Questions Chapter 1-10

7/25/2019 Questions Chapter 1-10

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SECTION - I : STRAIGHT OBJECTIVE TYPE

1.1 IUPAC name of compound

CI

Br

is

(A) 3-Bromo7-chloro-7ethyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-3-methylnonane(B) 3-Bromo7-chloro-5-(1,1-dimethyethyl)-7-ethyl-3methyl-5-(2-methylpropyl)nonane(C) 3-Bromo7-chloro-7ethyl-3-,methyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)nonane(D) 3-Bromo-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-7-chloro-7ethyl-5--3-methylnonane

1.2 Which of the following structure\s is the correct structure of 3-ethyl-5, 5-diisopropyl-7-methlnonane

(A) (B)

(C) (D)

1.3 The correct IUPAC name of the folllowing compound is

(A) 5,6-Diethyl-8-methyl dec-6-ene (B) 5,6-Diethyl-3-methyl dec-4-ene(C) 5,6-Diethyl-3-methyl dec-4-ene (D) 2,4,5-Triethylnon-3-ene

1.4 Correct IUPAC name of the following compound is :

HO

Br

(A) 3-(Hepta-2,4,6-trienyl)-4 bromo cyclopenta-2, 4, -dien-1-ol

(B) 7-(2-Bromo-4-hydroxy cyclopenta-1,4-dienyl)hepta-1,3,5-triene

General Organic Chemistry-I

(GOC-I)

1


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(C) 7-(5-Bromo-3-hydroxycyclopenta-1,4-dienyl)hepta-1,3,5-triene(D) 3-Bromo-4-(hepta-2,4,6-trienyl)cyclopenta-2,4-dien-1-oll

1.5 The IUPAC name of the compound

Br

will be :

(A) Tropyluim bromide (B) 1-Bromocyclohepta-2,4,6-triene(C) 3-Bromocyclohepta-1,4,6-triene (D) 7-Bromocyclohepta-1,3,5-triene

1.6 Correct IUPAC name of the co,pound H C CH O C3 2 O C CH CH2 3

O O(A) 4-(Ethyl methanolyonxy)phenylpropanoate(B) Ethyl 4-propanoyloxybenzenecarboxylate(C) 4-(1-Oxo-2-oxabutyl)phenylpropanoate

(D) 1-(1-Oxo-2-oxbutyl)-4-(1-oxopropoxy)benzene

1.7 Correct IUPAC name of the compound

Et

Me

O

O is

O

(A) 2-Ethyl-3-methylbut-2-ene-1,4-dioic anhydride(B) 3-Ethyl_2-methylbut-2-enedioic anhydride(C) 2-Ethyl-3-Methyl-1,4-diketobut-2-enoic anhydride

(D) 2-Ethyl-3-methylcyclopenatanoxy-1,4-dione

1.8 The IUPAC name of the following compound is

COCl

COOC H2 5

(A) 2-(Ethoxycarbonyl) benzalychloride (B) Ethyl 2-(Chloroformyl)benzoate(C) Ethyl 2-(chloromethanoyl)benzoate (D) Ethyl2-(Chorocarbonyl)benzene carboxylate.

1.9 IUAC name of

Cl

Br

CH3

C H52

(A) 4-Bromo-6-chloro-2-ethyl-1-methylcyclohex-1-ene(B) 5-Bromo-1-chloro-3-ethyl-2-methylcyclohex-2-ene(C) 5-Bromo-3-chloro-1-ethyl-2-methylcyclohex-1-ene(D) 1-Bromo-5-chloro-3-ethyl-4-methylcyclohex-3-ene

1.10 A hydrocarbon (R) has six membered ring in which there is no unsaturation. Two alkyl groupsare atttached to the ring adjacent to each other. One group has 3 carbon atoms with branchingat 1st carbon atom of chain and another has 4 carbon atoms. The larger alkyl group has mainchain of three carbon atoms of which second carbon is substituted. Correct IUPAC name ofcompound (R) is

(A) 1-(1-Methylethyl)-2-(1-methylpropyl)cyclohexane(B) 1-(2-Methylethyl)-2-(1-methylpropyl)cyclohexane


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(C) 1-(1-Methylethyl)-2-(2-methylpropyl)cyclohexane(D) 1-(1-Methylethyl)-2-butylcyclohexane

1.11 Identify the structure of x,

CH C CH3 C H + H C H + CH C C CH C H2 2

O O O O O O

CH3 CH3

CH3

H /Ni2

Zn/H O2

O3

X

(A) (B) (C) (D)

H C3

1.12 In the given sequence reaction which of the following is the correct structure of compounds A.

O O

OO

H

H+ HCHO

H / Ni2

(i) O3

(ii) Zn / H2O

A(C H )10 14

(A) (B) (C) (D)

H

1.13 For the following reactions sequenceHOOCCOOH

O3H2O2

C7H10H2 / Niexcess

Y

C7H12X

The structure consistent with X and Y are:

(A)

(B)

(C)

(D)

'Y' 'X'


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1.14 An organic hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Itsstructure is

(A) (B) (C) (D)

1.15 CO

O

HCO

O

and are

(A) Position isomers (B) Chain isomers(C) Functional isomers (D) Metamers

1.16 In which reaction a chiral reactant is giving a chiral product.

C = O + H2 H C OHHint :

(D)

H Cl

C = O

CH3

H Cl

CH3

H / Ni2H CH CH2 3

CH = CH2

CH2OH

O / Zn / H O3 2

H C = C

HOC

CH3

(B)

H CHO

CH3H

HKMnO / OH /4

C C H2 5

CH3

H Reductive ozonolysis

(i) O

(ii) Zn / H O

3

2

1.17 Which of the following statements is true abnout the follownig conformer (X)?

I

CH3

COOH

I

COOH

(X)

CH3

(A) (X) is the most stable conformer of meso-2,3-Diiodo-2,3-dimethylbutanedioic acid

(B) The most stable conformation will beCH3

CH3

COOH

COOH

I

I

(Y)

(C) The dipole moment of (X)is not zero but that fo Y is zero.(D) None

1.18 An unsaturated hydrocarbon on jcomplete hydrogenation gives 1-isopropyl-3 methylcyclohexane,after ozonolysis it gives one mole of formaldehyde, one mole of acetone and one moleof2,4-Dioxohexanedial. The possible structure\s of the hydrocarbon maybe


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(A) (B) (C) (D)

1.19 How manyh assymmetric carbon atoms are present in

(i) 2-Dimethyl cyclohexane(ii) 3-Methyl cyclopentene(iii) 3-Methylcyclohexene(A) 2,1,1 (B) 1,1,1 (C) 2,0.2 (D) 2,0,1

1.20 Which of the following statements is not correct?(A) A compound whose molecule has D configuration will always be dextrorotatory(B) A compound whose molecule has D configuration may be dextrorotatory or levorotatory(C) A compound whose molecule has R configuration may be dexrotatory or levorotatory(D) A compound whose molecule has L configuration may be dextrorotatory or levorotatory

1.21 Identify the pair of enantiomers amongst the given pairs:

(A) D OH,

COOH

CH3

HOOC OH

CH3

D

(B) HO CH ,3

Ph

H

HO Ph

CH3

H

(C) H OH ,3

COOH

CH

HOOC CH3

OH

H

(D) H OH,

CH3

HO Ph

CH3

CH3 CH3

1.22 The stereochemical formula of deiastereomer 'Y' of optically active compound 'X' is:

X=2,3-Dihydroxbutanedioic acid.

(A) HOOC HOH

OH

H COOH

(B) HOOC H

OH

H

COOH

OH

(C) H OH

COOH

HO

COOH

H

(D) HO COOH

H

H

OH

COOH

SECTION-II : MULTIPLE CORRECT ANSWER TYPE1.23 Which of the followning statements are not correct?

(A) A meso compound has chiral centres but exhibits no optical activity(B) A racemic mixture is optically inctive becaure of two equal and opposite rotation of same

molecules in mixture.

(C) A meso compound has molecules which are superimpossable on their mirror images eventhough they contain chiral centres

(D) A meso compound is optically inctive because the rotation caused by any molecule iscancelled by and equal and opposite rotation caused by another molecules that is the mirrorimage of the first

1.24 Consider following compounds

OH

C H2 5(I)

OCH3

CH3(III)

OH

CH CH3

(II)

CH2OCH3

(IV)


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Choose the correct statement(s)from the following(A) I,II and III are functional isomers (B) I and II re position isomers(C) III and IV are chain isomers (D) III and IV are metamers

1.25 Which of the following statement\s is \are true about the following compounds

O

(I) (II) (III)O O

(A) (I)and (III)are structural isomers. (B) (I)and (II)are geometrical diastereomers(C) (II)and (III)are strukctureal isomers (D) (I)and (II)are jidentical

1.26 Which of the following is\are a meso compoumd.

(A)

OHOH

O

CH OH2

CH OH2 (B)

COOH

H

COOHNH2NH2H

(C)

CI

F

Br

CI

Br

F

COOH

(D)

COOH

H OH

HO H

1.27 Which of the following pair represents the correct relationshipI II

(A)

NH2

CI

OH CI OH

NH2

Relationship

(B)

Positional Isomers

Chain Isomer

(C)

(D)

NH C H3 7 H C N C H3 2 5

Functional Isomers

Metamer IsomersCH CH CH COCH3 2 2 3

O

CH CH3 2 2 3COCH CH

O

SECTION-III:REASONING TYPE

1.28 Statement-1:Restricted rotation about a bond is the necessary condition for geometricalisomerism.Statement-2:Two different orientations are possible due to restricted rotation about a bond iftheend groups are different.(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1.(C) Statement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement -2 is True.


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1.29 Statement-1:Aracemic mixture of 2-Chloropropanoic acid is treated with excess of (+)-2-Butanol.The reaction can be represented as follows:

CH3CHCOOH + CH3CHCH2CH3 CH3CHCOOCHCH2CH3+CH3CHCH2CH3

CI OH(+)excess CI OH(+)(Left unreacted)

Statement-2:The solution kjof reaction mixture at time(t = 0), will be dexterorotatory becauseof (+)2-butanol(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1.(C) Statement-1 is True, Statement-2 is False.(D) State,emt-1is False, Statement-2 is True.

SECTION-IV : TRUE & FALSE STATEMENT TYPE1.30 The products(ester)of following reactiongive diastereomers

Me

HD

Me

EtH

COOH + HO H SO2 4

Comprehension #1

Compound X(C7H14O4)on ozonolysis gives (Y) and (Z),(Z) is the aldhyde which gives only oneoxime with NH2-OH. On treatment with I2\NaOH,(Y)gives yellow solid CHI3alongwith compoundgiven below.

HO

HH OH

OH

H

COONa

CH OH2

When (X)is treated with D2\Ni, it gives two optically active compound.(V)and (W).

1.31 compound(V)and (W)are(A) Enantiomers (B) Diastereomers (C) Identical (D) Nuclear Isomers

1.32 Compound (Y)can give........ type of oximes on treatment with NH 2-OH(A) 2 (B) 6 (C) 8 (D) 7

1.33 Which of the following statement is true(A)'X' gives positive test with 2,4-DNP and Br2solution(B)Y gives positive with both 2,4-DNP and tollens reagent(C)Compound(V)give positive test with NaHCO3

(D)

CH3 NH2C

O is the isomeric amide of oxime of next higher homolog of Z.

Comprehension#2

Structural isomers have different covalent linkage of atoms. Stereoisomers are compounds thathave same sequence of covalent bonds but differ in the relative dispositions of their atoms in

space. Geometrical and optical isomers are the two important types of configurational isomers.The compound with double bonds or ring structure have restricated rotation, so exist in two


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geometrical forms. The double bonds in larger rings (ring size 10 carbon or large) can alsocause geometrical isomerism. The optical isomers rotate the plane of plane-polarised light. Asp3

hybridised carbon atom bearting four different types of substituents is called and asymmericcentre or chiral centre. A chiral object or molecule cannot be superimposed on its mirror image.Stereoisomers that are mirror images of each other are called diastereomers. Deastereomersw

have different physical properties.A racemic mixture is optically inctive and contains equal amounts of both the enantiomers .Resolution refers to method of separating a racemic mexture into two pure enantiomers. Amesocompound is and opticall incactive stereoisoker, which is achiral due to the presence ofand internalk plane of syummetry or centre of symmetry within the molecule.

1.34 The pair showing identical species is

H

H

COOH

OHOH

HOOC

(C) and

COOHOH

H OHHHOOC

CCH3

Cl

Br

H

CH3C

Cl

Br

Hand(D)

(B)H

D

OH

Br

Me

Et

D

H

Et

OH

Br

Me

and(A) H

Cl

H

Cl

and

1.35 Observe the following reaction

H

CH3

NH2

*+

HOOC CH3

Cl H

C*

(R')-1-Phenylethylamine (R+S)-2-Chloropropanoic acid

(R' R) + (R' S)(1)

(R')+ (R)

(R')+ (S)

(R'R)

(R'S)hydrolysis

hydrolysis

(3)

(3)

separation by

recrystallisation(2)

Which statement is not correct about the above observation.(A)The product mixture os step-1 is optically active(B)The products R'R and R' S have identical structural formul.(C)R'Ris nonsuperimposable on R' S(D)R'Rand R' S have same solubillity in water.

1.36 The number of chiral centres present in the following compound is

HH

OH

H

H

H

HO

O

OH

CH OH2

O

OHOH C2

H

H

OH H

OH

CH OH2

D (+) - Sucrose


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(A) 7 (B) 8 (C) 9 (D) 10

SECTION-VI:MATRIX-MATCH TYPE

1.37 Column I may match with more than one conditions of column II.

Column I Column II

Ph CH = CH Ph(A) (p) Ozonolysis followed by reaction withNH2 OH leads to more than one oximeproduct

(CH ) C = CH CH = Cl23

CH3

(B)

(q) Can exhibit geometrical isomers

CH = CH CH = CH2 2 (r) Compounds with this structure formula

can be separated into different fractionsupon fractional distillation

CHO CH CH CHO

OH OH(s) Is capable of showing stereoisomerism

1.38 Column I Column II

(A)HO

D

D

D

OH

CH3 OH

D

D

D

OH

H3C(p) can be separated by fractional

crystallisation

(B)CHO

C CCH3

CH3

CHO

CHO

C CCH3

CHO

CH3

(q) Can not be separated by

fractional crystallisation

(C)

COOH

OH

OHCOOH

H

H

H

HOH

OH

COOH

COOH

(r) Optically resolvable

Cl

OH3

OH2ID

Br

H

CH3

Br

CH2ClI

D

H

(D) (s) donot have identical boilling point


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SECTION-VII: SUBJECTIVE ANSWIR TYPE

SHORT SUBJECTIVE:

1.39 Total number of stereoisomes possible for molecule A will be

H C3 CH = CH CH = CH

1.40 A BCl / hv2Fractional

distillation

Number of possible fractions of B are:

1.41 The number of isomers for the compound with molecular formula C2HDFCI is :

1.42 Number of sp2

-sp2

sigma bonds in viven compound A is:

1.43 Write lowest molecular weight of saturated cyclic hydrocarbon which has four substtituents.Molecular weight=98.


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SECTION-I: STARINGT OBJECTIVE TYPE

2.1 Choose the correct statement

(A) I effect transfers e from one carbon atom to another

(B) I effect operates in both \p bond(C) I effect creates not charge in moecule(D) I effect cteates prtial cjarges and it is distance dependent

2.2 The correct stability order of following species is :

(x) (y) (z)

C

(w)

(A)x>Y>w>z (B)y>x>w>z (C)x>w>z>y (D)z>x>y>w

2.3 Which of the following does not represent the resonating structure of

(A) (B)

+

+ + (C) (D)

2.4 The most stable resonating structure of CH O = CH = CH3 2:

(A) (B) H C O = CH CH3 2 (C) H C O = CH CH3 2 (D) H C O = CH CH3 2+ + + +

2.5 Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but in compoundP double bond between two rings was observed by NMR to have a rotational energy barrier ofonly about 20 cal.\mol., showing that it has lot of single bond charcter.

nC H3 7

nC H3 7

The reason for this is(A) Double bond having partial triple bond charcter because of resonance(B) Doule bond undergo flipping(C) Double bond having very high single bond charcter because of aromaticity gained in both

three and five membered rings.

(D) +I effect of nC3H7groups makes double bond having partial single bond charcter.

General Organic Chemistry-II

(GOC-II)

2


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2.6 Most contributing structure in nitroethene is

(A) CH = CH N2+ O

O

CH = CH N2+ O

O

+ CH CH N2

+ O

O

+CH CH = N2

+ O

O

+(B) (C) (D)

2.7 In which of the followig molecules all the effects namely inductive, mesomeric and hyperconjjgationoperate:?

(A) Cl (B) CH3

CH3

(C) COCH3

CH3

(D)

2.8 Between

N

CH3CH3H3C +

N

HHH +

and

(l) (ll)

(A) N(I)has more 's' charcter in NCH3 bonds(B) N(II)has more 's' charcter in NH bonds(C) N(I)has less 's' charcter in NCH3 bonds(D) None of these

2.9 The acid strength order is:

O

O OH

OH

I II

OH

C

O

OHHO

III

C

O

CH3CH3

IV

(A)I> IV> II> III (B)III> I> II> IV (C)II >III> I>IV (D)I >III >II> IV

2.10 Acid strenght of the conjugate acids of the following are-

N NH N NH N

H

(l) (ll) (lll) (lV)

N

(A)I> II> III >IV (B)III> II> I> IV (C) IV> III> II> I (D)None of these

2.11 The acid dissociation constants of the following acids are given as under:Compound Ka

CICH2COOH 136 X 105

CH3CH2

CI

C HCOOH 139 X 105

CH3

CI

C HCH2COOH 8.9 x105

CI

C H3CHCH2COOH 2.96 x105

CH3CHCH2COOH 1.52 X 105


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From this data, the following obnservations can be made. Mark the correct statements for abovementioned compoumds.(i) The above variation in acidities of the above acids are due to inductive effect only.(ii) The above variation are both due to inductibve and resonance effects.(iii) Inductive effect varies shrply with distance.

(iv) -I effect of chlorine is not much.(A) i and ii (B) i and ii (C) ii and iii (D) iii and iv

2.12 The correct order of acidic strength is :

(l)

COOH

OH(ll)

COOH

OHOH(lll)

COOH

CH3

COOH

CH3

OH

(lV)

(A) III> IV> I> II (B) II> I> III> IV (C)II> III> I> IV (D)II> I> IV> III

2.13 Which one of the following reaction is not possible?(A) CH3COONa + HCI CH3COOH + NaCI(B) CH3SO3 H + H C = C Na CH3SONa + H C = C H(C) R C = C H + PhONa PhOH + R C = C Na(D) H C = C H + NaH2 H C = C Na + NH3

2.14 IfS

O

P

OQR

H

CH3is mixed with NaOH solution. Acid base reaction occurs and HO snatches H from

organic molecule. Which carbon will loose H easily?

(A) P (B) Q (C) R (D) S

2.15 OH

COOH (x)OH

COOH (y)

(z) HOOC

HO

The correct acidic strength order of acidic hydrogen x,y and z is respectively.(A) x > z > y (B) x > y > z (C) z > y > x (D) y > z > x

2.16 H

N(p)

NH(r)

N

H

OO

(q)

The correct basicity order of atoms p,q and r is :(A) p > q > r (B) r > p > q (C) r > q > p (D) q > p > r


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2.17N

HI

N

H

II

O

N

H

III

N

IV

The order of basicity is(A) I > IV > II > III (B) I > II > IV > III(C) III > II > IV > I (D) II > III > IV > I

2.18 The correct basic strengtyh order is:

C

O

CH3

H2NC

O

CH2

NH2CH3

NH

ONH

C

O

CH3

I II III IV

(A) I > II > IV > III (B) IV > III > II > I(C) III > II > IV > I (D) III > IV > II > I

2.19 The correct order of acid and basic strength for the following pair of compounds should be?COOH COOH

CH3and

COOH COOHCH3

andAcid strength :

(I) (II) (III) (IV)

;

Basic strength :

NH2 NH2CH3

and

NH2 NH2CH3

and

(V) (VI) (VII) (VIII)

;

(A) I > II ; III > IV ; V > VI ; VII < VIII(B) I < II ; III > IV ; V < VI ; VII > VIII(C) I > II ; III > IV ; V > VI ; VII > VIII(D) I < II ; III > IV ; V < VI ; VII < VIII

2.20 Observe the foolowing reaction :

COOH

+

COONa OH

NO2

+

O Na

NO2

+

OH

NO2

ONa

NO2

+ NaHCO3 + H CO32

ONa OH

+ H CO32 + NaHCO3


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Which of the following is the correct order of acid strength :

COOH

(A)

OH

NO2

OH

> > H CO >2 3

COOH

(B)

OH

NO2

OH

> > > H CO2 3

COOH

(C)

OH

NO2

OH

> >H CO2 3 >

COOH

(D)

OH

NO2

OH

> > H CO2 3>

2.21. Which of the following statement is CORRECT regarding the inductive effect?(A) electron-donating inductive effect (+ l effect) is generally more powerfull than electron-

withdrawing inductive effect (l effet t)(B) it implies the shifting of s electrons from more eletronegative atom to the lesser eletronegative

atom in a molecule.(C) it implies the shifting of r electrons from less electronegativbe atom to the more electronegative

atom in a molecule(D) it increases with increase in distance.

2.22 Which of the following statement regarding resonance is NOT correct?(A) the different resonating structures of a molecule have fixed arrangement of atomic nuclei.(B) the different resonbating strcutues differ in the arrangement of electrons.(C) the hybrid structure has equal contribution from all athe resonationg structures always.(D) None of the individual resonating structure explains all charcteristics of the molecule.

SECTION-II: MULTIPLE CORRECT ANSWER TYPE2.23 Which of the following statements would be incorrect about this compoud?

NO2

NO2

NO2

Br

1 5

3

(A) All three C N bond are of same length(B) C1 N and C3 N bonds are of same length but longer than C 3 N bond(C) C1 N and C5 N bonds are of same length but longer than C 3 N bond

(D) C1 N and C3 N bonds are of different length but both are longer than C5 N bond

2.24 Choose the incorrect statement:(A) Salicylic acid (oHydroxybenzoic acid) is much stronger than its m-,p-isomers and benzoic

acid itself.(B) Acidity of salicylic acid is due to steric inbibition of re3sonance, as OH group forces

COOH out of the plane of ring(C) The orbitals which are in the same plane take part in resonance(D) All the resonating structures have real existence

2.25 In which of the following pairs the first one is the stronger base than second.

(A) CH3CHOO, HCOO (B) HO,NH(C) CH2=CH: , H C = C (D) CH3NH2, CH3,OH


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2.26 Which statement among the followijng are corect?(A) Hydration effect stabilises dimethyl ammonium ion more than trimethyl ammonium ion(B) In chlorobenzene as there is no hydration effect so, trimethyl ammonium ion gets less

stabillised than dimethyl ammonium ion(C) RCONH2 is feebly acidic with respect to RCOOH

(D) CH3> NH2> OH is the basicityh order

2.27 Resonance structures of a molecule should have.(A) Identical arrangement of atoms (B) Nearly the same energy content(C) The same number of paired electrons (D) Identical bonding

SECTION-III : ASSERTION AND REASON TYPE

2.28 Statement-1:Ortho iodobenzoic acid is strongest acid among all ortho halobenzoic acids.Statement-2: Iodine exerts maximum ortho effect (steric effect) so the acid weakening resonaceeffect of aromatic romg os decreased/(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True

2.29 Statement-1:Salicylic acid is much stronger than its m-, p-isomers adnsf benzoic acid itself.Statement-2:It is due to steric inhibition of resonance, as OH group forces COOH out ofthe plane of ringt.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1

(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True

SECTION - IV : TURE AND FALSE TYPE

2.30 Give the correct order of initials T or F following statements. Use T if statement is true and Fif it is false .S1 : Both the C O bond lengths in HCOOK are equalsNH2both have same dipole moment value.

S2 : HO OH NH2 NH2and

S3: Propyl chloride shows maximum dipolemoment in anti conformer.

S4 :N

N

NH2

is stronger base then

(A) T T T T (B) T F T F (C) T T F F (D) F F T T

SECTION - V : COMPREHENSION TYPE

comprehension # 1

The concept of resonance explains various properties of compounds. The molecules withconjugated system of p bons, are stabilized by resonace and have low heat of hydrogenation.


17/107

Hyperconjugative stabilization also decreases heat of hydrogenation. In aromatic rings a functionalgroup with a lone pair of electron exerts +m effect. Some functional groups like NO, NC,CH= CH2 can function both as electron releasing (+m, +R) or electron withdrawing (m, R)groups. More extended conjugation provides more stabilization.

2.31 The correct heat of hydrogenation order is(p) 1,3-Pentadiene (q) 1,3-Butadiene(r) 2,3-Dimethyl-1, 3-butadiene (s) Propadiene(A) p > q > r > s (B) s > q > p > r (C) q > s > p > r (D) s > q > p > r

2.32 The most stable carbocation is

(A)

(C)

(B)

(D)

2.33 The most stable resonating structure of following compound is O = N N = O

N = OO N(A)

N = OO = N(C)

N OO N(B)

N = OO N(D)

Comprehension # 2

The key concepts of resonance are :Resonance occurs because of the overlaping of orbitals. Double onds are made up of pi bonds,formed from the overlap of 2p orbitals. The electrons in these pi orbitals will be spread over mor4than two atoms, and hence are delocalized . Both paired and unshared electrons may bedelocalized , but all the electrons must be conjugated in a pi system. If the orbitals do not overlap(such as in orthogonal orbitals) the sturctures are not true resonance structures and do not mix.Molecles or species with resonance structures are generally considered to be more stable thanthose without them. The delocalization of the electrons lower the orbital energies, imparting thisthis stability. The resonhance in benzene gives rise to the property of aromaticity . The gain instability is called the resonance energy. All resonance structures for the same molecute musthave the same sigma framework (sigma bond form from the "head on' overlap of hybridizedorbitals). furthermore, they must be correct Lewis structures with the same number ofelectrons(and consquent charge) as well as the same number of unpaired electrons.Resonancestructures with arbitrary separation of chargfe of charge are unimportant, as arethose with fewer covalent bonds . theese unimportant resonance structures only contributeminimum (or not at all) to the overall. From the above theory of resonance answer the followings.

2.34 The correct resonation structre of 1, 3-butakiene is -

(A) CH CH CH = CH2 2

(C) CH CH = CH CH2 2

+

+

(B) CH CH CH = CH2 2

(D) None of these

+


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2.35 The correct stable resonating structure of benzene is -

(B)

(A) +

+

(C)

+

+

+ (D) None of these

2.36 Which resonating sturcture is not correct

CH =CHCH2 2(A) CH CH = CH2 2++

(C) CH CNH3 CH C=NH3

O O

NH CNH2 2

+NH2

NH C = NH2 2

NH2

(B)

(D)

N

H

N

H

+

SECTION - VI : MATRIX - MATCH TYPE

2.37 Match the following

(A)

CH3

CH3

CH3

CH3N

(B)

Cl

Cl

O

N=O+

O N2

(C)

CH3

CH3

NH2O N2

(C)

CH3

CH3

NO N2CH3

CH3

(p) is more

(q) is less

(r) Larger C N compared to C NO2

(s) Larger C N bond largteer compared to aniline


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2.38 Match the pKavalues with the given compoundsAcid pK a

NO2

OH

NO2

NO2

(A)

(B)CH COOH3

(C)

O

O

NH

Phthalimide

COOH

(D)

(p) 4

(q) 9

(r) 5

(s) 0.74

SECTION - VII : SUBJECTIVE ANSWER TYPE

SHORT SUBJECTIVE :

2.39 For the compound :

OH

Give the number 1 for presence of resonance only, 2 for presence of resonance andhyperconjugation only, 3 for presence of resonance, hyperconjugation and inductive effect and4 for presence of resonance hyperconjugation, inductive effect and electromaric efffect.

2.40

OH

CHCH

2

Br

Br

OHC

HOOC

x mole NH2

value of X used for complition of reaction will be :

2.41 Incorrect statement among these four :(i) I effect is prermanent polarisation of sigma bond pair of electrons in the molecule.(ii) In resonation structures the hybridisation of atoms do not change.(iii) In Hyperconjugative structures the hybridisation of carbon atom change.(iv) Presence of methyl group on an anion always destabilises ith anion.

2.42 Maximum number of hyperconjugtation forms of structure :


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2.43 In the following set of resonationg structures which sets have the second resonation structuremore contributing than first :

NH2

OCH3+

NH2

OCH3

+

N

O+

N

O

O OOO

+ClCl

N

O

N

O

I :

II :

III :

IV :


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3.1 Read the following road map carefully

CH3PhCH2CHOK + gas

EtOTsII

CH3PhCH2CHOTs

IV C H52 OK

CH3

PhCH2CHOH

K I III TsCl1-Phenyl-2-propanol

S.R = +33.02

CH3

PhCH2CHOC H2 5ethyl1phenyl2propylether

CH3

PhCH2CHOC H2 5Ethyl1phenyl2propylether

(A) Both the ethers obtained by the two routes have opposite but equal optical rotation.(B) One of the ether is obtained as a recemic mixture.(C) Step II & III both are SN2 reaction and both have inversion.

(D) Step II has inversion but step III has retention.

3.2 A compond A has the molecular formula C5H9CI. It does not react with bromine in crabontetrachloride. On treatement with strong base it produces a single compound B. B shas amolecular formula C5H8 and reacts with bromine in carbon tetrachloride. ozonolysis of B producesa compound cC which has a molecular formula C5H8O2. Which of the following structures isthat of A?

(A)Cl

(B)

Cl

CH3

(C)

Cl

CH3 (D)

Cl

3.3 2 4Me SONaOH

PhOH P, P is

(A) PhOSO2OMe (B) PhOMe (C) PhOSO2OPh (D) PhMe

3.4

P =Br

COCH COCH2 3

HD

NaOHP

Reaction Mechanism3


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Which of the following statement is correct

P = C CH3

O

O

HD

(B)P =OH

COCH COCH2 3

D

(A)

H

P =

O

D

(D)

H

P =(C) CH3

O

O

DH

3.5

OH

Br

NaOH

(B)

O

(C)

OH

OH

(D)O

(A)

OH

OH

3.6CH CH SH3 2

(i) CH O3(ii) ethylene oxide(iii) H O2

Product, Product is :

(A) CH CH S CH 3 2 2 CH OH2

( ) CH CH CH C O3 2 2 CH OH2 ( ) CH CH D S3 2

( ) CH CHB O3 2

CH2

CH2

3.7 Br

Ph + Ph CH NH2 2

O

EtOProduct, Product is

(A)

OEt

Ph

O

(B) Ph

O

NH Ph

(D) Ph NH Ph(C)

Br

Ph

OH

NH Ph

3.8 In the reaction A.

OHOH

CH3

CH3conc. H SO2 4

The product is -


23/107


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3.11 The products of hydrolysis ofO C H2 5O

, isH O3

(A) HOCH2CH2CH2CH2 CHO + CH3CHO (B) HOCH2CH2CH2CH2OH + CH3CHO(C) HOCH2CH2CH2CH2CHO + C2H5OH (D) HOCH2CH2CH2CH2CH2OH + C2H5OH

3.12

CH OH2

A.H SO2 4/H The product A is :

CH HSO2 4 CH2 CH2CH2

(A) (B) (C) (D)

OH

3.13 (CH3)3CCI + (CH3)3COK+

Product(A) SN Product will be more (B) E2Product will be more(C) both will be same (D) None of these

3.14 Neopentyl iodide is treated with aq. AgNO3solution, a yellow precipitate is formed along withother compound which is

(A) (CH ) CCH ONO3 2 23 (B) (CH ) C CH CH3 2 2 3

OH

(C) (CH ) CCH OH3 3 2 (D) (CH ) CCH CH3 2 2 3

ONO2

3.15 The major end product of the following reaction is

OH

CH Cl2

H C3

aq. AgNO3

OHH C3

C OHH2

(A)

CH3

H3C

O(B) (C)H3C O (D)

CH3

O

3.16 The major product P of the following reaction is

NH2 CH3

CH CH = C

CH3

NH2(D)

NH2 CH3

CH CH CH

CH3

NH2(C)

OCH3

NH2 CH3

CH CH C2

CH3

OCH3

NH2(B)

NH2 CH3

C CH CH2

CH3

NH2(A)

OCH3

NH2 CH3

CH CH CH

CH3

NH2

Cl

CH OH3 (P)


25/107

3.17 The product of following reacting is

14

Ar

O

OH

(A)

14

ArO

O

H O3

14

OH

(C) + ArOH

O

14 + ArOH

OH

O

(B)

14

O

(D) + ArOH

O

3.18

O

CH2H2C14 H /H O

+ 182

Which can not be the product.

H C214

CH2

18OHOH

(A)

CH214

CH2

18OH OH

(B)

CH2 CH2

18OH

(C)18

OH(D) A and B both

3.19 The correct order of SN2 \ E2 ration for the % yield of product of the following halide is -

CH CH C CH3 3

Ph

I

CH CH CH CH3 3

IPh

CH CH 3 I2 CH CH CH CH3 3(P) (Q) (R) (S)

I

(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S

3.20 The poduct in the given reaction is

H ONa +

Me

Ph

H Me

Ph

Br

I II

P

H O

Me

Ph

Me

Ph

H

(A)

H O

Ph

Me

Me

H

(C)

Ph

H O

Me

Ph Me

Ph

H

(B)

H O

Me

Ph H

Me

Ph

(B)


26/107

3.21

Ph

reaction Rearranged most stable Carbocation is

Ph Ph PhPh

(A) (B) (C) (D)

3.22 H Br

Ag+Rearranged Carbocation + AgBr

Rearranged carbocation is :

+(D)(C)(B)(A)

CH3

SECTION - II : MULTIPLE CORRECT ANSWER TYPE

3.23 The correct statement(s) about solvent effect is\are :(A) Decreasing solvent polarty causes a large increase in therate of the SN2attack by ammonia

on an alkyl halide

RX + NH3 RNH3 + X+

(B) Increasing solvent polarity causes a large decrease in the rate of the SN2attack by hydroxideion on trimethyl sulphonmium ion

HO (C+ H3 3) S CH OH + (CH ) S3 3 3

DMSTrimethylsulphonium

ion

(C) Increasing solvent polarty causes a small decrease in the rat3e of the SN2 attack bytrimethylamins on trimethylsulfonium ion.

(CH ) N (C3 3 3+ H ) S3 CH N(CH ) + (CH ) S3 3 3 3 2+ +

(D) all ar3e incorrect

3.24 Which of the following reaction(s) is\are posible

(A) CH C ClCH NEt3 2 2H CH C (NEt )CH OH3 2 2HOH

(B) Either CH C3 H C H SEt or CH CH(sEt)CH OH2 3 2 CH C ClCH3 2H SEtHCl

OH

(C) Treatment of either epoxide I or epoxide II with aqueous OHgives the same product III

CH CH CH CH Br3 2 CH CH CH CH3 2or

O BrI II III

O

CH CH CH CH3 2 OH

O

OH


27/107

(D)

OH

OEt

OH

OEt

+

OH

OEtEtOH

EtO

3.25OH

OH

NaOH

1eq P Q R 'S'O

CH CCl2

Cl

NaOH LiAlH4

O

O

O

R =(A)

O

Q =

OH

C = O

CH Cl2(C)

Q =OH

CH C Cl2

O(B)

S =

OH

OH

OH(D)

3.26OH

NH2

CH3C H6 4Ph

H

Ph

?HNO2

H

Ph

O

Ph

pCH C3 6 5H O Ph

HPh

pCH C3 6 5H

(A) (B)

H

Ph

O

Ph

pCH C3 6 5H (C)Ph O

HPh

pCH C3 6 5H

(D)

3.27 Which of the following reaction will go faster if the concentration of the nucleophile is increased?

H Br

+ CH O3

(CH ) CCl3 3 CH COOH3

H O2

+ CH S3

Br

Br Acetone

KI

(A) (B)

SECTION - III : ASSERTION AND REASON TYPE

3.28 Statement-1 : (CH ) C CH3 3

OH

CH3

(CH ) CCH=CH +3 3 2 CH3

CH3

CH3

CH3C=C + CH2=C

CH3

CH(CH3)2

H SO2 4

40% 20% 40%

Statement-2 :It follows Hofmann's elimination by E2.


28/107

(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


3.29 Statement-1 : Ethers are prepared from alcohols in acid medium through SN1or SN

2mechanismsdepending upon nature of alcohol.

Statement-2 : ROH + H+ R OH2+

R O

H

R OH2+

R O R + H O2 ROR + H O3+

slow +

H

or, R OH + H+

R R + H O+

2OH2+

R + O R R O R+ +

slow

H H

R OR + H O3+H O2

fast



SECTION - IV : TRUE AND FALSE TYPE

3.30Ph

OH

CH3 PhCH3 (Elimination follows E mechanism.)1H SO2 4

Heat


Comprehension # 1

Read the following reaction

O

H+P

Cl2

hQ R S T

NaOEt / NBS NaOH

3.31 Compound 'T' is

OH

OH

OH

OH

OH

HO

OH

OH

(A) (B) (C) (D)


29/107

3.32 Compound 'Q' is

OlOH

Cl

OH

Cl

OH

Cl

(A) (B) (C) (D)

3.33 When treation 'S' with strong base, product obtained is

OH OH OHOH

Br

Comprehension # 2A hydrocarbon (X) of the formula C6H12 does not react with bromine water but reacts withbromine in presence of light, forming compound (Y) . Compound (Y) on treatment with A|c. KOHgives compound [Z] which on ozonolysos gives (T) of the formula C6H10O2. compound (Treduces Tollens reagent and gives compound (W).(W) gives iodoform t4st and produce compound(U) which when heated with P2O5 forms a cyclic anhydride (V).

3.34 Compound V isO

O

O

CH3

O

O

O

CH C CH 3 2 CH CH = O2

O

(A) (B)

(C) (D) CHO CH = CH CHO

3.35 Compound W is

(A) COOH (CH ) COOH2 2 (B)COOH

COOH

(C)COOH

COCH3(D) CH CH CH COOH3 2

CH = O

3.36 Compound 'X' is

(A)

(C)

(B)

(D)

CH3CH3

CH3

CH3 CH3


30/107


3.37 Match the column I with column II

CH3H

ClPh

C = CKNH2

CH3

OH

Ph

HSOCl2

CH3N

CH3

CH3

C

O

Ph +NaOH

CH CH CH2 2 3

CH NCH CH3 2 3CH3

CH2CH3

+ NaOH

(P) -elimination

(Q) SN2

(R) -elimination

(S) SN1

(Y)

(Z)

(W)

(X)

Column - ( )

Reactions

I Column - ( )

Reactions

II

3.38

CH CH CH3 2 2

CH CH2 3

CBr + H O2

H C3

CH CH2 3

CBr + H O2

H C3

CH =CHC Cl + SH / (CH COCH2 3 3)

CH3

CH3

(A)

(B) CH CHDCl + OH3

(C)

(D)

(p) Retention

(q) Racemisation

(r) Inversion

(s) Product with -bond shift

Substrate Stereochemistry of product


31/107


SHORT SUBJECTIVE :

3.39 Correct statement about nucleophiles and leaving groups is/are

(i) Nucleoghiles have an unshared electron pair and can make use of theis to react with andelectron rich species.

(ii) The nucleophillicity of an element generally inhcreases on goiing left to right in periodictable.

(iii) A nucleophile is an electron deficient species(iv) Leaving group ability kincreased in moving from L R and T B in periodic table.

3.40CH CH3 CCH Br2

CH3CH3

CH3NaOH/H O2

Which of the following stat4ements is incorrect about the given reaction

(i) The reation is SN1 reaction(ii) The reaction intermediate is planar (sp2)(iii) The major product will be 2-ethyl-3-methylbutan-2-ol(iv) The major product has two stereogenic centre

3.41 which of the following will not give SN1reaction with aq. AgNO3.

(i) (ii)CH Br2

Br

Ph

PhBrPh

Ph

Br

(iii) (iv)

Br

3.42 In the given reaction following products are expected.

CH Br2CH3

+

CH2OCH3

CH3

OCH3

+ ++

OCH3

(I) (II) (III) (IV) (V)

CH OH3

Which observetions seen to be incorrect(i) Ist is the major product obtained by E1 reaction(ii) IV is the major product obtained by SN1 reaction(iii) formation of II or V involves a strained carbocation intermediate(iv) In the solvolysis reactions a carbocation intermediate is formed.

3.43 Observe the following flow chart and answer the number of x,y, z, w.

PositionalIsomers = (X)

MonochloridesIsopentane

TotalIsomers = (Y)

Total number of 1 alcohols = (Z)including stereoisomers

KOH/DMSO

(SN )2

X Y Z


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4.1 2-Phenylcycloprop-2-en-1-one is allowed to react with phenylmagnesium bromide and kthe reactionmixture is hydrolysed with prechloric acid. The product formed is

(A) Ph C C CHO

Ph

OHO

(B)

Ph

Ph

O

(C)OH

Ph

Ph

Ph

Ph

(D)

4.2 Which of the following reactions will give 2 chiral alcohol as one or more of major organicproducts?

(A)

H

D

CH3

MgIO2 H O3 (B) CH MgI3 + H C OCH

O

CH3

C H2 5H O3

(excess)

(C)

H

CH3

MgBr + CH2

O

CH2

H O3(D) None

4.3CH3 C C CH3

O O

PhMgBr

(excess)

H O2 No of product (X)Fractional distillation

no. of fractios (Y)

(A) 3,2 (B)3,3 (C) 4,2 (D) 4,3

4.4 The end product of following reaction is

O

O

OCH MgBr3 PhMgBr

(1) (2) (3)

H

(A) ,-diketone (B) -Hydroxy acid (C)1,2-Diol (D) -Hydroxy acid

4.5 Observe the following reaction sequence

X Br / hv2 Y Mg / Ether Z

O

Wdil.H SO2 4 U

O /Zn/H O3 2 O

X can be

(A) (B) (C) (D)CH3

Grignard Reagent

Reduction & Alkane4


33/107

4.6

O(x) CH OH2

pyridine,

SOCl2 Mg

(C H ) O2 5 2 H+

O

CH C(CH )2 3 2

Product

Product of the reaction is

CH C CH CH2 2 3

OH

CH3

O CH C CH2 2H C( )3O

O

CH C H2 H C O2 O

CH3

CH3

CH C H2 C OH2O

CH3

CH3

(A) (B)

(D)(C)

4.7 Observe the following sequence of reactions.

CH CH CH3 2 3 (X) (Y)(1)Br / hv2

(2)

Mg/ether

(3)

CH Br3(4)

Cl / hv2

(5)

CH OH3(Z) (W) (R)

The product R is :

(A) CH CH 3 CH OCH (B) CH CH CH CH OH (C) CH CCH (D) CH C CH2 3 3 2 2 2 3 3 3 3

CH3 CH3 CH3

OHOCH3

4.8Ph N = C = O

(i) CH MgBr3(i ) Hi O2

LiAlH4P Q

(A) P is PhNHC CH and Q is PhNHCH CH3 2 3

( ) P is Ph NH CH and Q is HB N3 3

O

( ) P isC PhN=C OH and Q is Ph NH CH3

CH3

( ) P isD Ph NH CH and Q is Ph NH C CH3CH H 3

CH3OH3

4.9 Which of the following reduction methods is not suitable for preparing and alcohol?

(A) CH COOC H +3 2 5 NaBH4

( )C CH C O3 H C Cl+2 LiAlB4

( )B CH COOC H +3 2 5 Na/EtoH

( ) CH COO HD H +3 2Ni

4.10 C C C C

Ph CH

Br H

C = CH

CH Ph

Br

Li / NH3 Br2 (1equivalent)X,

'X' is :

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


34/107

4.11 Compound

OO

O

N

C

ClO

on reduction with LiAIH4produces

HON

CH OH2

CH OH2

CH OH2

(A)

HOO

OH

N

CH OH2

(B)O

OH

N

CH OH2

(C)N

CH OH2

CH OH2

CH OH2(D)

4.12 Which one is the correct energy profile for CI reaction ?

(A)

R.coord

Energy

(B)

R.coord

Energy

(C)

R.coord

Energy

(D) All of these

4.13 Which of the following is correct statement regarding relative acidic charcter of cyuclopropaneand propane ?(A) Cyclopropane is more acidic than propane(B) Propane is more acidic than cyclopropane(C) Both are equclly acidic(D) Bothe are neutral

4.14

No . of products and No. of fractions are respectively

(A) 6,5 (B) 6,4 (C) 5,4 (D) 6,3

4.15 Which of the following is correct potential energy diagram for the given chin propagatiog step.

CH H+F3B.E.=435kJ/mol

CH + H F3B.E.=569kJ/mol

= 32 kcal/mol


35/107

4.16 Consider the following reaction

CH CH3 CHCH + Br3

D CH3

'X' + HBr, X can be

CH CH3 CHCH2

CH3D

CH CH3 CCH3

CH3D

CH C3 CHCH3

CH3D

CH CH3 CHCH3

CH3

(A) (B) (C) (D)


4.17 Br

Mg NBSBA C D E + F

Zn

AgNO / H O3 2 O / H O3 214

(i) CH COCH3 3(ii) H(iii)

(A) Product C is

Br14

(A) Product D is

OH14 OHOOH

O 14

&only (D) F is

(B) E is CH = O & CH = O2 214

4.18

Ph CH CH CH2 3

CH3

(monochlorination)

Cl2 / h

Which statements is /are correct about photochemical chlorination of theabove compound [Morethan one correct](A) The major product wil be chiral carbon atom having optically inactive compound(B) The intermediate free radical of the major product is resonance stabilised(C) The intermediate free radical is tertiary(D) THe intermediate free redical is planer , and stabilised by only hyperconjugation

4.19 Which reaction is/are correct.

(A)C N

tertiary alcohol(i) Mg / Ether

(ii) H O3

(B)

Cl COOH

Mg

ether

CO2 H O3+

F

Cl

MgF

MgCl

Mg

ether(C)

(D) + CH C3

O

CH CH MgBr3

HO C C CH3

H O3

+

+


36/107

4.20 Point out the following incorrect Grignard synthesis.

N

H

Br

N

H

CH Ph

OH

(i) Mg, ether

(ii) Ph CH = O

(iii) H O3

Br

OO

HOCH2

OO

MgBr(C) OH

(B)

(A)

(i) Mg, ether

(ii) PhCH = O

(iii) H O3

OH

(D)

O CH CH2 3HO

OH

(i) CH C CH3 3

(i i) H O3

O

(i) CH CH MgBr (1eq.)3 2

(i i) H O3


4.21 Stetement-1 :Cyclopropane has the highest heat of combustion per methylene group.Statement-2 :Its potential energy is raised by angle strain.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1.(C) Satement-1 is True, Statement-2 is False.

(D) Statement-1 is False, Statement-2 is True.

4.22 Statement-1 :Branched alkanes have lower boiling point than their unbranched isomers.Statement-2 :Branched alkanes has relatively small surface area, so less London's dispersionforce act among molecules.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


4.23 Statement-1: Alkanes float on the surface of waterStatement-2 :Density of alkanes is in the ranbe of 0.6 0.9 g/ml, which is lower than water.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


4.24 Statement-1 :Grignard reagent can be prepared in all nonpolar solvent.Statement-2 :Diethyl ether solvates the Grignard reagent.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for



37/107

4.25 Statement-1 : The preparation of G.R. occurs in solution phase.Statement-2 :Teh reaction will be explosive in solid phase. GR. is stable only in solution phase.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for

Statement-1

(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True


4.26 Observe the following natural product and choose the correct statement

(x)HOOC

COOCH3

C H56

N (w)H

(y) O N2O(z)

O(r)

(1) LiAIH4will reduced x, y, z, w, r(2) NaBH4will reduced r(3) Na/C2H5OH will reduced r, w(4) (CH3)2CHOH + [(CH3)2CHO]3AI, (MPV) will reduced r(A) TFTF (B) TTTT (C) FTFT (D) FFFT

4.27 Diethyl ether is the solvent for Griganrd reagent but not for RLi, because RLi reacts withC2H5OC2H5 and givesw CH2 = CH2.


Comprehension # 1

Read teh following reaction

CH CH P QMg

Ether

NaOClR S

Cl

2CH CHO2

KOH NaOHH O2

T(ii) Dil.KMnO4

(i) H / Pd. BaSO2 4

4.28 'S' in the above reaction

(A) CC

CH2O

H

CH2

OH

(B) C

C

CH2O

H

MgBr

(C)

C

CMgBr

CH2OH

OHH(D)

C

C

OHH

CH2 OH

HHO

CH2 OH

4.29 'U' is

H OH

H

H

H

OH

OH

OH

CH OH2

CH OH2

(A)

H OH

H

H

H

OH

HO

HO

CH OH2

CH OH2

(B)

H OHHO

OH

OH

H

H

H

CH OH2

CH OH2

(B) OHH

COOH

CH OH2

(D)


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4.30 'Q' is(A) CIMgC CMgCI (B) CH C MgCI(C) CIOC CMGCI (D) CIOC COCI

Comprehension # 2

considering the following reations(I,II,III)and give your answer for following questions

HO CCl

O

(i) CH MgBr3

(ii) H O3+

COEt

O

(i) CH MgBr (excess)3

(ii) H O3+

CH Cl2

EtO C OEt

O

(i) Ph MgBr (excess)

(ii) H+

(a)

EtO C OEt

O(i) CH MgBr (excess)3

(ii) H+

(b)

H C OEt

O(i) Ph MgBr (excess)

(ii) H+(c)

H C OEt

O(i) CH MgBr (excess)3

(ii) H+

(d)

ClCH COOEt2

(i) CH MgBr (excess)3

(ii) H+

(e)

4.31 If CH3MgBr is taken in excess in reaction (I), how many moles of CH3MgBr will be consumedin reaction (I)

(A) 2 (B) 3 (C) 4 (D) 5

4.32 The product in the reaction (II) will be

CCH3

O

Cl

CCH3

Cl

OEt

OH

CH C CH3 3

OH

CH2Cl

CH C CH3 3

OH

CH2 CH3

(A) (B) (C) (D)

4.33 In which seft of the reactions in (III) the product will be 2 alcohol ?

(A) a, b, c (B) b,c,d (C) c,d (D) c,d,e


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4.34 Match teh following consider the reaction of CH3MgBr with the compounds in column A andproduct are written in column B.

Column A Column B

(A) CINH2 (p) CH3CN

(B) CICN (q) CH3NH2(C) CH3COCI (r) C2H5COCH3(D) C2H5COOC2H5 (s) CH3COCH3

4.35 Match the following :

O

Cl C

O

C

COOH

O C CH3

CH = CH2

O

(i) [Al(OiPr) ] + CH CH CH3 3 3(ii) H O2 OH

(1)

(2)

(P)

(Q)

NaBH (C H OH + H O)4 2 5 2

Na/EtOH (low temp.)(3) (4) (ii) H O2

(R)(i) LiAlH / Et O4 2

(S)

H C OH

COOH

HOH C2

O

O C CH3

CH = CH2

HC

OH

COOH

Cl C

O

O C CH3

CH = CH2

O

HC

OH

COOH

HOH C2

O

O C CH3

CH = CH2

O

HC

OH

COOH

HOH C2

OH

CH = CH2

O

(X)(P)

(Y)

(Z)

(Q)

(R)

(W)(S)

Column - I Column - II


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4.36 Match the following :Column A Column B

(A) CH3CHCI 3 2Li CH CH CI

Cul? (p) (CH3)2CHCH2CH(CH3)2

(B) (CH3)2CHI 3 2Li (CH )CH Br

Cul ? (q) CH3CH2CH2CH3

(C) CH3CH2C(CH3)2Br 3 2Li CH CH Br

Cul(r) (CH3)3CCH2CH3

(D) (CH3)3CI 3 2Li CH CH Br

Cul(s) CH3CH2C(CH3)2CH2CH3

4.37 Match the following :Process Graph

(A) Fluorination (p)

Potentialenergy

Reaction CO-ordination

A

B

C

(B) Chlorination (q)A B

C

(C) Bromination (r)A

B

C

(D) Iodination (s)

A

B

C

Position(A) is for CH4,X, (B) is for CH3, HX, (C) is for CH3X,X


SHORT SUBJECTIVE :

4.38 An isomer of C5H12 gives total six isomeric products on monkochlorination. Calculate thepercentage yield of the primary monochloride which is chiral. Consider the following relativereactivity of CH bonds for chlorination.

1 3 5

2 C H 3 C H1 C HDegree of C H

Relative reactivityfor chlorination (RR)


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4.39 How many molar equivalent of R-MgX is required in reaciton with formic anhydride completely?

4.40

HS

C NH2 C CH

O

C OH

O

excessCH MgBr3 the numbers of CH gas formed in this reaction4

4.41 Observe the following experiment

Mgpowder

An alkyl halide (P)ethereal solution

(lce)

A sweetsmelling liquid (Q)

H O2

(R)(1) (2)

(I)(II) (III)

(a) If the reactant 'P' is ethl chloride then the product R has the numbers of optically activecompound:

(b) If the loquid Q isH C OC H2 5

O then the product R can be (P can be any other halide)

CH CH CH3 3

OH

(1) CH C CH3 3

OH

(2)CH3

H C C H52

OH

(3)H

C H C C H2 5 2 5

OH

(4)C H2 5

(c) If R is C CH3

CH3

OH

then the numbers of monochlorination product are:

4.42 O

O

O

1 mole CH Mg X3

+ H O2X

The numbers of stereoisomers of 'X' is :


42/107


5.1 The major product of the following reaction would be

NH

Br2

NH

BrBr

N

H Br

N

H Br

N

Br

(A) (B) (C) (D)

5.2 In the following series of reactions the major products P and S are respectively.

Br2 / h (P)tBuO ,

(Q)(i) HOBr/H+

(ii) ThO2,

(iii) alc.KOH,

(R)(i) HOBr/H+

(ii) ThO2,

(iii) alc.KOH,

(S)

(A)Br

;

(C)

Br

;

(B)

Br

;

(D) ;Br

5.3 End product D of the following reaction will be

ClA B C D

H O2 ZnCl HCl2 Mg/ether D O2

D(A) (B) OD (C) D (D) D

OD

5.4 consider the following reactions

H C5 2 C2H5

H

C2H5

HC = C

H C5 2 H

HC = C

C2H5CH2CH C5 2

O2CH

3

CH2

COOH

R1 R2

R3

R4

H C C5 2 CC H2 5

The correct set of reagents for these reactions is

Alkenes & Alkynes

5


43/107

R(A) H /Lindlar catalyst(B) H /Lindlar catalyst(C) (i) O , (ii) H O(D) H O,H SO ,HgSO

1

2

2

3 2

2 2 4 4

RNa / Iiq.NHNa / liq.NHH O,H SO ,HgSOH /Lindlar catalyst

2

3

3

2 2 4 4

2

R(i) O , (ii) H OH O,H SO ,HgSONa / Iiq.NH(i) O , (ii) H O

3

3 2

2 2 4 4

3

3 2

RH O,H SO ,HgSO(I) O , (ii) H OH /Lindlar catalystNa / Iiq.NH

4

2 2 4 4

3 2

2

3

5.5 The major product of the following reaction is :

Br Cl(1)

Na / ether

(2)

Br2 / h C H O2 5 / C H OH,2 5(3)

(A) (B) (C) (D)

5.6 Themost ap0propriatew major product of the followning sequence of reactions would be.

CH CH3 2

H3C

C C

CH3

H

CH C O O H3

O

LiAlD4 H3+

O

Me

Me

D

OH()

Et

H(A)

Me

CH3

DH

H()

Et

D(B)

Me

Me

OH

D()

Et

H(C)

CH3

CH3

DH

OD

CH CH3 2

H(D)

5.7 Compound'P' of the following reaction swequence can be

(P) [C H O ]8 6 3O O

O

H O2

+

COOH

[C H O]8 8 CH COOH2CrO / Acetone / H O3 2

[C H ]16 21B

HOO

BH

C C(A) CH2 C CH(B) C CH(C) (C) CH = CH2


44/107

5.8 The alkene limonene has the following structure,

Which product resutls from the reaction of limonene and 1 molar equivalent chlorine water?

OH

CI(A) OH

CI

(B)

OH

CICI

(C)HO

OH (D)CI

CI

5.9 The end product 'W' in the follownign sequence of reactions is :

CH CH2 3

NBS(X) W

alc. KOH

aq. KOH

Y

Z

Hg(OAc)2NaBH4

(A) Ph CH CH O CH Ph2 2

CH3

( ) Ph CH CH PhC 2 2O CH2

( ) Ph CH B O CH Ph

CH3CH3

(D)

Ph CH CH3

CH = CH2

5.10 Which of the following corrently represents tthe rate of acid-catalysed hydration of followningalkenes.

C = CH CH3

CH3

CH 2= CH C H5 PhCH = CH C H2 5 CH C = CH3 2

CH3

(l) (ll) (lll) (lV)

(A) lll > l > ll > IV (B) lV > lll > l > Il (C) l > lll> lll > IV (D) lV > lll > lll > I

5.11 PhC CPhHOCl/H

+Na/NH3

Ph

Ph

A B ; B is

H

Cl

OH

H

(A) (B)

Ph

Ph

HO

Cl

H

H

(C)

Ph

Ph

H

H

OH

Cl

(D) B and C both

5.12 The most stable conformation of the product of followning reaction

C CHHBr / R O2 2

(1 eqivalent)

HBr / dark

H

Br

Br

HH

Ph(A)

Ph

Br

Br

HH

H(B)

Ph

Br

Br

BrH

H(C)

H

H

H

BrPh

Br(D)


45/107

5.13 In the given reaction,

CH3

(X)

B H , THF2 6 H , NaOH2O2 TSCl tBuO K +

(Y)

The product 'Y' is(A) A positional isomer of X (B) Identical to X(C) Chain isomer of X (D) An oxidation product of X.

5.14 Which of the following compouinds would liberate two moles of methane when treated withmethyl magnesium bromide?

CH CH CH C CH3 2(A)

OH

CH C CH C CH3 3(C)

O

CH3

O

(B)

(D)

CH C CH 3 2 CH OH2

O

OH

COOC H2 5

5.15 The best yiest of product 'X' ca be obtained byt using which one of the foloowing sequence ofreagents and reactants

X = CH C C CH CH (CH )3 3 2

OH

(A) CH C CH3NaNH2 (CH ) CHCHO3 2 H3O

+

(A) CH C CH3NaNH2 (CH ) CHCHO3 2 H3O

+

( ) CH C CB ( 3) CH H C H2CH3I

NaNH2

( ) CH C CC 3 H HC H C C2 3CH3INaNH2

OH

OH

( ) CH C CD ( 3) CH H C H2

CH3ICH3MgI

OH

5.16

H C CH CH3 2 3C

CH3

H CH 3 2C NCH2

H C CH3 3C

CH3

CH3 C Cl

O

X, X isAlCl3

(i)CH 3I

(ii) AgOH,

In the above reaction the product will be


46/107

(A) CH CH CH Cl3 2

COCH3

( ) CH CH CH CB 3 2 CH3

Cl O

( ) CH CH CH C 3 2C CH3

Cl

( ) CH CH CH CB 3 2 CH3

Cl OO

CH3

5.17 Fastest rate of electrophilic addition will take place in

(A) HO CH = CH2

(C)CH3O CH = CH2

(B)ON CH = CH2

(D) CH = CH2

5.18 Which of the following will be the correct product (P) for the given reaction ?

OH

Conc. H PO3 4(P)

OH

(A)

OH

(B) (C) (D)

5.19 CH2 X (major)HBrR O2 2

aq NaOHY (major)

H2SO4/ Z (major)

Identify the correct option

BrCH3

BrCH3

OHCH3

OHCH3 CH3

CH3

CH2

OH

CH3Br

CH3

OH

CH2 CH3

Br

CH3

X Y Z

(A)

(B)

(C)

(D*)


47/107

5.20 X HOOC C CH CH CH CH COOH2 2 2 2

O(i) KMnO4 / H O2 /

(i i) H O3+

X may be

(A)COOH

(B)

COOH

(C)COOH

O

(D)

O

5.21

CH3CH3 CH3

CC = C

H(1) C H CO H6 5 3 ( )2 CH MgBr 3 ( )3 H O/H2

+

Product; Product is :

D CC H(CH ) C3 3 D

OHOH

(A) D CC H(CH ) C3 3 D

OH3OH3

(B) D CC H(CH ) C3 3 D

OH3OH

(C) D CC H(CH ) C3 3 D

OHOH3

(C)

5.22 The final product of the following reaction is

MeHH oCOCH3

Ph

Ph

BrCl/CCl4

BrMe

H Cl

Ph

Ph

(A) ClMe

H Br

Ph

Ph

(B) MeBr

H Cl

Ph

Ph

(C) MeBr

H Br

Ph

Ph

(D)


5.23 Which statement is correct about the end product of the following reaction series,

C CHHOCI (excess)

(1) (2)

conc. NaOH,

(A) It is optically inctive hydroxy detone (B) It is a resolvable hydroxy acid(C) It is a nonresolvable aldehyde (D) It is an optically inactive hydroxy acid

5.24 The following synthesis can not be carried out be:

CH = CH2 CH = CH2

I

CI I

(A)CI2(1) (2)

ICI / CH COOH3 ICI / CH COOH3(3)

Zn dust

(4)

(B)HOCI / H

(1) (2)

CI / Fe2(3)

ICI / ZnCI (excess)2

(4)

NaOH,


48/107

(C)

(B)

(1)

HOBr / H

(2)

CI / Fe2(3)

ICI / ZnCl (excess)2(4)

Zn dust, CH COOH3

Br / CH COOH2 3

(1) (2)

CI / Fe2

(3)

ICI / CH COOH (excess)3

(4)

NaNH2

5.25 Bu C CHLiNH2 A

(i) PhCHO

(ii) H O2

BMnO2 C

Compound C of the above reaction can not be :

(A)

CHO

C CBu(B)

CHO

C CBu(C)

CHO

C CBu

(D)

O

C C CBu

5.26 Acetone (CH3COCH3) is the major product in :

I

II

III

CH = C = CH2 2H O3

CH C CH3H SO / HgSO / H O2 4 4 2

CH C CH3BH THF3-

H O / OH2 2

(A) I (B) II (C) III (D) none


5.27 Statement-1 :

CH2

CH2

HBr

40CCH3

Br

CH2

MinorMajor

CH2+

CH2Br

MinorMajor 20C CH

3

Br

CH2 CH3+

CH2Br

Statement-2 :

CH2CH2 H

+

CH3

CH2+

Allyliccation

Br

Br

CH3 CH2

CH2CH3

+

Br

major at low tempmajor at of high temp

CH3

CH2

Br


49/107


Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.

5.28 Statement-1 : Me

MeNBS

Me

Me

Br

+

Me

MeBr

Statement-2 : Me

Me

Br.HBr

Me

Me

Me

Me

Br2

Br

Br2

Me

MeBrMe

Me



5.29 Statement-1 : Reduction of but-2-yne by Na/liq. NH3given 'trans' but-2-ene.Statement-2 :It is an example of 'anti' addition.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


5.30 Statement-1 : But-1-ene gives 2-Bromobutane with HBr/PreroxideStatement-2 : The reaction involves formation of more stable free radical and in that respect theaddition is Markovnikof although the product obtained appears as anti Markovbnidof product.




5.31 The addition of HBr to butadiene at 80C to give 1, 2-adduct is kinetically controlled while thatat 40C to give 1, 4-adduct is thermodynamically controlled.

5.32 In preparation of terminal alkynes from vicinal dihalides, at least 2 equivalents of sodium amide

must be added per mole of vicinal dihalide.


50/107


Comprehension # 1

Demercuration allows Mardownikoffs addtion of H, OH without re arangement. The net result isthe addition of H2O. Answer the following question.

5.33 CH3

CH3

CH3 CH2CH =C i)Hg(OAc) . THF2

ii)CH OH, NaBH NaOH3 4A

HI (Conc.)B, Product B is :

(A) (CH ) CCH CH3 3 3

OH

(B) CH3I (C) CH CH3 2I (D) (CH ) CCH CH3 3 3

I

5.34

CH CH = CH3 2

O

NBr

OA

1) Hg)OAc) , THF2) H O

2

2

3) NaBH , NaOH4B C.

OH

The product 'C' formation from B occurs throuth(A) enol formation (B) SN

1mechanism(C) Neighbouring group particitation (D) SNAR mechanism

5.35

OHi) Hg(OAC) .THF2

ii) NaBH , NaOH4A,

Product 'A' is :

(A)

OH

HO (B) OH (C)

OH

(D)

OH

OH

Comprehension # 2

(A)AI O2 3

250C(B)

HI

(ii) AgOH(C)

AI O2 3

150C(B) (A)

(i) B H2 6

(ii) H O ,OH2 2

In the above reaction sequence (A) and (c)are isomers. MOlecular formula of B is C5H10, which

can also be obtained from the product of the reaction with CH3CH2MgBr and (CH3) CO andfollowed followed by acidification.

5.36 Identify the structure of A(A) CH3CH2CH2CHCH3(B) (CH3)2CHCHOHCH3(C) (CH3)3CCH2OH (D) CH3CH2CHCH2CH3

OH

OH

5.37 Identify th structure of B

(A) (CH ) CHCH=CH3 2 2 (B)

CH3

CH2

CH3

CH3 C C=

(C)(CH ) CH= CHCH3 2 3 (D) CH =CHCHCH2 3CH3


51/107

5.38 Identify the structure of C

OH OHOH

CH3

(A) CH CH CH CHCH (B) CH CH CCH (C) (CH ) CCH OH (D) CH CH CHCH CH3 2 2 3 3 2 3 3 3 2 3 2 2 3

SECTION - VI : MATRUX - MATCH TYPE

5.39 Match the column Iwith column II

Column -(I) Column -(II)

(A) C CDHgSO4

D SO , D O2 4 2

(B)

CH3

*14 H SO2 4

H O2

(C)

CH3

*14 B H /THF2 6

OH /H O2 2

(D) C CDB D /THF2 6

OD /H O2 2

(p)

CH3

OH

CH3

*14

(q)

CH3

CH OH2

*14

H

(r) CD CDO2

(s) C CD3

O


SHORT SUBJECTIVE :

5.40 (a) CH3 CH3

OH OH(X)

CH C C CH

Total no. of stereoisomers of the product when above compound(b) Total no. of stereoisomers of the product when above compound (X) is reduced by lindlar

catalyst.(c) Total no. of stereoisomers of the product when (X) is reduced by Na/liq NH3(Birch reduction)(d) No. of products that we wil kjget when optically inctive form formed in part (B) reacts with

PhCOOH followed by hydrolysis.

5.41 CH3 CH = CH CH3 reacts with Cl2at 500C. Find out total no. of possible products.


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5.42

Et

CHCIBr2

(CH )3 3 COKm no. of products.

5.43CH3 CH3

CH

CH

+ CH N2 2U m Total no. of products.

5.44

CH3 Cold Dil

KMnO4

KMnO4HIO4

NH OH2

(excess) Total no. of isomers (including stereo) are formed in

the products.


53/107

SECTION-I : STRAIGHT OBJECTIVE TYPE

6.1

CH = CH COOH

HOCI / H

The major product is :

(A)

CH = CH COOH

CI

(B)

CH = CH COOH

CI(C)

CH = CH COOH

CI(D)

CH CH COOH

CI

OH

6.2 MeO OH CI

O

O

S MeHCI(1)

Br / Fe

(2)2 H

(3)

+

The major product is

(A) MeO

Br

(B) MeO

Br

OH (C) MeO

Br

(D) MeO

Br

OH

6.3 The product is :

OHO

O

O

||

||

product.

O

O

OH

OH

(A) (B)

O O

O

O O

(C)

O

O

OO

(D) None

6.4

Ph

Me

Me

OH

PhC C

I

AgNO3

Aromatic Compounds

6


54/107

Major product is

(A)Ph

NO3OH

MeC C

PhCH3

(B) Ph

Me

C

Ph

C

O

Me (C) Ph C C Me

PhO

Me

(D) None of these

6.5

CH3

Me CCI3

AICI3

PhCOCI

AICI3

Br / AICI2 3Product is

(A)

Me O

C Ph

(B)

Me O

C PhBr

C(Me)3

(C)

Me O

C Ph

Br

(D)

Me O

C Ph

Br

C(Me)3

6.6 Why does the reaction produce stable salt?

OHCI

A

OHCI+

Because(A) In 'A' the ring is aromatic(B) 6 p electrons are present(C) Ring in a is stabilised by closed loop conjugation(D) All of these

6.7 The major product of reaction

O

C

OMe

O

HNO + H SO3 2 4

O

C O

(A)

NO2

OMe

(B)

O

C O

OMeNO2

(C)

O

C O

OMe

NO2

(D)

O

C O

NO2

OMe

6.8 The end product of the folloowing reaction sequence is:OCH3

+

O

O

O

||Dry. AICI3 Zn Hg / HCI SOCI / Pyridine2

OH (tautomerises)H O2

Dry. AICI3


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(A)

OCH OH3

(B)

OCH3OH

(C)

CH O3 OH

(D)

CH O3

OH

6.9 The end product of following reaction is

CH COCI / AICI3 3(1)

C H COCI / AICI2 5 3(2) (3)

CIO

COO

(A) O = C

C H2 5

(C)

OOC(B) C C H2 5

O

OOC(D) COOCOO

||

OC

C H2 5

6.10 The product of the followiing reactions is

O

C CH3

|| CH C CI3

||O

AICI3

(A) C CH3

||O

OC =

CH3

(B) C CH3

||O

O

C CH3

(C) C CH3

||O

O

H C C3

(D) C CH3

||O

H C C3

O

6.11 Which of the following is best sequence of reagents for the conversion of

Br

CH3

(A)Br / Fe2 conc. H SO2 4 CH CI / AICI3 3 H O3

(B)CH CI / AICI3 3 conc. H SO2 4 Br / Fe2 H O3

(C)CH CI / AICI3 3 3CI /2 h Br / Fe2 Zn / HCI

(D)HNO + conc. H SO3 2 4 CH CI / AICI3 3 Sn / HCI NaNO / HCI2 CuBr

6.12 The intermediate product 'X' of following synthesis is identified as :

CI /FeCI2 3 conc. H SO2 4 Fuming HNO3

'X'

NH3/Cu2O/

120C 100C

dil.H So ,2 4

2, 6-Dinitroaniline


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(A)

HO S3

CI

NO2

(B)

O N2

CI

NO2

SO H3

(C)

SO H3

NO2

CI

O N2(D)

NO2

CIHO S3

SO H3

6.13 The major product of the following reaction sequence will be

OHPhCOCI / Pyridine

(1)

CH COCI/AICI3 3(2) (3)

Zn Hg / HCI /

(4)

Br /Fe2

(A) O CCH CH3 2

OBr

(C) Br O C

O

CH CH2 3

(B) H CCH3 2

Br

O C

O

(D) CH CH3 2

Br

O CH2

6.14 In the following reactions X, Y and Z are respectively :

(x) H /Ni2

NH2

OMe

Br /KOH,2 (Z)

(Y)

NaNH /NH ( )2 3 l

X Y Z

(A)

CH = NOH

OMe

CONH2

OMe

, ,

OMe

CI

(B)

OMe

NO2

,

OMe

CI

,

OMe

CONH2

(C)

MeO

CONH2,

MeO

CN,

MeO

NO2

(D)

CN

OMe

,

COO NH

4

OMe

,

OMe

CI


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6.15

NH2

CH COCI3 ABr + H O2 2 B C

H O3+

C (major product) is

(A)

NH2

Br

(B)

NH2

Br(B)

NH2

Br

(D) none of these

6.16 Which of the following is regenerated at the end of the reaction

p Nitro phenol

(X)

(C H ) SO / NaOH2 5 2 4

(1) (2)

Sn / HCI

(3)

NaNO / HCI2(Y)

C H OH6 5

(4)

(?) HI

(9) CuNO2(8)

NaNO2 NaNO2/ HCI

(7) (6)

Sn / HCI(W)

(5)(Z)

NaOH / C H Br2 5

(A) X (B) Y (C) Z (D) W

6.17 Consider the following reaction sequence

Product is:-

HNO +H SO3 2 4 Sn+HCI NaNO +HCI2

(6H)

Cu (CN) +HCN2 2 H O2 Product

(A)

CH OH2

(B)

CN

OH

(C)

COOH

(D)

NH2CN

6.18 The products R and S are respectively

NO2(X) (W)

KMnO /4 OH / Br / Fe2(R)

(Y)

Sn/HCI

KMnO /4 OH / (Z)Br / Fe2 (S)

(A)

HOOC

HOOC

Brand

HOOC

HOOC

Br

NH2HOOC

HOOC

Br

(B) : R and S are same products

(C)

HOOC

HOOC

NO2

Brand

HOOC

HOOC

Br

(D)

HOOC

HOOC Br

NO2

and

HOOC

HOOC

Br

NO2


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6.19 The end product 'Z' of the reaction sequence is

CI O

CIAICI3

XZn/Hg

Conc. HCIY

Se/Z

(A) (B)

(C) (D) Both A and B

6.20 NO2

Br

KCN/C H OH2 5A

H O3+

C. Product 'C' isNaOH+CaO

distilation

(A)

COONa

Br

(B)

Br

COONa

(C)

NO2

(D) None of these

6.21NH2

NH2HNO2 A B, Product 'B' is

(A)

N CI2+

(B)

N

N

N

H

(C)

N

N

N

H

(D) All of these


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6.22B A

NO2(1) Sn/HCI

(2) KMnO4'x'

'y'KMnO4

[O]

'x' and 'y' are respectively :

B A(A)

COOH

COOH

and

COOH

COOH

NO2

A

COOH

COOH

NH2

(B) and B

COOH

COOH

A

COOH

COOH

NH2

(C) and A

COOH

COOH

NO2

(D) B

COOH

COOH

and B

COOH

COOH

6.23 Which of the following electophilic substitution reaction represent correct product.

(A)

NO2

OCH3

Br /FeBr2 3

NO2

OCH3

Br

(B)

O O

Br /FeBr2 3

O O

Br

(C)

COOCH3

OCH3Br /FeBr2 3

Br /FeBr2 3

COOCH3

OCH3

Br

(D) CCH3

O

CCH3

O

Br6.24 Which of the followning reactions give alkylation product:

(A)

(C) + CH COCI3

+

OH

H

AICI3

(B)

(D)

+ H

+ AICI3Me C COCI3


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6.25 The following conversion reafction can be carried out by using reaction sequence/s.

O

OH

O COOH

(A)

(B)

(C)

(D)

Zn / Hg / HCI, Br2 / h KCN H3O+,

NaBH4 AI O ,2 3 O / H O (oxidative)3 2

Heat I2/NaOH, H+

KMnO / OH / heat4

6.26 Which of the following ion will be aromatic in nature?

(A)

N|H

(B)CI

HH (C)

N

(D)

NH

+

H


6.27 Statement-1 : Benzene and ethene both give reactions with electrophilic reagents.Statement-2 :Benzene and ethene both have loosely bound electrons, which can be donatedto vacant orbital of the electrophile.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


6.28 Statement-1 :

H

C

(Triphenylmethane)

is less Acidic than (Fluordane)C

H

Statement-2 : coplanar arrangement of three rings in fluordane, allows more extensivedelocalisation in conjugate anion.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.

(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation forStatement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.

6.29 Statement-1 :Polycylation in benzene does not occur during friedel Craft's acylation.Statement-2 :As the product ketone is much more reactive than starting material.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for


6.30 Statement-1 : 3AIBr3 3 2 3 22Ar C(CH ) Br ArBr CH C CH


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but 3AIBr

2 3 2 6 4 2 3ArCH CH Br o,p BrC H CH CH

Statement-2 : In the first case ipso substitution takes place in which Br displaces (CH 3)3C+, a

stable cation but removel of CH3CH2cause large amount of energy.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.

(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation forStatement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.

6.31 Statement-1 :1, 3, 5 trihydroxybenzene reacts with NH2OH togive oximino derivative where as1, 3 dihydraxy benzene do not

Statement-2: Former exist in

||

||

O

OO

which gives

NOH

NOH

NOH

where at later exists in

OH

OH

no substantial keto form is present which can give oximino derivative(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for



6.32 The product of reaction

CH OH2

of with conc. H2SO4 is

6.33 The best position for ArSE in pyridine

4

3

2

1N

is 4

SECTION - V : COMPREHENSION TYPEComprehension # 1

COOH

SOCI2 QSolid N O2 5 R

(CH ) CuLi3 2 SFe / H

T(i) NaNO2 / H

(ii) PhOH / OH(U)

6.34 The product U is

(A) C

H

CH3

N = N OH

(B) H C 3

O

C N = N||

OH

(C)

N = N OH

C

O

H C 3(D)

CH CH2 3

N = N OH


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6.35 S on reaction with CI2/ NaOH or on reaction with CI2/ NaOH followed by acidification will not givewhich of the followong

(A)

NO2

COONa(B)

CH COONa2

NO2

(C) CHCI3 (D)COOH

NO2

6.36 T on reaction with NaNO2/HCI followed by reaction with H3PO2will give.

(A)

CH COCH2 3 COCH3

(B)

CH3

(C)

COCH3

(D)

OH

COCH3

Comprehension # 2

The compound C8H9CI (A) on treatments with KCN followed ny hydrolysis gives C9H10O2 (B).Ammonium salt of B on dry distillation yields C. Which reacts with alkaline solution of bromineto gives C8H11N. (D) Another compound E (C8H10O) is obtained by the action of nitrous acid onD. or by the action of aquous potash A. E on oxidation gives F (C8H6O) Which gives the inneranhydride G on heating.

6.37 The compound A is

(A)CH CH CI2 2

(B)

CH CI2

CH3

(C)

CH CI2

CH3

(D)

CH CI2

CH3

6.38 The compound D is reacts with CHCI3+ NaOH gives a compound H. The structrure of H.

(A) (B)CH CH NC2 2

CH3

(C)

CH CN2

CH3

CH NC2

CH3

(D)

CH3

CH NH CH2 3

6.39 The compound A on reaction with AgCN gives.(A) co,pound H. (B) Compound B (C) compound G. (D) compound D

Comprehension # 3

CH CO2

CH CO2

OAICI3

(1)(X)

(C H O )10 12 2C H O10 10 3(2)

Zn(Hg) HCI/

(Y)

SOCI2

(3)

(Z) (C H OCI)10 11

(C H ) + H10 8 2(T) (S) (R)

Pt, heat(7)

(C H )10 10(6)

H SO /2 4 (C H O)10 12(5)

H / Pt2 (C H )10 10O

(W)(4)

AICI3


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6.40 What product will be obtained if 'W' is treated with C 6H5MgBr followed by D3O and then byheating?

(A)

OD

Ph Ph

(C)

(B)

(D)

OD Ph

6.41 What product is obvtained when (X) is heated with conc. H 2SO4

(A) (B) (C) (D)

O O O

O

O

O O O

6.42 What product is obtained when W is heated with KMnO4 / OH.

(A)

(C) (D)

(B)

COOHCOOH

COOHCOOH

O O

O


6.43 Match the following

Column - I Column - II

(A)

(B)

(C)

(D)

(p)

(q)

(r)

(s)

Anti aromatic

Aromatic

Non aromatic

G.F = C Hn n

e:

:e

(Non-Planar)

(Planar)

(Planar)

:e


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6.44

NO2

(1)Sn/HCI(2) (CH CO) O3 2

A B C

Br2

HNO3 Dil.

H SO2 4

H SO2 4

H SO2 4

G

(1) CuBr(2)Sn/HCI

(3) NaNO , HSO2 4F E D

H PO3 2 NaNO2

HBF ,4

H

Write the correct combinations

Column-I Column-II

(A) A(p)

Br

Br Br

(B) B(q)

Br

F

Br Br

(C) G

(r)

NHCOCH3

NO2

(D) H

(s)NHCOCH3


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6.45 Match the correct properties of compounds of column I with column II.

(I) (II)

(A)

OCH=CH2

(p) Gives Benzoic acid with hot alkaline KMnO4

(B)

CH=CH2

(q) o/p directing and activating for E

(C)

CHCH3

OH (r) Gives fastest reaction with an electrophile

(D) CH3

O

C(s) Gives an ester on reductive ozonolysis


SHORT SUBJECTIVE:

6.46

NO2

(I) (II) (III) (IV) (V)

OH

(C H ) SO2 5 2 4 Zn/HCI/ NaNO , HCI2 Phenol Br /H O2 2NaOH (4) (5)OH (1)

(2) 5C (3)

The steps involved in the above reaction can be arranged as.Electrophilic substitution = step (w)Nucleophilic substitution=step (x)Reduction reaction = step (y)Diazocoupling reaction = step (z)

Assign the correct numbers to the type of reactions as follows w x y z

6.47 Observe the following reaction sequence

Phenol(1)

(X) (Y) (Z)NaOH (1 eq) HCN, HCI/AICI3 NH NHPh2

Me

D I

H

(3) (4)

(2)

Answer the following questions in the given format :

P Q R S

P = Number of organic products formed in step-1Q = Number of organic products formed in step-2 (singnificant products)

R = Number of organic products formed in step-3 (singnificant products)S = In which step aromatic electrophilic substitutiion has taken place


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6.48 CH CI/AICI3 3

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Questions Chapter 1-10