EXERCISE-I(A)

Q.1 Which of the following reaction is called as BouveaultBlanc reduction (A) Reduction of acyl halide with H2PdBaSO4 (B) Reduction of ester with Na/C2H5OH (C) Reduction of anhydride with LiAlH4 (D) Reduction of carbonyl compounds with Na/HgHCl Glycol on treatment with PI3 mainly gives (A) Ethylene (B) Ethylene iodide

Q.2

(C) Ethyl iodide

(D) Ethane

Q.3

Acrolein is formed when glycerol is heated with (A) Acidified KMnO4 (B) Br2 water (C) KHSO4 Glycerol on treatment with oxalic acid at 110C forms (A) Allyl alcohol (B) Formic acid (C) CO2 and CO

(D) HNO3 (D) Glyceric acid

Q.4

Q.5

If the starting material is 1methyl1,2epoxy cyclopentane, of absolute configuration, decide which one compound correctly represent the product of its reaction with sodium methoxide in methanol.

(A)

(B)

(C)

(D)

Q.6

When phenol is treated with PCl5, the yield of chlorobenzene is generally poor because of the formation of (A) Benzoyl chloride (B) pchorophenol (C) ochlorophenol (D) Triphenyl phosphate In the following reaction, final product is
H ClCH 2 CH C H 2 NaOC 2 5 \ / O

Q.7

14

14

14

(A) ClCH 2CH C H 2OC 2 H 5 | OH (C) C H 2 CHCH 2 OC 2 H 5 \ / O

14

(B) ClCH 2CH C H 2ONa | OC 2 H 5 (D) CH 2 CH C H 2OC 2 H 5 \ / O

14

Q.8

Consider the reaction of HI with the following: I II (D) none

Which forms di-iodide on reaction with HI (excess)? (A) I and II both (B) II only (C) I only Q.9

Ethanol on reaction with acetic anhydride gives (A) Acetic ester (B) Formic ester (C) Ethanoic acid (D) Acetic ester and Ethanoic acid both Ethanol cannot be dried by anhydrous CaCl2 due to formation of the following solvated product (A) CaCl22C2H5OH (B) 2CaCl23C2H5OH (C) CaCl23C2H5OH (D) CaCl2C2H5OH Rate of hydration of

Q.10 Q.11

, will be in order: (A) I < II < III Q.12 Q.13 Q.14 Q.15 Q.16

(B) I < III < II

(C) II < I < III

(D) III < II < I

The reaction of CH3OC2H5 with HI gives (A) CH3I (B) C2H5OH

(C) CH3I + C2H5OH (D) C2H5I + CH3OH

The number of methoxy groups in a compound can be determined by treating it with (A) HI and AgNO3 (B) Sodium carbonate (C) Sodium hydroxide (D) Acetic acid Most acidic alcohol out of following compounds is (A) (CH3)3COH (B) CH3CH2OH (C) CH3OH Action of HNO2 on CH3NH2 gives following as major product (A) CH3OH (B) CH3OCH3 (C) CH3ON=O (D) PhOH (D) CH3NO2

A compound X with molecular formula C3H8O can be oxidised to a compound Y with the molecular formula C3H6O2, X is most likely to be (A) Primary alcohol (B) Secondary alcohol (C) Aldehyde (D) Ketone Diethyl ether and air gives ether hydroperoxide. The mechanism of the reaction is (A) Nucleophilic substitution (B) Free radical addition (C) Free radical substitution (D) None of the above Ether on carbonylation gives (A) Alkanoic acid (B) Alkanone

Q.17

Q.18

(C) Alkyl alkanoate

(D) Alkanal

Q.19

I R O R ' RI + R'OH true about this mechanism | H

(A) SN1 in gas phase (C) both of the above Q.20 Phenol with Hinsbergs reagent gives (A) Sulphone (B) Sulphanilic acid

(B) SN2 in aqueous phase (D) none (C) Sulphonic ester (D) Sulphonal

Q.21

Select the odd structure out (A) CH3CH(OH)CH2CH3 (C) CH3CH(OH)CH3

4 Glycerol 4 A B A and B are: (A) Acrolein, allyl alcohol (C) Allyl alcohol, acrolein

(B) CH3CH(OH)CH2CH2CH3 (D) CH3CH2CH(OH)C2H5

Q.22

KHSO

LiAlH

(B) Glyceryl sulphate, acrylic acid (D) Only acrolein (B is not formed)

Q.23

An ether is heated with phosphorous penta sulphide to give (A) Alkanthiol (B) Dialkyl sulphide (C) Hydrogen sulphide (D) Thioester
O i ) NaOH Phenol ( A 2 B Al2 C 3 H+ / H O

Q.24

( ii ) CO 2 / 140C

CH3COOH ,

In this reaction, the end product C is: (A) salicylaldehyde (B) salicylic acid Q.25

(C) phenyl acetate

(D) aspirin

In the Liebermanns nitroso reaction changes in the colour of phenol occurs as: (A) Brown or red-greenish red-deep blue (B) red-deep blue-green (C) red-green-white (D) white-red-green

Q.26

A. A is
H 3O

(A)

(B)

(C)

(D)

Q.27 A and B are: (A)

cold A CrO3 B alkaline KMnO

4

AcOH

(B)

(C)

(D) no formation of A and B

Q.28

B 4

NaBH

2 CH = CH CHO A

H / Pt

A and B are: (A) (B) (C) (D) CH2CH2CHO, CH2CH2CH2OH, CH = CHCH2OH CH = CH CH2OH

CH= CHCH2OH in both cases CH2CH2CH2OH in both cases

Q.29

3 B

CH OH

2 A

H O18 H+

CH 3ONa

A and B are CH 3 | (A) CH 3 C CH 2 | | OH OH 18

CH 3 | , CH 3 C CH 2 | | OH OCH 3

CH 3 CH 3 | | (B) CH 3 C CH 2 , CH 3 C CH 2 | | | | OH18OH OH OCH 3

CH 3 CH 3 | | (D) CH 3 C CH 2 , CH C CH 3 2 | | | | 18 OCH 3 OH 18OH OH

CH 3 CH 3 | | (C) CH 3 C CH 2 , CH 3 C CH 2 | | | | 18 OH OH OH OH 18
18

Q.30

Oxalic acid + A hence A conc. H 2SO 4 B, B is: (C) CH 2 O CH 2 | | OH OH

(A)

(B)

(D) None

Q.31

Select schemes A, B, C out of I acid catalysed hydration (A) I in all cases (B) I, II, III Q.32 Dehydration of the alcohols

II

HBO (C) II, III, I

III

oxymercuration-demercuration (D) III, I, II

will be in order (A) IV > III > II > I

(B) I > II > III > IV

H O+

(C) IV > II > III > I

(D) II > IV > I > III

Q.33

CH3MgBr + E is (A)

HCHO HBr Mg / ether 3 HI A B C D E H O+

3

(B)

(C)

(D)

Q.34

H ? Product is:

(A)

(B)

(C)

(D)

Q.35 (A) (C)

Alc. Major product is KOH (B) (D)

Q.36

RMgX ? Product Obtained is:

H 2O

R | (A) R 'C CH 2OH | R''

R' R R | | | (B) RCH 2 C OH (C) R ' CH 2 C OH (D) R ' ' CH 2 C OH | | | R' ' R' R''

Q.37

I / NaOH

+ A, A is H

(A)

(B)

(C)

(D)

Q.38

3 (A)

CH OH CH3O

3 (B) A & B are:

H 2SO 4

CH OH

(A)

&

(B)

&

(C)

&

(D)

&

Q.39

3 ? Major Product is:

AlCl

(A)

(B) H3COC

OH

(C)

(D)

Q.40

? Product is:

(A)

(B)

(C)

(D) no reaction

Q.41

3 [X] here X is:

( i ) CHCl + KOH

(ii ) CH 2I 2 + NaOH

(A)

(B)

(C)

(D)

Q.42

(CH 3 ) 2 C C(CH 3 ) 2 | | OH OH (A) OH at C2 is more basic than that of at C5 (B) OH at C2 is more acidic than at C5. (C) both have same basicity (D) both have same acidic strength . In this diol
2 (CH3)2C = C(CH3)2 A OH B

Q.43

H 2O

(A)

(B) (CH 3 ) 2 C C(CH 3 ) 2 | | OH Cl (D) None

(C)

Q.44 A is

2 A

NaNO HCl

(A)

(B)

(C)

(D)

Q.45

CH 2 = CHCHCH 2CH 2OH | OH (A) CH 2 = CHCCH 2 CH 2OH || O

A. A is

(B)

(C)

(D)

Q.46

HCO 3H H3O Acetophenone A B + C Indicator (D) +

Pthalic Anhydride H

C & D are

(A) CH3OH &

(B) PhOH &

(C) PhOH &

(D) CH3OH &

MnO CH 2 CHCHCH 2CHO CHO =2 CHCCH 2O || || CH 2 = CHCCH 2COH OH O || O

Q.47

m-Aminophenol on treatment with NaOH and CO2 gives which of the following as major product?

(A)

(B)

(C)

(D)

Question No 48 to 50 (3 questions)

Q.48

Compound 'B' is? (A) (B) (C) (D)

Q.49

Organic compound A does not undergo de carboxylation reaction because? (A) Intermediate does not follow Saytzeff'n rule (B) Intermediate does not follow Hofmann's rule (C) Intermediate does not follow Bredict's rule (D) Intermediate does not follow MarkwoniKoffs rule Total No. of stereoisomers of B are? (A) 2 (B) 4 (C) 3 (D) 6

Q.50

EXERCISE-I(B)
Q.1 Compound which gives alcohol on reduction is/are (A) Me C Cl || O Q.2 (B) (C) (D)

Phenol and ethanol are distinguished by the reaction with (A) Red litmus (B) NaHCO3 (C) FeCl3
H

(D) NaOH

Q.3

dil. H 2SO 4 2 2O In the reaction sequence, CaC2 H A B C, true about the product C is +2 Hg Ni

(A) give yellow ppt. with NaOI (B) its final oxidation product is carbonyl compound (C) its final oxidation product is CO2 and H2O (D) its final oxidation product is CH3COOH Q.4 Which can be cleaved by HIO4? O O || || (A) CH CH CCH CCH 3 2 2 3 OH O O | O Me C CH 2 CH NH |2| | |||\ /| | (B) CH 3CHCCH CH Me O O Me2 3 C OC O O || || (D) CH 3CCH 2 CHCH 2CCH 3 | OH

(C)

Q.5

HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in (A) (B) (C) (D)

Q.6

Diethyl ether reacts with PCl5 to form (A) Ethyl chloride (C) Ethenol

(B) Phosphorous oxy trichloride (D) Ethene

Q.7

Select the correct synthesis products (A)

2 2 3 NaOH

BH THF

H O , OH

(B)

2 4 NaOH

Hg ( OAc) H 2O

NaBH

(C) (D) Q.8

mCPBA
CH 2Cl2

The molecules of ether dehydrates in the presence of (A) Al2O3 (B) H3PO4 (C) H2S2O7 Anhydride of alcohol is (A) Ether (C) Alkyl hydrogen sulphere (B) Aldehyde (D) Alkene

(D) liq. NH3

Q.9

Q.10

Lucas test is used to make distinction between 1, 2 and 3 alcohols ROH + HCl anhydrous ZnCl 2
conc.

RCl
White turbidity

+ H2O

This shows that (A) ROH behaves as a base (B) greater the value of pKa (alcohol), greater the reactivity with conc. HCl and thus sooner the formation of white turbidity. (C) alcohol which reacts fastest with Na metal, will give turbidity at fastest rate (D) alcohol which gives red colour during Victor Mayor test, will give turbidity at slower rate then those giving blue or white colour during Victor Mayor test. Q.11 If ethanol dissolves in water, then which of the following would be done (A) Absorption of heat (B) Emission of heat (C) Increase in volume (D) Contraction in volume Which method is useful for the synthesis of ether? (A) (B) C2H5ONa + (CH3)2SO4 (C) CH3ONa + CH3CH2OSO2 (D) (CH3)3CBr + CH3CH2ONa Q.13 Which of the following can react with TsCl (A) Glycerol (C) Oil of wintergreen (B) Oximinoacetone (D) dimethyl amine aq. NaOH

Q.12

Q.14

Which is/are correct statements? (A)

(B)

(C) This is only affected in reduction to 2 alcohol

NaBH

CH3OH

(D)

Q.15

3-methyl-3-hexanol can be prepared by (A) CH3MgI and 3-hexanone, followed by hydrolysis (B) C2H5MgI and 2-pentanone, followed by hydrolysis (C) C3H7MgI and 2-butananone, followed by hydrolysis (D) C4H9MgI and propanone, followed by hydrolysis In which cases product formed are not according to reaction? (A) (B) + HNO3 H 2SO 4 + HNO3 H 2SO 4

Q.16

(C) CH2 = CHCHO + LiAlH4 CH3 CH2CH2OH (D) Q.17 + CH3ONa

Dehydration of alcohols take place more rapidly with POCl3 than with H2SO4. Select the correct statement(s) about the following dehydration reaction.
3

POCl

pyridine

(A) It does not involve carbocation. (B) It involves ROPOCl2 with OPOCl2 as a better leaving group. (C) It involves E2 mechanism as pyridine base abstracts proton from the adjacent carbon as the same time at which OPOCl2 is leaving. (D) It is E1 reaction without formation of carbocation.

Q.18

Which of the following will get oxidised by Br2 / KOH into carboxylic acid? (A) CH3CH2OH (B)
CH CH 3 | OH

(C) Q.19

CH2OH

(D)

In Kolbe-Schmidt reaction, o-hydroxy benzoic acid is predominantly formed. This is because (A) salicylate anion is a stronger base than phenoxide ion (B) salicylate anion is a weaker base than phenoxide ion (C) p-hydroxy benzoate ion is a stronger base than phenoxide ion (D) p-hydroxy benzoate ion is a stronger base than salicylate ion Methanol can be distinguished from ethanol by (A) Heating with I2 and alkali (B) Treating with schiffs reagent (C) Treating with CrO3 solution in dil. H2SO4 (D) Treating with Lucas reagent Products form by following reactions are

Q.20

Q.21

CHCl +KOH

(A)

(B)

(C)

(D)

Q.22

For the reactions shown below, identify the correct statement(s) with regard to the products formed: (i) MeOH, P H
+

(ii)

NaOMe Q / MeOH

(A) P and Q are identical (B) P is recemic and Q is optically active (C) P and Q are positional isomers (D) both are optically active Q.23
Tilden NaNO2 NH C2N5NH2 (i) 3 (ii) (iii). The product (iii) can be reagent

HCl

(A) Alcohol

(B) Ether

(C) Alkyl chloride

(D) Alkyl nitrite

Q.24

Products form during dehydration of following alcohols are

(A) Q.25

(B)

(C)

(D)

Consider the following compound A (below)

Select the correct statement(s) (A) It is more acidic than CH3OH (C) It reacts very fast with Lucas reagent Q.26 Match the following: Reaction (A)
2 4

O || (B) It is more acidic than CH 3COH (D) It is a diacid base Mechanism

Conc.H SO

(P)

change in number of carbon in cycle

(B)

HIO

(Q)

Pinacol rearrangement

(C)

H
heat H O heat

(R)

Oxidative bond cleavage

(D) Q.27

(S)

Ketone as product

Match the column: Column I (A) Identification of 1, 2& 3 Alcohols (B) Identification of 1, 2& 3 Nitro alkanes (C) Formation of alcohol by anti Markovnikov's addition of H2O (D) Formation of alcohol by Markovnikov's addition

(P) (Q) (R) (S) (T)

Column II Oxymercuration demercuration Cu/300 heat Victor Mayer's test Hydroboration oxidation Lucas test

Q.28

Match the column: Column I (A) Oxidation of 1alcohol in aldehyde (B) CrO3 . .HCl

(P) (Q)

Column II KMnO4/ Collin's reagent

(C) (D) Q.29

CrO3 .2 Oxidation of alkene into acid

(R) (S)

Jone's reagent P.C.C

Match the products of following: Column I (A) (B)

HI

Column II (P) (Q) I CH2OH

Violet color is obtain by the reaction of neutral FeCl3 with

(C)

Reaction of benzaldehyde with LiAlH4 / H2O gives

(R)

OH

(D)

+ KI ?

Q.30

CH 3 CH CH = CH 2 | CH 3
which is true about alcohol and R? Alcohol (A)

(S) CH2 I CH 3 agent R CH CH 3 CH Re OH | | CH 3 CH CH 2CH 3 C OH 3 Alcohol | CH 3

Reagent B2H6 , H2O2 / NaOH

CH 3 CH CH 2 CH 2OH | CH 3

(B)

PdCl2, H2O, O2 / LAH

(C)
OH | CH 3 C CH 2CH 3 | CH 3

Hg(OAc)2, H2O / NaBH4

(D)

dil. H2SO4