O CH2 CH CH2 Cl O

14

(ii) Place an O atom between the C's bonded to I's (a) (CH3)3COCH3CH2CH3 (b) cyclohexyl and methyl iodides and (c) The presence of two I's in the same product indicates a cyclic ether, i.e. tetrahydrophyran (iii) In addition to the amount of electron density on the nucleophilic site, steric affects also influence basicities. The greater the steric hinderance encountered in the formation of coordinate bonds, the weaker is the Lewis basicity. In tetrahydrofuran, the R group (the sides of the ring) are tied back leaving a very exposed O atom free to serve as a basic site. The 2 R group in di-isopropyl ether furnish more steric hinderance than do the 1 ethyl groups in ethyl ether. The order of decreasing Lewis basicity is thus tetrahydrofuran > diethyl ether > di-i-propyl ether.

25. [X] is

CH2 CH2 CH2 C CH OH


Pent-4-yn-1-ol

CH2 CH2 CH2 C CH + 2CH3MgBr 2CH4 OH [X]

Q 84 g [X] gives 222.4 lt. CH4

0.42 g [X] will give

2 22.4 0.42 = 224 ml CH4 84

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HO
26.

HO C6H3 CH2 CH = = CH2


OH

C6H3CH = = CH CH3 H3CO (C) C10H12O2

H3CO (A) C10H12O2


CH3O C6H3 CH2 CH = = CH2 CH3O (B) C11H14O2
OH OH
27. (A)

OH

H3CO C6H3CH = = CH CH3 H3CO (D) C11H14O2

OH OH
(B)

CH(OH)CH2NHCH3

C CH2Cl O

OH OH
(C)

C CH2NHCH3 O
H 3C OH HgOAc H H 3C B= OH

28. (i) (ii)

A=

A = CH3CH2CH2OH B = CH3OH

OH
(iii) A = PhMgBr
CH3

B = Ph

(iv)

H 3C C OH + C 2H 5OH CH3

(v)

RCO2Et + MgBr R

MgBr

followed by H3O
+

R OH

R
H2/Pd

H2O

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(vi) (vii)

No reaction 6 HCOOH

OH
29. (i)

HO

H + H3O

HO O
H
+

ring expansion OH

OH
(ii)

+ OH H O H

OH

O
+ OH2 H2O H
+

H3C

OH

H3C

CH3

(iii)

CH3

Me
(iv) Me

Ph Ph
H
+

Me Me OH

Ph Ph

Me

Ph Ph

OH

OH

OH

Me

Me Ph C O Me Ph
H
+

Me Ph Ph H O Me

(v)

OH OH

H OH OH2

H2O

+ OH

O H

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Organic Chemistry

O
30. (i)

O C CH2 CH2 C O CH2 O CH2 CH2 CH3 H2O

CH3CCH2CH2CCH3 O O

dil OH 100C

H2C

C H3C

O C CH C CH2 CH2 HO , H2O

O C CH2 C CH2 CH2 CH3

CH3

(ii)

CH3CCH2CH2CH2CH2CCH3 O O

dil OH

CH2 H3C C CH O H3C C O

CH2 CH2

O H3C C H3C H2O H3CCO H3C OH H2O(OH ) CH3CO H3C

(iii)

H3CCCH2CH2CH2CH2CH2CCH3 O O

dil OH

CH2 H3C C CH O H3C C O H2C CH2 CH2

O H3C C H3C

O H3C C H2O H3C OH H2O (OH )

O H3C C H3C O

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O O

(iv)

CH3CCH2CCH3 O O

dil OH

CH3CCHCCH3 O O O

CH3CCH2CCH3

O H3C C H3C O C CH2 C O O CH C CH2 CH3

O O H3C C CH H3C C O C CH2 C=O CH2 CH3 dil. OH

O H3C C CH H3C C O H3C C

CH3 CH2 C=O

O O CH3 H3C C HO C CH H3C C CH2 OH CH2 C O O O H3C C C=C H3C C CH C CH3


Tautomerize

H3C C C=C H3C C CH

CH3 CH C OH

CH

O
31.

H5C6 CH3 NH2OH, HCl H3C N


Anti

OH +

H5C6 N H3C OH
syn

(A)

(B)

(oxime)

(C)

Ph N H3C OH and

Ph N CH3 OH H3C D KOH NH2 CH3 COOK + (F) NH2 CH3COCl N H O , CH3 E KOH (E) Ph

O + H3C NH Ph (D)

NH

CH3CN + PhCOOH
White solid

(F)

(G)

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32. (i)

O
O CH3 O
(ii)
Br2 NaOH H
+

O CH3 COONa + Br Br Br

CH3

O CH3 COOH
CO2

O CH3 H

Easy decarboxylation

(iii)
COOH

SOCl2 COCl

AlCl3

Zn-Hg HCl Conc. HCl

O (A) (B) (C)

O
OH OH
+

O
1 eq. H

OH O CH O (A) (B)
NaBH4 CH3OH H3O
+

OH O CH O (C)

(iv)

CHO

CHO

O O
33.

PhMgBr

CH2 Ph C O ..

C=O CH2

O H2O HOH Ph C CH2 C OH CH2

Ph O

34. (i) Number of products are three

(ii) CH3 C = CH2 | CH3

H/HOCl Cl + + OH

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..
+ CH3 C CH2 | CH3 Cl +
OH

OH | CH3 C CH2 | | CH3 Cl

(214)

Organic Chemistry

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35. (i)

A =

CO

CH3

B =

CH2CH3

(ii)

C =

OH

D =
O NH C2H5

O
(iii)

E =

S O O

F =

S O

C2H5

G =

S O

H =

SO3H

(iv)

I = (C2H5)2NH2 J = (CH3NH)2C
S

N(CH3)2
36. (i)

CH3OH + N(CH3)2

(ii) (iii) (iv)

CH2 = CH CH3 +
(major)

CH 2

CH2 + N(CH3)2CH2CH2CH3
CH2 + N(CH3)3

CH3 CH3
37. X = CH3

CH3
Y = CH3

CH NH2 (optically active)

CH

C OH

CH2CH3

(Optically inactive)

CH2OH
38. CH2

CH2Cl CH2 CH2 CH2Cl (B)

CH2CN CH2 CH2CN (C)

CH2CH2NH2 NH CH2CH2NH2 (D) (E)


O
C Cl C

CH2OH (A)

NO2
39. (i)
Conc. HNO3 Conc. H2SO4 (1) Sn/HCl (2) OH

NH2

NH

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CH3
(ii)

CH3
Moist Ag2O AgI

NH

excess CH3I

H2O

N(CH3)2

CH3

CH3

H O
40. (i)
H
+

H HO N(CH3)2
H+

OH

OH
(CH3)2NH

HO

N(CH3)2
H+

HO

N(CH3)2

H2O

N(CH3)2
H BH2CN BH2CN

N(CH3)2

(ii)

H2 / Pt

H2 / Pt

CN

1 equivalent

CH = NH

1 equivalent

CH2NH2

O H

CH2 NH2

H2O

IMPE

N H
H
+

N H H H
H2/P2

N O H OH H

N H

O H

CH2 NH2

N H

41. (i) Buna-S CH2 CH = CH CH2 CH CH2 , monomers styrene, 1, 3-butadiene

(ii) PHBV O CH CH2 C O , R = CH3, C2H5, monomers 3-Hydroxy butanoic acid


R O
n

3-Hydroxy pentanoic acid


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H
O

N
(CH2)5 NH
n

O
caprolactum (monomers)

(iii) Nylon 6

Cl
(iv) Neoprene CH2 C = CH CH2 , monomers = chloroprene
n

(v) Glyptal OCH2 CH2OOC

COO
n

(i) Buna-S Polymer of butadiene Styrene Chain growth. (ii) PHBV (Poly -hydroxy butyrate Co--hydroxy valerate) Monomen 3 hydroxy butanoic acid and 3-hydroxy pentanoic, step growth polymer. (iii) Nylon 6 Caprolactum step growth. (iv) Neoprene 2 chloro 1-3 butadiene, chain growth polymer. (v) Glyptal Phthalic acid and ethylne glycol step growth polymer. 42. Let the fraction of glucose present as the anomer [() = +112.2] is a, the fraction present as the anomer [() = + 18.7] is b and the rotation of the mixture is + 52.6, We have a(+ 112.2) + b(+ 18.7) = + 52.6 There is very little of the open-chain form present, so the fraction present as the anomer (a) plus the fraction present as the anomer(b) should account for all the glucose. a + b = 1 or b = 1 a Substituting (1 a) for b in the first equal, we have a(112.2) + (1 a)(18.7) = 52.6 Solving this equation for a we have a = 0.36 or 36%. Thus b must be (1 0.36) = 0.64 or 64% anomer = 36% anomer = 64% The anomeric hydroxyl group is axial in anomer and equitorial in the anomer. So it is obivious that more stable anomer predominates.
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43. (i)

P = COOH

(ii)

Q = COOH

(iii)

R = COOH

(CHOH)4 CH2OH gluconic acid

(CHOH)4 COOH gluconic acid

CHOH (CHOH)3

+ rearrangement + Ag (silver mirror)

CH2OH gluconic acid


44. The isoelectric point (pI) is the pH at which the amino acid exists only as a dipolar ion with net charge zero. At isoelectric point, for a neutral amino acid, pI =

(pK a + pK a )
1 2

2 The dissociation of cationic form of valine can be represented as


CO2H CHNH3 CH(CH3)2
Net charge (+) (pKa1) OH H+

CO2

CHNH3 CH(CH3)2
(0)

(pKa2) OH H+

CO2

CHNH2 CH(CH3)2
(1)

The species with zero net charge exists between species with (+ 1) and (1) net charges.

pI =

(pK a + pK a )
1 2

9.69 + 2.31 =6 2

When the pH of the solution equals to pI, the structure of valine is CO2

CHNH3 CH(CH3)2
When the pH of the solution is two, the structure of valine is CO2H

CHNH3 CH(CH3)2
When the pH of the solution is 12, the structure of valine is CO2

CHNH3 CH(CH3)2
45. -glucopyranose is the cis-1, 2-diol and the -anomer is the trans-1, 2-diol. Since the former can form a cyclic ester with periodic acid and the latter cannot, the former is oxidised more rapidly than the latter. 46. Only C-1 and C-2 are involved in osazone formation. Hence, aldohexoses and ketohexoses, which have the same configuration at C-3, C-4 and C-5 give the same osazone. CHO CHO CH2OH

H HO H H

OH H OH OH CH2OH

HO HO H H

H H OH OH CH2OH HO H H

CO H OH OH CH2OH D-fructose
(218)

D-glucose

D-mannose

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47.

OMe H CH2OMe H MeO H O H CH2OMe MeO H H

MeO

H CH2OMe

MeO

H MeO

OH H H 2, 3, 4, 6-tetra-o-methyl-D-glucose + HO H CH2OMe OMe H MeO OMe H

OMe O

48. A H2C = CH2 B HO CH2 CH2 OH C HOOC

OH H H 2, 3, 4, 6-tri-o-methyl-D-glucose

O O O O O O OH

49. (a) (i) Sucrose has no free anomeric OH. (ii) D-glucose and D-fructose are linked by their anomeric OHs, the of one with OH of ether (hydrolysis by emulsion). (iii) The glucose unit is a pyranoside because the C5 OH is unmethylated. (b) Fructose ring size and glycosidic linkage (actual linkage is to glucose and to fructose). (c) The sweeter form is fructopyranose. The high temperature causes a shift in the pyranose equilibrium towards the less sweet furanose. 50. (A) Contains 92.3% C & 7.3% H. Thus it is CH CH (B) Contains 90% C & 10% H, thus it is CH3 C CH CH3 furanose

C CH CH CH CH CH
Red hot tube

CH3
CH3COCl AlCl3

CH3
I2/NaOH

CH3 + CHI3 COOH (E)

(C)

CH3
SOCl2

CH3
NH3

CH3
Br2

COCH3 (D) CH3

NaOH

COOH

COCl

CONH2 (F)
(219)

NH2 (G)

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51. Since the last compound is p-dibromobenzene, hence the starting compound must be o-toluedine, because it gives carbylamine reaction and can be diazotised

CH3 NH2 (A)


(CH3CO)2O

CH3 NHCOCH3 (B)


Br2 Fe Powder

CH3 NHCOCH3 Br (C)


H2O/H+

CH3 NH2 Br (D)


NaNO2 / HCl 05C

Br

(i) Oxidation (ii) NaOH/CaO

CH3 Br Br
CuBr HBr

CH3 N2 Cl Br
+

Br
p-dibromobenzene

(E)

52. Since compound (A) on heating with KOH eliminates HBr, hence Br atom is in side chain not in the ring. Thus (A) is N-bromobenzamide which gives unstable species (B) which changes into phenyl isocyanate (C). The isocyanate on heating with KOH gives aniline, which is diazotised and the product couples with B-naphthol to give orange red dye.

O CNHBr
KOH , KBr, H2O

O .. CN
Rearrangement

N=C=O

2KOH / Aniline

NH2

..

Phenyl isocyanate K2CO3

(A)

(B)

(C)

(D)
NaNO2 + HCl 0 5C

N=N OH
(Orange red dye)

OH

N2Cl

NaOH Coupling reaction

(E)

53. The aromatic amine (A) if considered as 2-methyl pyridine, then all foregoing reactions can be explained as
(i) CH3I

Ni / H2

N (A)

CH3

N H (B)

CH3

(ii) Ag2O moist

N CH3

CH3 CH3{OH

under reduced pressure

+ N CH3 (D) CH3 CH3 N CH3 (E) CH2 CH3

(C)
Quarternary ammonium hydroxide

(i) CH3I

(i) CH3I

N CH3 (D)

CH3 CH3

(ii) Ag2O, moist (iii)

N CH3 (E) (F)

CH2 CH3

(ii) Ag2O, moist (iii)

CH2 (G)

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54. Ozonolysis of A gives 4-ethoxy-3-hydroxy benzaldehyde (C).

CHO A
(i) O3 (ii) Zn/H2O

+ CH3 CH = O OH OC2H5

The A is obtained by heating, A with strong alkali i.e. the isomerisation of A into A. This isomerisation involves the migration of double bond from terminal position to adjacent carbon. This isomerisation suggests the IInd part of the ozonolysis product is acetaldehyde. From these two ozonolysis product, the structure of A can be formulated as

OC2H5 OH

strong alkali CH2CH = CH2 (A)

OC2H5 OH

CH = CH CH3 (A)

By the structure (A) other structures can be formulated by the following reaction.

OC2H 5 OH

(CH 3)2 SO4 NaOH

OC2H 5 OCH 3

CH 2CH=CH 2 (A) reflux Strong alkali OC2H 5 OH HI OH OH + C2H 5I CH 2CH=CH 2

CH 2CH=CH 2 (B) Strong alkali OC2H 5 OCH 3

CH=CHCH3 (A') (I) O3 (II) Zn/ H O 2 OC2H5 OH

CH=CHCH3 (B') (I) O3 (II) Zn/ H O 2 OC2H 5 OCH 3

CHO (C)

CHO (D)

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55.

Since (A) has degree of unsaturation 2. The ozonolysis of A gives (B) having same number of carbon atom. Thus (A) must have one ring and one double bond. The only structure of A i.e. cyclopropene is possible containing one double bond and one ring. On the basis of (A) other structure may be formulated as

CH 2 CH = CH (A) CH 2

(I) O 3 (II) Zn / H 2O

CHO CH 2 CHO (B) CH 2Cl PCl 5 CH 2

Na / C2H 5OH

CH 2OH

CH 2Cl CH 2OH (C) C is 1-alcohol hence gives red colour with leric ammonium nitrate & diacetyl derivative CH 2 CH 2 NH 2 CH 2 CH 2 CH 2 NH 2 (E) CH 2 CN Reduction LiAlH4 CH 2 CH 2 CN (D) KCN

2HCl

CH 2 CH 2 NH 2 HCl CH 2 CH 2 CH 2 NH 2 HCl (E) N CH 3 I Quaternary salt CH 3I

H 2SO4 N | H (F) Pd/C

N (G) Pyridine

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(222)