Organic: Alcohol, Ether, Phenol (MOMENTUM)

ITQ(1-29) , SCTQ(30-41), MCTQ(42-72) , SCTQ(73-143), ITQ(144,147), (145-146 Written)

Q 1. No of Pentyl alcohols producing blue colouriation in the victor Meyer’s Test is

Q 2. Number of reagents which give cis diol with alkene are

(1) KMnO4 / OH- / H2O (2) OsO4
(3) I2 / CH3COOAg (wet) (4) I2 / CH3COOAg (dry)
(5) ArCOOOH / H3O
Q 3. Alcoholic group at position __________ reacts fastest with Lucas reagent.
O OH
HO
2 OH
1 3 4 5
OH
Q 4. OH OH H+
(P)
CH3CH3

In the product P the carbonyl group carries how many  hydrogen?

Q 5. 0.037 g of an alcohol R-OH was added to CH3 MgBr and the gas evolved measured 11.2 ml of STP. The number of
carbons in the alcohol
Q 6. Find out the number of possible E1 products from the following reaction (Excluding stereoisomers)
Br
CH3OH

Q 7. How many of the following substances are less acidic than ethyl alcohol.
Water, acetylene, Carbonic acid, methanol, isopropyl alcohol, phenol, tert-butyl alcohol, n-propyl alcohol.
Q 8. 30 g of CH3MgBr Reacts with excess of CH3CH2CH2OH forming x g of a gas x is (nearest integer)
Q 9. Find out number of alcohols that can give positive iodoform test.
OH OH
OH
CH CH 3
OH
(c) (d)
(a) (b)
OH HO

CH 3 CH 2 OH CH 2 OH

(e) (f) (g)

(h)
Q 10. How many following compounds are belongs to dihydric alcohol from the following?
Glycerol, Carbinol, Glycol, Catechol, Quinol, Cresol, Resorcinol, Sec-Butyl alcohol, Picric acid, Carbolic acid,
Pyrogallol, Hydroxy quinol.
Q 11. How many moles of periodic acid are consumed in reaction with the following organic compound?
OH O OH

OH O
Q 12. A molecular having formula C7H8O can show maximum number of aromatic isomers…..
Q 13. The total number of alkenes possible by dehydrohalogination of -3-bromo-3-cyclopentylhexane using alcoholic KOH.

Q 14. How many of the following get oxidized by Br2 / KOH into carboxylic acid?

CH CH3
(A) CH3  CH2  OH (B)
OH

OH
(C) CH2OH (D) CH3

O O
 (E) (F)

Q 15. How many options are correct about reaction I and reaction II
Reaction-I
The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(I) Alkyl chlorides are immscible with SOCl2
(II) The other products of the reaction are gaseous and escape out
(III) Alcohol and SOCl2 are soluble in water
(IV) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite

Reaction-II
Lucas test is used to make distinction between 1°, 2° and 3° alcohols
anhydrous ZnCl2
ROH + HCl RCl + H 2O
conc. White turbidity
This shows that
(I) ROH behaves as a base
(II) Greater the value of pKa (alcohol), greater the reactivity with conc. HCl and thus sooner the formation of
turbidity
(III) Alcohol reacts fastest with sodium metal, will give turbidity at fastest rate
(IV) Alcohol which gives Red colour during victor mayor test, will give turbidity at slower rate than those giving
Blue or White colour during victor mayor test
Q 16. How many Reagents are not oxidizing reagents from the following?
K2Cr2O7, NaBH4, Na/C2H5OH, Cu, KMnO4, CrO3, LiAIH4, Aluminimumisopropoxide, Na2Cr2O7/H2SO4, Sn/HCI,
MnO2, SeO2, H2/Ni, BH3/THF, HI/RedP HIO4.
Q 17. O
CH 3 C CH 2 (I) CH3MgBr H+
(P) (Q)
(II) H2O/H+ 
CH 3
The product “Q” carries how many hyper conjugating structures?

Q 18. The cleavage of ethers to give the original alkyl halides and the alcohol is carried out by heating the ether with a halogen
acid. Usually HI at 373 K is used, but some ethers can be cleaved even by HBr or HCI. Depending upon the nature
of the alkyl/aryl groups around the oxygen atom & the polarity of the solvent in which HI is dissolved, the reaction
may follow either SN2 or SN1 mechanism.

1. Which of the following ethers is cleaved even by hydrogen chloride at room temperature?
(A) C6H5O-CH2CH3 (B) CH3CH2-O-CH2CH3
(C) (CH3)3COCH2CH3 (D) (CH3)3COC(CH3)3

2. Tert-butyl methyl ether on heating with 1 mole of HI in anhydrous ether gives

(A) CH3I + (CH3)3COH (B) CH3OH + (CH3)3 CI
(C) CH3I + (CH3)3CI (D) CH3I + (CH3)2C = CH2
Q 19. Grignard additions to carbonyl compounds are especially useful because they can be used to prepare, secondary or
tertiary alcohols. When a Grignard reagent adds to the carbonyl group of an ester, the initial product is unstable and loses
a magnesium alkoxide to form a ketone. Ketone is more reactive towards nucleophile, compaired with ester and finally a
tertiary alcohol will formed if G.R. is not used in controlled manner.

1. In the following reaction sequence, the structure of A and B are respectively:

(A) (B)

(C) (D)

2. The major product in the following reaction is

O OH

(A) (B)

(C) COOH (D)

Q 20. A reaction characterstic of vicinal diols is their oxidative cleavage on treatment with periodicacid HIO  . The carbon-
4
carbon bond of the vicinal diol unit is broken and two carbonyl group result. Periodic acid is reduced to iodic acid
HIo3 
1 1
R R R R
1
R C C R + HIO 4
1
C O+ 1 C O + HIO3 + H2O
OH OH R R
Cyclic diols reacts to give dicorbonyl compounds. The reactions are faster when the hydroxyl groups are cis. than when
they are trans, but both stereoisomers are oxidized by periodic acid. Periodic acid cleacage of vicinal diols is often
used for analytic purposes as an aid in structure determination. By identifying the carbonyl compounds produced,
the constitution of the diol may be deduce

1. Which of the following compound/s are obtained when the following compound I oxidized by HIO 4?
CH3
CH C CH3
OH OH
O O
C OH
CH3 C CH3
(A) (B)
O O
C CH3
CH3 C H
(C) (D)
 OH HIO4
X

2. OH
The compound X in the above reaction is
O

(A) O (B) CHO  CH2  CH2  CH2  CHO

(C) both of these (D) none of these

3. When Arabinose is oxidized by HIO4, then formaldelyde and formic acid are obtained. Number of molecules of
formic acid and formaldelyde obtained respectively are
(A) 3, 2 (B) 4, 1
(C) 1, 4 (D) 2, 3
Q 21. When pinacols [Mostly ditertiary alcohols] are treated with mineral acids like H2SO4, HNO3. They rearranges to form
ketones are called “Pinacolones” with the elimination of H2O. The reaction mechanism of pincol-pinacolone rearrangement
through carbocation intermediate. This carbocation is stabilized by electron releasing groups.
[Me=Methyl group CH3]
CH 3 CH 3 H+ CH 3 CH3
H 3C C C CH 3 H3C C C Me
S tep ( 1)
: OH : +OH :
.. OH 2 OH
.. ..
[pinacol] Slow step (2)
Rate determing step.

CH 3 CH 3
H 3C C C CH 3
+
: OH
..
CH 3 group shif t step (3)

+ CH 3 ..
O H :OH CH 3 CH 3
CH 3
H3C C C CH 3 H3C C C CH 3 H3C C C CH 3
+ +
CH 3 CH 3 : OH
..
- H+/step 4

CH 3 O+
H3C C C CH 3 [pinacolone]
CH 3

1. Identify the correct product (X) from the following reaction?

H2 S O4
X
OH OH

(A) (B)
OH O

(C) (D)

O O

2. Which of the following one is incorrect statement regarding pinacol-pinacolone rearrangement?

(A) Pinacols obtained by reduction of carbonyl compounds with Mg amalgam followed by acid hydrolysis.
(B) Tertiary carboncations are stabilized by Electron releasing groups in pinacol-pinacolone rearrangement.
(C) The migrating group should be cis to the leaving group.
(D) All are incorrect statements.
Q 22. Na/E ther
(A) C 3H4 (D) (C 3H3Na)
(i) + B
Dil. H 2 S O 4 + Hg+2 (+)
(ii) H3 O

(B) C 3H6O E (C 6H10O)

(i) Mg/Ether
H2 + P d + BaS O4 + quinoline
(ii) H 2O
F(C 6H12O)
(C)

1. The compound (B) is

H O
(A) (B)
Me O Me Me
OH OH
(C) (D)
Me
Me
2. Which of the following statements is correct for the formation of (‘C’) from (‘B’)?
(A) ‘C’ is 1, 2 diol and its formation involves a radical intermediate
(B) ‘C’ is 1, 2 diol and its formation involves a radical anion intermediate.
(C) ‘C’ is 1, 2 diol and its formation involves a carbocation intermediate
(D) ‘C’ is 1, 2 diol and its formation involves a carbonion intermediate

3. Which statement is correct for the formation of (B) from (A)?

(+)
(A) The formation of ‘B’ involves CH2 (allyl carbocation) intermediate

(+)
(B) The formation of (B) involves carbocation as kinetically controlled product.
Me CH2

(C) The formation of (B) involves . (alllyl radical) intermediate

CH2

.
(D) The formation of (B) involves Me CH2 radical as kinetically controlled product.
Q 23. Although epoxides do not contain a good leaving group, they contain a strained three-membered ring with polar bonds. Nucleophilic attack opens the strained
three-membered ring, making it favourable process even with the poor leaving group.

O O leaving group
 
C C C C
Nu

Nu
This reaction occurs readily with strong nucleophile, and with acids like HZ, where Z is nucleophilic atom.
H OH
Reaction with O H H
strong H CN/H2O
nucleophile H
H H CN H Nucleophile
opens the
3-membered ring
H OH
O H H
Reaction with H HCl
HZ H
H H Cl H

1. Find out correct product of the reaction:

CH3

O 1.C2H5O
2.H2O
CH3
OH CH3
(A) (B) OH
OC2H5
CH3 OC 2H5
OH
(C) (D) CH3

OC2H5 OC 2H5
H3C O
HCl
2. ? OH
H3C
What would be the major product of reaction? Cl
Cl
(A) (B)
OH
OH
OH Cl
(C) (D)

Cl HO
Ph O
3. 1. H
?
CH HC CH2 2. CH3OH
H3C
Find out major product of reaction:
Ph
Ph OH
(A) (B)
CH2 CH2 OH
H3C OCH CH CH CH2
3
H3C
OH OCH 3
Ph
(C) (D) None of these
CH CH CH2
H3C
OCH3
Q 24. An organic compound (X) on treatment with CHCl3 and KOH gives (Y) and (Z) both of which in turn gives the same
compound (T) when distilled with Zn.
Oxidation of (T) yields (S) of formula C7H6O2 . The sodium salt of (S) with sodalime gives (P) which can also be obtained
by distilling (X) is:

1. Themolecular weight of compound (X) is:

(A) 122 (B) 94
(C) 106 (D) 78

2. TheCompound (T) is:

OH
(A) (B)

CHO COOH

(C) (D)

3. Compound (Y) and (Z) could be:

OH OH
OH OH
CHO
(A) CHO (B)
and
and
CHO
CHO
OH CHO COOH OH
CHO
(C) (D)
and and

Q 25. Compound A  C6H14O gives H2 on reaction with Na metal, it does not reacts with NaOH and gives Lucas test in a few
seconds. When A is treated with PBr3, we get compound B  C6 H13 Br  , which on heating with alc KOH yields C,( C6H12
)and D  C6H12  .Compound C is major product while compound D is a minor product . When C is treated with O 3 followed
by hydrolysis only single ketone is obtained this ketone can also be obtained by hydration of propyne in presence of dii
H2SO4 / HgSO4

1. Compound A would be
(A) 10 Alcohol (B) 20 Alcohol
(C) 30 Alcohol (D) Ether

2. The structure B would be

(A) (B)
Br
Br

(C) (D)
Br Br
Q 26.
( i) C 2H 5MgB r
O Y+Z
X ( ii) H 3O +

X Reacts with mole of C2H5MgBr to form to different compound Y & Z.

1. X – can undergo
(A) 1, 2 - addition (B) 1, 4 - addition
(C) nucleophillic addition reaction (D) Nucleophillic Substitution

2. One of the compound (say y) is

 (A) C2 H5 (B)

HO OH
(C) (D) None of these

OH
Q 27. In the following reaction sequence products I, J & L are formed. K represents a reagent.
Me H2
Cl L
P d/B aS O4
1. Mg/ ether O
Hex  3  ynal 
1.NaBH4
 I 
2.CO2
 J 
K
 quinoline
2.PBr3 3. H O 3

1. The structure of the product I is

(A) Me Br (B) Br
Me Br
(C) Br (D)
Me

2. The structure of product L is

Me CHO
(A) (B) Me CHO
CHO
(C) (D) Me CHO
Me

3. The structures of compounds J and K, respectively, are

OH and SO2CI2
(A) Me COOH and SOCI
2 (B)
O
Me
(C) and SOCI 2 (D) Me COOH and CH 3SO2CI 2
COOH
Q 28. A volatile organic compound (X) on reaction with HI gives two products (Y) and (Z). Z gives red colour inVictor Meyer test
but when (Z) is heated with conc.H2SO4 followed by hydrolysis gives (P), whichImmediately reacts with anhydrous
ZnCl2  HCl. (Y) on treatment with C2H5OH  KOH followed O3 / Me2S gives Q. (Q) can give halo form test. (Q) When
heated with NaOH gives (R). (R) Also giveshalo form test and can decolorize Br2 water.

1. Compound (X) is

(A) (B)

(C) (D)

2. Compound (Y) is

(A) (B)

(C) (D)

3. Compound (R) is

(A) (B)

(C) (D)
Q 29. The cleavage of ethers to give the original alkyl halide and the alcohol is carried out by heating the ether with a halogen
acid. Usually HI of 373 K is used, but some ethers can be cleaved even by HBr or HCI. Depending upon the nature of the
alkyl/aryl groups around the oxygen atom and the polarity of the solvent in which HI is dissolved, the reaction may follow
either SN2 of SN1 mechanism.

1. Which of the following ethers is cleaved even by HCI at room temperature?

(A) C6H5OCH2CH3 (B) CH3CH2OCH2CH3
(C) (CH3)3C-O-CH2CH3 (D) (CH3)3COC(CH3)3

2. Tert –butyl methyl ether on heating with one mole HI in anhydrous ether gives
(A) CH3I + (CH3)3COH (B) CH3OH + (CH3)3 CI
(C) CH3I + (CH3)3 CI (D) CH3I + (CH3)2C=CH2

3. The major products formed when the following ether is heated with conc. HI are CH 3 CH2 CH2O C(CH3)2 CH2 CH3
(A) CH3 CH2CH2 I + HOC(CH3)2 CH2CH3 (B) CH3CH2CH2OH + I – C(CH3)2 CH2CH3
(C) CH3 CH2CH2 I + I-C(CH3)2 CH2 CH3 (D) CH3 CH2 CH2OH + (CH3)2C=CHCH3
Q 30. Which of the following alcohols do not give white turbidity on treatment with HCl/ZnCl2?

(A) CH3CH2OH (B) CH2 OH

CH3
N C CH OH
(C) (D) H3C C OH
CH3
CH3
Q 31.
The ether O CH 2 when treated with HI produces

CH 2I CH 2OH
(A) (B)

OH I
(C) (D)
Q 32. Which of the following will result in the formation of an ether?
(A) (CH3)3 CO-Na+ + C2H5Br  (B) (CH3)3CBr + C2H5O-Na+
(C) C6H5O-Na+ + CH3Br  (D) C6H5Br + CH3O-Na+
Q 33. Which of the following reactions will give good yield of ether
OH (i) Na OC 2H5

(ii) C2H5Br
(A)
(i) Na
(CH3)3COH H5C6 O C(CH3)3
(ii) C6H5Br
(B)
(i) Na
(CH3) 3COH (CH3) 3C O CH2 CH2 CH3
(ii) CH3 CH2 CH2 Br
(C)
(i) Na
CH3 CH2 CH2 OH (CH3)3C O CH2 CH2 CH3
(ii) (CH3)3C Br
(D)
Q 34. In the reaction
OH
NaOH(aq) / Br2

The intermediate(s) is (are)

O O
Br

Br Br
(A) (B) Br
 O
O

(C) Br (D) Br
Q 35. Which of the following alcohols can be prepared by the action of a suitable Grignard reagent on an aldehyde or
ketone followed by hydrolysis?
(A) Ethyl alcohol (B) Methanol
(C) isopropyl alcohol (D) n-propyl alcohol
Q 36. Which of the following compound when reacts with phMgBr forms benzene
(A) CH3OH (B) CH4

(C) CH3  C  CH (D) OH

Q 37. With reference to the scheme given below, which of the given statement(s) about T, U, V and W is(are) correct?
O

H3C
LiAlH4
excess
CrO3 /H+ (CH 3CO)2O
V U W
(A) T is soluble in hot aqueous NaOH (B) U is optically active
(C) Molecular formula of W is C10H18O4
(D) V gives effervescence on treatment with aqueous NaHCO3.
Q 38. Which of the following reactions can be used for the preparation of alkyl halides?
(A) CH3CH2OH  HCl  anhy. ZnCl
2
 (B) CH3CH2OH  HCl 
(C) CH3 3 OH  HCl  (D)  CH3 2 CHOH  HCl 
anhy. Zncl
2



Q 39. Which of the following compounds will be gives a yellow ppt with iodine and alkali?
(A) Acetophenone (B) Methylacetate
(C) Acetamide (D) 2-hydroxy propane

Q 40. CH3 CH3 CH3 H

C C C C
H H H CH3
per acid per acid

A C
+
H /H2 O H+ /H2O

B D
Which of the following statements is/are true :
(A) B is a single compound and optically inactive
(B) D is a single compound and optically inactive
(C) B is an equimolar mixture of two enantiomeric compounds
(D) D is an equimolar mixture of two enantiomeric compounds
Q 41. 10 , 20 & 30 alcohols can be distinguished by
(A) Cu 573K (B) Victor Mayer test
(C) Conc. HCl ZnCl2 (D) Br2 Water
Q 42. Which of the following reagent can be used to prepare an alkylhalide form an alcohol?
(A) NaCl (B) HCl  ZnCl2
(C) SOCl2 (D) PCl5
Q 43.
CH3
CH3 H

H OH H

Which of the following represent conditions to perform given conversion?

(A) POCl3, pyridine
(B) Na-metal, CS2, heat

(C) C2H5ONa ,  H3C SO2Cl, pyridine; CH 3CH2O /CH 3CH2OH

( ) 
(D) CF3SO2Cl, pyridine; Me3CO K
Q 44. Which of the following will give yellow precipitate with I2 / NaOH?
O
(A) CH3  CO  O  CO  CH3 (B)
CH 3
I CH 2 C CH 2

OH
(C) CH3  CO  NH2 (D)
CH
CH 3 CH 2

CH 3
Q 45. C2H5OC2H5 and OH can be distinguished by :
(A) aq. FeCI3 (B) Na metal
(C) Tollen’s reagent (D) K2Cr2O7
Q 46. Predict the products in the following reaction

(A) P is (B) P is

(C) P is (D) Picric acid will be formed

Q 47. Which of the following ethers will get hydrolysed by HI?

(A) O (B) O

O O CH 3
O CH3
(C) (D)

Q 48. In the following reaction sequence, the structure of A and B are, respectively-

O H O
(A) and H (B) and
H

H
 and CHO
(C) OH (D) and
Q 49.

Compund ‘C’ is
(A) (B)

(C) (D)

Q 50. ** In the following reaction, predict the product (major)

(A) (B)

(C) (D)

Q 51. H
Br2+H2O NaOH NH3
** Product
Or (HOBr)
H3C

The product is:

H H2N
H 2N H
(A) (B)
H3C H3C
HO HO
H
HO
HO
H
(C) H3C (D)
H3C
H 2N
H 2N
Q 52. Phenol do not react with
(A) Sodium bicarbonate (B) Sodium hydroxide
(C) Potassiom hydroxide (D) Ferric chloride
Q 53. ** In the following reaction, predict the product (* means C-13)

(A) (B)

(C) (D)

Q 54. ** The major product of the following reaction is

 (A) (B)

(C) (D)

Q 55. When ethyl bromide is treated with moist Ag2O, main product is:
(A) Ethyl ether (B) Ethanol
(C) Ethoxy ethane (D) All of the above
Q 56. Which of the following alcohol shows fastest reaction with H +?

(A) (B)

(C) (D)

Q 57. ** Choose the correct statement(s) for the reaction

OH
O O

O 
AlCl3 / CS2
heat
HO
CH3 CH3
CH3
(b) (a)
O
(A) (b) is formed more rapidly at higher temperature (B) (b) is more volatile than (a)
(C) (a) is more volatile than (b) (D) (a) is formed in higher yields at lower temperature
Q 58. * Dehydration of cyclopentyl carbinol with conc. H2SO4 forms
(A) Cyclopentene (B) Cyclohexene
(C) Cyclohexane (D) None of these
Q 59. Identify the products in the following reaction and their configurations?
COOH
OsO4
H2O2
COOH COOH
COOH
H H OH

(A) (B)
COOH OH H
H OH
OH
COOH
COOH
COOH
H OH OH H
(C) (D)
H COOH H OH
COOH
OH
Q 60. O NaOH + I2 Ag, 
* x + y Z
CH 3 (yellow ppt)
Then compound ‘z’ is

(A) CHI3 (B) HC  CH

 O
(C)   (D) H2C  CH2
Ph C O Na
Q 61. Salicylic acid on bromination gives
(A) 2, 4, 6, - tribromo salicylic acid (B) 2, 4, 6, - tribromo phenol
(C) 2, 4, 6, - tribromo benzoic acid (D) p-bromo salicylic acid
Q 62. ** The end products of the reaction:
OH

CHCl3 50%
(X) (Y) + (Z)
KOH KOH

(Y) and (Z) are:

OH OH CH3 OH
COOK
(A) (B) OH
and

OH O
CH 2OH COOK
COOK
(C) and (D)

Q 63. * The major product of the following reaction is

(A) (B)

(C) (D)
Q 64. (i) CF3CO3H dil. H2SO4
A B
(ii) H2O 

A and B respectively are

OH OH
OH
(A) (B) and
and
OH
O O
OH OH OH
(C) (D)
and and
OH
Q 65. Which of the following compounds is oxidised to prepare methyl-ethyl ketone?
(A) 2-Propanol (B) 1-Butanol
(C) 2-Butanol (D) ter-Butyl alcohol
Q 66. O

(i) A C
CHO B
(ii) H3O+

Find the structure of A & C respectively

(A) Ph Mg Br and LiAlH4 (B) Ph  C  N and LiAlH4
 (C) Ph Mg Br and Na2Cr2O7 / H2SO4 (D) Ph  C  N and NaOH
Q 67. CH2 OH

H2SO4/H
A. The product A is:

CH2 HSO4 CH2

(A) (B)

CH3
CH3

(C) (D)

OH
Q 68. * About the following reaction
H3C
OH
H+ O3/Zn aq. NaOH
P Q R
 CH3COOH
Which of the following options (s) is/are correct? CH3

CH3
(A) Compound P is (B) Compound P is

O O
CH3
C
(C) Compound R is (D) Compound R is
CH3
Q 69. 1-Propanol and 2-Propanol can be distinguished by:
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling solution.
Q 70. OH OH
H+
Ph CH3
H H

OH
O
Ph
(A) (B)
O Ph

O H
(C) Ph (D) Ph
O
MgHg
Q 71. * In the following reaction, (CH3 )2 CO 
 A 
 B. dil.
H2 O H2 SO4

A & B respectively are :

(A) 2, 3 butanediol; 2-butanone
(B) 1,2 – ethane diol; glyoxal
(C) 2, 3 – dimethyl - 2, 3 – butanediol; 3, 3 – dimethyl – 2-butanone
(D) 2, 3-dimethoxy butane; propanone
Q 72. ** In the following reaction, final product is
14 NaOC2H5
CICH2 CH CH2
O

14 14
(A) CICH2 CHCH2 OC 2H5 (B) CICH2 CHCH2 ONa
OH OC 2H5
14 14
CH2 CHCH2 OC 2 H5 CHCH2 OC 2H5
(C) (D) CH2
O O

Q 73. Predict the major product

+ excess HI
O
(A) HO – CH2 – CH2 – CH2 – CH2 - I (B) HO – CH2 – CH2 – CH2 – CH2 - OH
(C) I – CH2 – CH2 – CH2 – CH2 - I (D) no reaction

Q 74. Phenol gives Reimer tiemann reaction with

(A) CH2CI2 (B) CCI4
(C) CHCI3& CCI4 (D) C6H5CH2CI
Q 75. Compound gives blood red colour in victor mayer test is
(A) a phenol (B) aldehyde
(C) nitroalkane (D) Nitrolic acid
Q 76. In the following sequence of reactions
P  I2
CH3CH2OH   A  
Mg
Ether
 B 
HCHO
C 
H2 O
 D The compound D is
(A) Propanal (B) Butanal
(C) n-Butylalcohol (D) n-Propyl alcohol
Q 77. O
O O
NaBH4
Product
*
O
H3C Cl
O

The Product in
O OH

(A) (B) CH3  CH2  OH

HO
OH
OH OH

CH3 O
(C) HO (D)
OH
O
OH O O
Q 78. An organic liquid A containing C, H and O has a pleasant odour with a b.p of 780 C. On boiling A with conc. H2SO4 a
colourless gas is produced which decolourises bromine water and alkaline KMnO4 . One mole of the gas also takes
one mole of H2 . The organic liquid A is:
(A) C2H5Cl (B) C2H5CHO
(C) C2H6 (D) C2H5OH
Q 79. Which one of the following is not the characteristic of alcohols?
(A) Their boiling points rise fairly uniformly with a rise in molecular weight
(B) Lower members have a pleasant smell but burning taste and the higher ones are odourless and taste less
(C) These are lighter than water
(D) Lower members are insoluble in water and organic solvents but the solubility goes on increasing with rise of
molecularweight
Q 80. Which is most easily dehydrated?

(A) OH (B) OH

(C) OH (D) OH

Q 81. Methyl alcohol on reacting with CH3CHO in presence of HCI forms.

(A) pseudonitrol (B) Hemiacetal
(C) epoxy ethane (D) Acetal
Q 82. 23 g of sodium metal shall react with methyl alcohol to give
(A) 1 mole of oxygen (B) 1 mole of H2
(C) ½ mole of oxygen (D) ½ mole of H2
Q 83. What reagent would be suitable for distinguishing 1-methoxy-3-methyl-2-butene from its isomer 4-methyl-3-penten-
1-ol?
(A) Bromine in methylene chloride (B) KMnO4 in aqueous base
(C) AgNO3 in dilute NH4OH (D) Sodium metal suspended in hexane
Q 84.
What is the product of the following process?
OH

SOCl2
Py

Cl Cl
(A) (B)
Cl

Cl
(C) (D)

Q 85. An organic compound A (molecular formula C6H12O does not change the color of acidic dichromate solution)
compound A on treatment with H2SO4 produces Alkene which on oxidative ozonolysis gives a molecule C6H10O3
which gives positive iodoform test . Find out structure of A.
OH
(A) OCH 3 (B)
CH 3

OH OH
(C) (D)
CH3

Q 86. C2H5MgBr reacts with ethanal to form a substance D. When D is heated with a solution of potassium dichromate in
dilute sulphuric acid what will the colour of the solution remaining after this reaction be?
(A) Orange (B) Yellow
(C) Blue (D) Green
Q 87. Propan-1-ol and propan-2-ol can be distinguished by their reaction with
(A) CH3MgBr (B) conc. HCI
(C) NaI (D) NaOI
Q 88. Arrange the following compounds in the decreasing order of their boiling pints in H 2O
Methanol ethanol butan-1-ol butan-2-ol
(I) (II) (III) (IV)
(A) I > II > III > IV (B) I < II < III < IV
(C) I > II > IV > III (D) III > IV > II > I
Q 89.
In the lucas test of alcohols, appearance of cloudiness is due to the formation of
(A) aldehyde (B) ketone
(C) acid chloride (D) alkyl chloride
Q 90. Di t-butyl ether is prepared best by the reaction
(A)  CH3  C  Br  CH3  COK  (B) CH3 3 C  OH 
H SO
2
180 C

0 4
3 3

CH  COH
(C) CH3 3 C  OH 
Al O
2
350 C 0
3 (D) CH3 2 C  CH2 
Conc
H SO

 
2 4
3 3

Q 91. ** When ethyl iodide is heated with dry silver oxide, the product formed is:
H2C CH2
(A) CH3CH2OH (B)
O
(C) CH3CHO (D) CH3CH2OCH2CH3
Q 92. The major product of the following reaction is

(A)

(B)

(C)

(D)

Q 93. * The major product in the following reaction is

(A) (B)

(C) (D) No epoxies observed

Q 94.
CH CH CH OH

3 2 2  x. Here X is
H SO 2 4

(A) (B)

(C) (D)

Q 95.

From the above reaction which of the following is correct.

(A) Acylation followed by only intermolecular mechanism
(B) Acylation followed by only Intramolecular mechanism
(C) Claisen rearrangement
(D) Acylation followed by intra as well as intermolecular mechanism
Q 96. An alkene obtained by the dehydration of an alcohol (A), on ozonolysis gives two molecules of acetaldehyde for
every molecule of alkene. The alcohol (A) is:
(A) CH3CH2CH2OH (B) CH3CH2OH
(C) CH3CH  CHCH2OH (D) H3C CH2 CH CH3
OH
Q 97. Tropylium cation is aromatic in nature
(A) True (B) False
Q 98. Solubility of n-alcohol in water decreases with increases in molar mass.
(A) True (B) False
Q 99. C2H5 OH have high boiling point than CH3OCH3.
(A) TRUE (B) FALSE
Q 100. ** Anisole is less reactive than phenol towards electrophilic substation reactions.
(A) True (B) False
Q 101. Tollen’s reagent but not Fehling’s solution can be used to distinguish between acetaldehyde and benzaldehyde.
(A) True (B) False
Q 102. STATEMENT 1: The C – O – C bond angle is higher in ether than H – O – H bond angle in water.
STATEMENT 2: Oxygen is sp3 – hybridized in both ethers and water.
Q 103. How many –OH group will react towards H+ - ion

Q 104. Identify unknown compounds A, B …H in the following series of reactions:

OH 
H2SO4
A 
NBS
 B 
LiAlD4
C

PBr5

D 
1. Li
2. CuI
 E 
NBS
 F 
H 2 / Ni
 G 
alcoholic KOH
H
3.B
Q 105. (a) Convert the following
(i) Phenol to picric acid
(ii) Benzene to phenol
(iii) Acetic acid to ethanol
(iv) Ethanol to ether
(v) Toluene to Benzene
(vi) Benzene to acetophenone
(b) Explain the esterification reaction of ethanol with mechanism.
(c) Write the names & structures of three isomers which have the same molecular formula C 3H8O.
Q 106. How many of the following ethers can be synthesised by typical Williamson’s reaction?
R2 CH  O  CHR2 , R3C  O  CR3 , R3C  O  CHR 2
C6H5  O  C6H5 , R  CH  CH  O  CH  CH  R
R3C  CH2  O  CH2  CR3