1 ISOMERISM

CHAMPIONS LECTURE SERIES

C–130
Time: 2 Hrs

Lecture Planning & Flow

No. Lecture Contents Homework of this lecture

Structural Isomerism, Types of Isomerism; Position; For CET Aspirants

Functional; Metamerism, Ring Chain.
II
III Isomerism, Stereo : Geometrical, Types of
Stereoisomerism;Geometrical/Configurational
Isomers, Configurational Nomenclature; Sequence
Rules,
IV Stereo : Optical, Introduction to Optical Activity,
Element of Symmetry, Projection Formula,
Configurat ion Nomenclat ure,E nantiomers ,
Diastereomers, Meso Compound, Optical Activity
without Asymmetric Carbon.
V Conformational Isomerism, Newman Projection,
Analysis Conformers of Ethane and Butane,
Stability of Conformers
Solve Abhyaas (Level-I) and state
board questions with detailed analysis
and solution (Don't Just write the
answer) that can be written in the
space provided in the Abhyaas.
For JEE Main/NEET Aspirants
Solve Abhyaas (Level-I) and NCERT
questions with Detailed analysis and
solutions (Don't just write the answer)
that can be written in the space
provided in the Abhyaas.
For JEE Advanced Aspirants
Solve Abhyaas Level-I and Level-II
Questions with detailed analysis and
solution (DonÊt just write the answer)
that can be written the space provided
in the Abhyaas.
In addition to abhyaas you can do
problems from following reference
books

(1) MS Chauhan (Elementary)

Page : 17 (Q.1-39)
Has the student completed the homework of the previous lecture ?
(2) MS Chauhan (Advanced)
Page : 71 (Q.1-37)
Roll No. STAMP
(3) Himanshu Pandey
Page : 78 (Q.1-17)

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CHEMISTRY 2

ISOMERISM

DEFINITION OF ISOMERISM..
When two or more compounds have same molecular formula but they differ in their physical properties or
chemical properties or both then they are called isomers & the phenomena is called isomerism.
Classification of Isomerism
Isomerism

Structural (constitutional) Stereo (configurational & conformational)

isomerism isomerism

Chain Position Functional Metamerism Tautomerism

isomerism isomerism group isomerism

STRUCTURAL ISOMERISM..
When two or more organic compounds have same molecular formula but different structural formula,
(i.e., they differ in connectivity of atoms) then they are called structural isomers and the phenomena is called
structural isomerism
Structural isomers have always different IUPAC name
CH 3  CH  CH  CH 3 CH3 CH2 CH  CH2 
Illustration-1 , structural Isomers
But  2  ene But  1  ene 

CH3
| CH 3  CH  CH 2 CH 3  Identical compounds
CH  CH2  CH3 |  (not isomers)
Illustration-2 | , CH 3 
CH3 2  Methylbutane 
2  Methyl butane

ISOMERS CHARACTERISTICS CONDITIONS

They have different size of main chain or
(1) Chain isomers They have same nature of locants
side chain

Molecules with saturated cyclic structures

(2) Ring chain Cyclic - saturated open chain - unsaturated.
& unsaturated open chain

They should have same size of main chain and

(3) Positional isomers They have different position of locants
side chain and same nature of locant
Chain and positional isomerism is not
(4) Functional isomers Different nature of locant
considered

Different nature of alkyl group along a They should have same nature of functional
(5) Metamerism
polyvalent functional group groups chain & positional isomer is ignored

Different position of hydrogen atoms

(6) Tautomerism The two functional isomers remains in
dynamic equilibrium to each other

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 3 ISOMERISM

CHAIN ISOMERISM OR NUCLEAR ISOMERISM OR SKELETAL ISOMERISM

Chain isomers have the same molecular formula but differ in the order in which carbon atoms are bonded to
each other.This type of isomerism is due to difference in the arrangement of carbon atoms i.e. straight or
branched chain of carbon atoms. It is also known as nuclear or skeletal isomerism
Condition : – 1. Size of main chain or side chain or both should be different.
2. Nature of functional group, multiple bond or substituent should not change.
CH3
Illustration-3 (A) CH3 – CH2CH2 – CH3
CH3 – CH – CH3
Butane 2–Methylpropane
Size of main chain = 4 Size of main chain = 3
Size of side chain = 0 Size of side chain = 1
Isomeric pair :
When more than one structure can be written with a given molecular formula, each of the structure
with respect to any other structure is called an isomeric pair.
C5H12
CH3
|
CH3·CH2·CH2·CH2·CH3 , CH3·CH2·CH·CH3 , CH3·C·CH3
3
| 2
| 3
CH3 CH3
Illustration-4

1 & 2 , 2 & 3 , 1 & 3 are chain isomer pairs.

N o. of
M olecula r Form ula N o. of Isom ers
C a rbon Atom s
1 CH 4 1
2 C 2H 6 1
3 C 3H 8 1
4 C 4H 10 2
5 C 5H 12 3
6 C 6H 14 5
7 C 7H 16 9
8 C 8H 18 15
9 C 9H 20 35
10 C 10H 22 75
15 C 15H 32 4347
20 C 20H 42 36,719

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CHEMISTRY 4
Chain isomerism in alicyclic compounds :
Illustration-5 C8H16

1–Ethylcyclohexane
1,4–Dimethylcyclohexane
Size of main chain = 6 Size of main chain = 6
Size of side chain = 2 Size of side chain 1 = 1
Size of side chain 2 = 1

Illustration-6
Cyclohexane 1,2,3–Trimethylcyclopropane
Size of main chain = 6 Size of main chain = 3
Size of side chain = 0 Size of side chain 1 = 1
Size of side chain 2 = 1
Size of side chain 3 = 1

Illustration-7
1 2 3 4 5
2, 3, 4, 5 are chain isomers of 1.
(2, 3) (2, 4) (4, 5) (3, 4) (3, 5) (4, 5) pairs are not chain isomers.

Chain isomerism in aromatic compounds

(1) (2) (3) (4)

POSITION ISOMERISM..

When two or more organic compounds have same molecular formula but they differ in the position of the
functional group or the substituent, then they are called position isomers & the phenomena is called position
isomerism.
Condition : Same size of main chain or side chain but different position of group or substituents or functional
group.

H 3 C  CH 2  CH  CH 2 (but  1  ene) 
Illustration-8 (a) position isomers
H 3 C  CH  CH  CH 2 (but  2  ene) 

HC  C  CH 2  CH 2  CH 3 (pent  1  yne) 
(b) H C  C  C  CH  CH  position isomers
(pent  2  yne) 
3 2 3

H 3 C  H 2 C  H 2 C  Cl (1  chloropropane) 
(c) 
(2  chloropropane) position isomers
H 3 C  CH  CH 3 Isopropyl chloride 
| 
Cl

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 5 ISOMERISM

Cl
(d) H2C = C Cl – CH = CH – Cl] position isomers
Cl
(dichloro ethene) (dichloroethene)
or (ethylidene chloride) or (ethylene chloride)

(e) C8H10 (3-aromatic position isomers)

(I) (II) (III) position isomers

o-xylene m-xylene
p-xylene
(f) C7H7NO2 (3-aromatic position isomers)
NO2 NO2
NO2
CH3
(I) (II) (III)
CH3
CH3

(g) C6H3 (OH)3  (3 aromatic position isomers)

OH OH OH
OH OH
(I) (II) (III)
OH OH OH
OH

Illustration-9 CH3 – CH2OH CH3 – O – CH3

Ethanol Methoxymethane
O O
CH3 – C – OH H – C – OCH3
Ethanoic acid Methyl methanoate
(I) and (II) are chain isomers (I) and (III) are chain isomers
(I) and (IV) are position isomers (II) and (III) are position isomers
(II) and (IV) are chain isomers (III) and (IV) are chain isomers

FUNCTIONAL ISOMERISM

Compound having same molecular formula but different functional groups in their molecules show functional
isomerism and are called functional isomers.

Formula Functional Isomers

(i) CnH2n Alkene, Cycloalkane
(ii) CnH2n-2 Alkadiene, Alkyne, Cycloalkene
(iii) CnH2n+2O Alcohol, Ether
(iv) CnH2nO Aldehyde, Ketone, Oxirane (epoxy)
Acid, ester, hydroxy, carbonyl
(v) CnH2nO2
(aldehyde, ketone compounds)

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CHEMISTRY 6

Illustration-10 C4H8O2
H 3 C  CH  C  CH 3 & CH 3  CH 2 CH 2 COOH
| ||
OH O

Illustration-11 Functional isomers of CH3 – C  CH is

(A) CH2 = C = CH2 (B)

(C) (D) Both A and B

Ans. (D) (Hint : sp carbon not possible in C3–C7 rings.)

RING CHAIN ISOMERS

When two or more organic compounds have same molecular formula but they differ in their structures due to
one being a cyclic compound & the other one an open chain compound, then they are called ring chain isomers
& the phenomena is called ring-chain isomerism or functional isomerisum.

Illustration-12 Write all isomers of C4H8 and indicate relationship between them : C4H8

but-1-ene cyclobutane but-2-ene 2-methylcyclopropane 2-methylprop-1-ene

(1) (2) (3) (4) (5)

Illustration-13 Compound CH3 – CH2 – CH2 – C  CH and show..

(A) Position isomers (B) Chain isomers
(C) Ring chain isomers (D) All of these
Ans. (C)

Illustration-14 1, 2–Epoxy propane and prop–2–en–1–ol (Allyl alcohol) are

(A) Position isomers (B) Functional isomers
(C) Ring chain isomers (D) Both B and C
Ans. (D)

METAMERISM

This type of isomerism is due to the difference in the nature of alkyl groups attached to the polyvalent atom or
functional group. Metamers belong to the same homologous series. Compounds like ethers, thioethers, secondary
amines etc. show metamerism.
Condition :
1. Functional group should be polyvalent, heteroatomic.
2. Nature of functional group should not change
3. Chain and position isomerism is not considered.

Illustration-15 C2H5 – O – C2H5 C3H7 – O – CH3

Diethyl ether Methyl propyl ether
Hydrocarbon groups – C2H5 , – C2H5 Hydrocarbon groups – C3H7, – CH3

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 7 ISOMERISM

CH3 C2H5
C3H7 – N C2H–N
Illustration-16 CH3 CH3
Dimethyl propylamine Diethyl methylamine
Hydrocarbon groups –CH3 , –C3H7 Hydrocarbon groups
– CH3, – C2H5 , – C2H5

O O
Illustration-17 CH3CH2 – C – O – CH3 CH3 – C – O – CH2CH3
Methyl propanoate Ethyl ethanoate

O O
|| ||
Illustration-18 Compound CH 3  CH 2  C  NH  CH 3 and CH 3  C  NH  CH 2  CH 3 are
( I) ( II)

(A) Functional isomers (B) Position isomers

(C) Metamers (D) All of these
Ans. (C)

Illustration-19 Metamer of the compound P is

O
P= C O

O O
(A) C O (B) O C

O
(C) O C (D) All of these

Ans. (C)

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CHEMISTRY 8

ABHYAAS - I
LEVEL - I
Q-1 Fill in the blanks:
(a) The number of possible isomers of C5H12 is ___________.
(b) Hexane has ___________ chain isomers.

(c) n-Butane and isobutane are ___________ isomers.

(d) The chain isomers of n-pentane are isopentane and ___________.

(e) There must be minimum ___________ carbon atoms to exhibit chain isomerism.

(f) The possible number of dichloro derivatives of propane are ___________ .

(g) Ethyl benzene is ___________ isomer to xylenes.

Soln:

Q-2 The name of which carbon chain starts from 'iso' in the following chains –
CC CC
| | |
(A) C  C  C (B) C  C  C  C (C) C  C  C  C (D) C  C  C
| | |
CCC CCC
Soln:

Q-3 The total possible number of chain isomers for the molecular formula C 5H12 would be –
(A) 3 (B) 2 (C) 4 (D) 5

Soln:

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 9 ISOMERISM

Q-4 Out of following carbon chains which one is different from other three chains –
(A) C C C C (B) C C C C (C) C C C C (D) C C C
C C C C C C C C C C C C C C

Soln:

Q-5 2-chlorobutane & 3-chlorobutane are-

(A) Positional isomers (B) Chain isomers (C) Geometrical (D) identical structures

Soln:

Q-6 Which one of the following pairs are called position isomers –
(A) CH2 (OH) CH2COOH & CH3 - CH (OH) COOH
(B) C2H5OH & CH3OH

(C) (C2H5)2CO & CH3COCH2CH2CH3

(D) All the above

Soln:

Q-7 and are called as –

(A) Position isomers (B) Chain isomers (C) Function isomers (D) Ring chain isomers

Soln:

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CHEMISTRY 10
Q-8 Methyl propyl thioether and isopropyl methyl thioether are –
(A) Metamers (B) Position isomers
(C) Chain isomers (D) Chain and position both

Soln:

Q-9 Possible number of disubstituted benzene isomers is –

(A) 1 (B) 2 (C) 3 (D) 4

Soln:

Q-10 Which of the following are isomers -

(A) Ethanol and ethoxy ethane (B) Methanol and methoxy methane
(C) Propanoic acid and ethyl acetate (D) Propionaldehyde and acetone

Soln:

Q-11 Functional isomer of CH3COOCH3 is –

(A) CH3CH2COOH (B) HOCH2—CH2CHO
(C) Both of the above (D) None of the above

Soln:

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 11 ISOMERISM

Q-12 How many aliphatic carbonyl compounds are possible having the molecular formula
C5H10O –
(A) 4 (B) 5 (C) 6 (D) 7

Soln:

Q-13 and are –

(A) Tautomers (B) Functional (C) Position (D) All the above

Soln:

Q-14 O - Cresol & benzyl alcohol are –

(A) Functional (B) Position (C) Chain (D) All the above

Soln:

Q-15 CH3CONH2 & HCONHCH3 are called –

(A) Position (B) Chain (C) Tautomers (D) Functional

Soln:

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CHEMISTRY 12
Q-16 The formula C4H8O2 represents –
(A) Only an acid (B) Only an ether (C) Only an alcohol (D) Both ether and alcohol

Soln:

Q-17 Propene and cyclopropane are – `

(A) Chain isomers (B) Position isomers
(C) Geometrical isomers (D) Ring chain isomer

Soln:

Q-18 The number of ether metamers represented by the formula C 4H10O is -

(A) 4 (B) 3 (C) 2 (D) 1

Soln:

Q-19 Metamerism is shown by -

(A) Diethyl ether and n-propyl methyl ether (B) Ethyl alcohol and diethyl ether
(C) Acetone and propionaldehyde (D) Propionic acid and acetic acid

Soln:

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 13 ISOMERISM

Q-20 Which of the following pairs of compounds are not metamers ?

(A) CH3OCH2CH2CH3 and CH3CH2OCH2CH3

(B) CH3CH2OCH2CH3 and CH3OCH(CH3)2

(C) CH3NHCH2CH2CH3 and CH3CH2NHCH2CH3

(D) CH3NHCH2CH2CH3 and CH3NHCH(CH3)2

Soln:

Q-21 Type of isomerism exists between :-

CH3—CH2—CH2—CN and CH3  CH  CH3

|
CN

(A) Position (B) Chain (C) Both the above (D) None of these

Soln:

Q-22 The number of primary alcohols possible with the formula C4H10O is -
(A) 2 (B) 3 (C) 4 (D) 5

Soln:

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CHEMISTRY 14

Q-23 The total number of benzene derivatives having the molecular formula C7H7Cl is -
(A) 2 (B) 3 (C) 4 (D) 5

Soln:

Q-24 The total number of cyclic compounds (neglecting stereoisomers) with the molecular formula C5H10 is -
(A) 4 (B) 5 (C) 6 (D) 7

Soln:

Q-25 The total number of benzene derivatives having the molecular formula C7H8O is -
(A) 3 (B) 4 (C) 5 (D) 6

Soln:

Q-26 The total number of benzene derivatives with the molecular formula C6H3Cl3 is -
(A) 2 (B) 3 (C) 4 (D) 5

Soln:

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 15 ISOMERISM

Q-27 The total number of aldehydes and ketones with the molecular formula C4H8O is -
(A) 2 (B) 3 (C) 4 (D) 5

Soln:

Q-28 When C 6H 4Cl 2 is converted into C 6H 3Cl 3, m-isomer will give n types of C 6H 3Cl 3, and p-isomer
will give q types of C6H3Cl3. m, n, q are respectively :
(A) 1, 2, 3 (B) 2, 1, 3 (C) 1, 3, 2 (D) 2, 3, 1

Soln:

Q-29 Which of the following statements are correct :-

CH 3
|
(A) CH3CH2CH2CH2OH and CH 3 CHCH 2OH represent chain isomerism

(B) CH3CH2CH2CH=CH2 and CH3CH2CH = CHCH3 are examples of position isomerism

(C) C2H5OCH3 and CH3CH2CH2OH represent functional-group isomerism

(D) CH3CH2NH2 and CH3NHCH3 are examples of metamerism

Soln:

Q-30 How many cyclic structures are possible for C4H6 :-

(A) 3 (B) 5 (C) 4 (D) 6
Soln:

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CHEMISTRY 16

Q-31 Observe the following structures and answer the questions given below.
(i) CH3 – CH2 – CH2 – CHO [HSC]
(ii) CH 3  CH  CHO
|
CH 3

(a) What is the relation between (i) and (ii) ?

(b) Write IUPAC name of (ii).
(c) Draw the functional group isomer of (i).
Soln:

Q-32 Observe ther following and answer the question given below:
 
U.V.light
CH 3  CH 3   C H3  C H3
(a) Name the reactive intermediae produced
(b) Indicate the movement of electrons by suitable arrow to produce this intermediate
(c) Comment on stability of this intermediate [HSC]
Soln:

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 17 ISOMERISM

ANSWERS
LEVEL - I
Q-1 Fill in the blanks
(a) Three (b) Five (c) Chain (d) Neopentane
(e) Four (f) four (g) chain

Q-2 (A) Q-3 (A) Q-4 (B) Q-5 (D) Q-6 (A) Q-7 (A) Q-8 (B)

Q-9 (C) Q-10 (D) Q-11 (C) Q-12 (D) Q-13 (B) Q-14 (A) Q-15 (D)

Q-16 (A) Q-17 (D) Q-18 (C) Q-19 (A) Q-20 (D) Q-21 (A) Q-22 (A)

Q-23 (C) Q-24 (A) Q-25 (C) Q-26 (B) Q-27 (B) Q-28 (D) Q-29 (ABCD)

O
||
Q-30 (C) Q-31 (a) Chain isomers (b) 2 – methylopropanal (c) CH 3  CH 2  C  CH 3

Q-32 (a) Intermediate - Free readical (e – deficient)

 
(b) CH 3  CH 3 
UV light
Homolysis
 C H3  C H3


(c) C H Highly unstable, e – deficient
3

intermediate  very reactive

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 1 ISOMERISM

CHAMPIONS LECTURE SERIES

Level-II
C-130 To C-134

Lecture Planning & Flow

Abhyaas Homework of lectures Remark
Abhyaas-I (1) MS Chauhan (Elementary) Page : 17 (Q.1-39) Yes   No  
(2) MS Chauhan (Advanced) Page : 71 (Q.1-37) Yes   No  
(3) Himanshu Pandey Page : 78 (Q.1-17) Yes   No  

Abhyaas-II (1) MS Chauhan (Elementary) Page : 20 (Q.1-22) Yes   No  

(2) MS Chauhan (Advanced) Page : 79 (Q.38-74) Yes   No  
(3) Himanshu Pandey Page : 79 (Q.18-55) Yes   No  

Abhyaas-III (1) MS Chauhan (Elementary) Page : 28 (Q.1 - 25) Yes   No  

(2) MS Chauhan (Advanced) Page : 87 (Q.75 -108) Yes   No  
(3) Himanshu Pandey Page : 69 (Q.1 - 50) Yes   No  

Abhyaas-IV (1) MS Chauhan (Elementary)

Page : 31 (Q.1-64), Page : 43 (Q1-12) Yes   No  
(2) MS Chauhan (Advanced) Page : 94 (Q.120 - 144) Yes   No  
(3) Himanshu Pandey Page : 86 (Q.1-125) Yes   No  

Abhyaas-V (1) MS Chauhan (Elementary) Page : 25 (Q.1 - 14) Yes   No  

(2) MS Chauhan (Advanced) Page : 99 (Q.145 - 185) Yes   No  
(3) Himanshu Pandey Page : 110 (Q.1 - 45) Yes   No  

Has the student completed the homework of the previous lecture ?

Roll No. STAMP

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CHEMISTRY 2

ABHYAAS - I

LEVEL - II

Q-1 Write all acyclic structural isomers of C5H10.

Soln:

Q-2 Find the hybridization state of each carbon atoms in following compound.
CH2 = C = CH – CH2 – C  C – CH2 – NH2

Soln:

Q-3 Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon
atoms only.

Soln:

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 3 ISOMERISM

Q-4 Which isomerism is shown by C–O and H–C–O

O O
Soln:

Q-5 The ring chain functional isomer of compound But-2-ene are.

Soln:

Q-6 Write all cyclic isomers of C3H6O.

Soln:

Q-7 Identify the molecular weight of the compound ‘X’ containing carbon and hydrogen atoms only with 3
and 2 bonds in one molecule.

Soln:

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CHEMISTRY 4
Q-8 Identify the relationship between the given compounds.

(i) and (ii) OH and

OH

(iii) CN and (iv) O and

CN O
O O O O
(v) H and (vi) and
O O H O O
Soln:

Q-9 Mention the correct relationship between (I) and (II)

SO3H Br
Br

HO3S SO3H
|

Br SO3H
(I) Br (II)
Soln:

Q-10 Which of the following shows functional isomerism ?

(A) CH3CH2Cl and CH3CH2Br (B) CH3CH2Br and CH2 BrCH2Br
(C) C2H5OC2H5 and CH3OC3H7 (D) CH3CH2CHO and CH3COCH3

Soln:

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 5 ISOMERISM
Q-11 An organic compound has molecular formula C9H18. Its all carbon atoms are sp3 hybridised and its
all hydrogen atoms are identical. Its structural formula can be :
Soln:

Q-12 Which compound is not the isomer of 3-Ethyl-2-methylpentane ?

(A) (B)

(C) (D)

Soln:

Q-13 Cl
Cl Cl

Cl

Relation between above compounds is :

Soln:

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CHEMISTRY 6

Q-14 Total number of position isomers of dimethyl cyclohexane.

Soln:

Q-15 Which type of isomerism is observed between I and II ?

CH 3 – CH 2 – C– OCH 3 CH 3 – C– OC 2 H 5
|| ||
O , O
(I) (II)

Soln:

Q-16 Which of the following is a pair of metamers ?

O
O O
(A) (B) O
O O

Br
Cl
I
(C) H2N
(D)
NH2 Cl
Br
I

Soln:

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 7 ISOMERISM

Q-17 Which of the following is not an isomer of compound CH3 – CH2CHO

(A) (B) (C) (D) CH2=CH–CH2–OH

O
Soln:

Q-18 The isomer of diethyl ether is

(A) (CH3)2CHOH (B) (CH3)3COH (C) C3H7OH (D) (C2H5)2CHOH

Soln:

Q-19 How many total structural isomers are obtained when three hydrogen atoms are replaced by chlorine

atom from molecular formula C3H8 ?

Soln:

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CHEMISTRY 8

Q-20 Consider the following structures.

CH3
Cl
CH 3 – CH 2 – CH 2 – CH 2 – Cl CH3 – C – CH3
Cl – CH2 – Cl
I II III IV

(A) I & II are chain isomers (B) I & III are functional isomers
(C) II & IV are functional isomers (D) III & IV are chain isomers
Soln:

Q-21 How many isomers are there corresponding to the formula C4H10O ?
Soln:

Q-22 Write structural isomer of C6H14. What is relation between them ?

Soln:

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 9 ISOMERISM
Q-23 The enolic form of acetone contains :
(A) 9 bonds, 1 bond and 2 lone pairs
(B) 8 bonds, 2 bonds and 2 lone pairs
(C) 10 bonds, 1 bonds and 1 lone pair
(D) 9 bonds, 2 bond and 1 lone pair

Soln:

Q-24 The compound which is not isomeric with diethyl ether is :

(A) butan–1–ol (B) butanone
(C) 2–methyl propan–2–ol (D) n–propyl methyl ether

Soln:

Q-25 The number of structural isomers of C6H14 is :

(A) 3 (B) 4 (C) 5 (D) 6
Soln:

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CHEMISTRY 10
Q-26 Match the Column-I with Column-II
Column-I (Reaction) Column-II (Stereoisomers)

(A) & Cl (p) Homologs

Cl

OCH2–CH3 OCH3
CH3
(B) & (q) Functional isomers

OCH3 OH
CH3
(C) & (r) Metamer

(D) CH3–CH2– –CH2–CH3 & (s) Chain isomers

CH3– –CH2–CH2–CH3

Soln:

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 11 ISOMERISM

ABHYAAS - II
LEVEL - II

Q-1 Which of the following will show tautomerism.

(A) Butanal (B) Butanone (C) Cyclohexanone (D) Ph · C · Ph
||
O

Soln:

Q-2 Write tautomer of the following compounds

O
(i) CH3 – CH = NH (ii) CH3 – C – CH3 (iii) CH3 – CH – NO2 (iv) CH3  C  CH2  C  CH3
|| ||
CH3 O O

Soln:

Q-3 Monocarbonyl compounds have very small percentage enol form at equilibrium. Explain.

Soln:

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CHEMISTRY 12
Q-4 Tautomerism is exhibited by :

(A) CH = CH – OH (B) O O

(C) O (D) O

O O

Soln:

Q-5 Tautomerism will be exhibited by :

(A) (CH3)2NH (B) (CH3)3CNO (C) R3CNO2 (D) RCH2NO2

Soln:

Q-6 Which of the following will not show tautomerism ?

H 3C (H3C)3C N=O
(A) C=N (B) C=C
H OH H3C CH3

N=O H3C
(H3C)3C C=N
C=C H3C
(C) (D) C=C OH
(H3C)3C C(CH3)3 H H

Soln:

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 13 ISOMERISM
Q-7 How will you distinguish between Maleic acid and Fumaric acid ?
Sol :
n

Q-8 Which of the following pairs show tautomerism.

O HO
+
(a) OCH3 and OMe (b) and
H3C·C·NMe2 H3C·C·NMe2 N N
H

Soln:

Q-9 What is relation between (a), (b), (c) ?

–
O O
OH
+ +
HN NH HN NH
N N
(a) (b) (c) +
N – N –
O O O O
HO N OH
H H
Soln:

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CHEMISTRY 14
Q-10 Identify the compound that exhibits tautomerism :-
(A) 2-Pentanone (B) Phenol (C) 2-Butene (D) Lactic acid
Sol :
n

Q-11 Tautomerism is not exhibited by :

(A) CH=CH–OH (B) O O

O
(C) (D) O
O
O
Sol :
n

Q-12 Which of the following will show tautomerism.

(A) D 3 C · C · CD 3 (B) CH3

||
O CH3
O

(C) CH2=CH·OH (D) HO·CH=CH·OH

Soln:

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 15 ISOMERISM

ABHYAAS - III
LEVEL - II

Q-1 The correct relationship among the following pairs of given compounds is
O O O
|| || O
|| O ||
O O
O ||
O O ||
O
(I) (II) (III) O

(I, II) (II, III)

(A) Functional Isomers Metamers
(B) Metamers Functional isomers
(C) Metamers Metamers
(D) Functional Isomers Functional isomers
Soln:

Q-2 How many acyclic structural isomers of C5H10 can show geometrical isomerism ?
Soln:

Q-3 Find the total number of geometrical isomers of following compounds.

(I) (II)
Soln:

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CHEMISTRY 16

Q-4 How many cyclic structural isomers of C5H10 can show geometrical isomerism.
Soln:

Q.5 Calculate total number of possible geometrical isomers of Ph – CH = CH – CH = CH – COOH.

Soln:

Q.6 Write all carbonyl compounds with molecular formula C3H6O and then react with excess of NH2OH and

find out how many total isomeric oximes are formed.

Soln:

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 17 ISOMERISM

Q-7 Indicate whether each of the following compound is 'E' or 'Z'.

CH3 Cl I CH3 D H H CH2Cl
(i) C=C (ii) C=C (iii) C=C (iv) C=C
Cl
H Br H C3H7 H D CH3

Soln:

Q-8 Geometrical isomers differ in :

(i) position of functional group (ii) spatial arrangement of atoms
(iii) position of atoms (iv) length of carbon chain

Soln:

Q-9 Which of the following compound does not have restricted rotation ?
CH3
CH3 CH3
| |
Br CH3
(A) CH3 (B) (C) C=C (D) H · C · C · H
Cl H | |
Br Br
Soln:

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CHEMISTRY 18

Q-10 Which compound can show geometrical isomerism ?

(A) CH3CH = C(CH3)2 (B) CH3CH = CH2
(C) CH3CH = CHCH3 (D) (CH3)2C = C(CH3)2
Soln:

Q-11 Which of the following will not show cis-trans isomerism ?

(A) CH3 – C = CH – CH2 – CH3 (B) CH3 – CH – CH = CH – CH 2 – CH3

| |
CH3 CH3
(C) CH3 – CH = CH – CH3 (D) CH3 – CH2 – CH = CH – CH2 – CH3

Soln:

Q.12 Which is a pair of geometrical isomers ?

Cl Br Cl Br Cl CH3 H Br
(I) C C (II) C C (III) (IV) C C
||

C C
||
||

||

H Br H CH3 Br H Cl CH3

Soln:

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 19 ISOMERISM

Q-13 The 'E'-isomer is :

F H H 3C CH3
(A) C C (B) C C

||

||
Cl Br H H
H 3C C2H5
(C) C C (D) none of the above

||
H CH(CH3)2

Soln:

Q-14 The correct stereochemical formula of Trans-3-chloro-1-phenylbut-1-ene is

Soln:

Q-15 Which of the following compound can not show geometrical isomerism ?

Br CH3 H3C CH3 CH3

| CH3
Br
(A) (B) (C) (D)
Cl H3C CH3 H3C CH3
Cl
Soln:

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CHEMISTRY 20

Q-16 The total number of geometrical isomers possible in following compound is :

Ph – HC = HC CH = CH – CH3

Soln:

Q-17 The total number of geometrical isomers possible in following compound is :

CH = CH – CH = CH

Soln:

Q-18 The number of geometrical isomers in the following compound is :

CH3–CH = CH – CH = CH – C2H5

Soln:

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 21 ISOMERISM

Q-19 The 'Z'-isomer is :

Cl H Cl CH3
(A) C C (B) C C

||
||
F Br F C2H5
CH3 Cl HOOC COOH
(C) C C (D) C C

||

||
C2H5 COOH H H

Soln:

Q-20 Cis-trans isomerism is shown by :

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

Soln:

Q-21 Match the column:

Column-I (reaction) Column-II (stereoisomers)

(A) CH3—CH CH—CH N—OH (p) 2

(B) (q) 4

(C) CH3—CH CH—CH CH—CH CH—CH3 (r) 6

(D) CH3—CH CH—CH CH—CH CH—Ph (s) 8
Soln:

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CHEMISTRY 22
Q-22 If the bonds in dichloro benzene, C 6 H 4 Cl 2 , were localized between specific carbon atoms,
how may isomers of this compound would exist ? How many isomers actually exists.

Soln:

Q-23 Which of the following compounds can exist as geometric isomers ?

CH2Cl2, CH2Cl—CH2Cl, CHBr = CHCl, CH2Cl—CH2Br.

Soln:

Q-24 Why does cyclopentene not exhibit geometric isomerism though it has a double bond.

Soln:

Q-25 Why does 2-butene exhibit cis-trans isomerism but 2-yne does not ?

Soln:

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 23 ISOMERISM
Q-26 N-methylethenamine as such does not show any stereoisomerism but one of its resonance form
exhibit stereoisomerism. Explain.

Soln:

Q-27 2,4-Hexadiene has three geometrical isomers. Draw their structures.

Soln:

Q-28 Geometrical isomerism is not shown by-

(A) 1,1–dichloro–1–pentene (B) 1,2–dichloro–1–pentene

(C) 1,3–dichloro–2–pentene (D) 1,4–dichloro–2–pentene

Soln:

Q-29 The alkene that exhibits geometrical isomerism is :-

(A) 2–butene (B) 2–methyl–2–butene
(C) Propene (D) 2–methyl propene

Soln:

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CHEMISTRY 24
Q-30 Maleic acid and fumaric acids are :-
(A) Tautomers (B) Chain isomers
(C) Geometrical isomers (D) Functional isomers

Soln:

Q-31 Which of the following compound will exhibits geometrical isomerism :

(A) 1–phenyl–2–butene (B) 3–phenyl–1–butene
(C) 2–phenyl–1–butene (D) 1, 1–diphenyl–1–propene

Soln:

Q-32 Which of the following exhibits stereoisomerism–

(A) 2–Methylbutene–1 (B) 3–Methylbutyne–1
(C) 3–Methylbutanoic acid (D) 2–Methylbutanoic acid

Soln:

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 25 ISOMERISM

Q-33 Which of the following has the lowest dipole moment :

CH3 CH3
(A) 7 C=C (B) CH3–CC–CH3
H H
(C) CH3CH2CCH (D) CH2=CH–CCH
Soln:

Q-34 The number of stereoisomers obtained by bromination of trans–2–butene is :

(A) 1 (B) 2 (C) 3 (D) 4
Soln:

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CHEMISTRY 26

ABHYAAS - IV
LEVEL - II
Q-1 Find plane of symmetry and centre of symmetry (if possible) in the following compounds.

H Cl Cl Cl
(I) C C (II) C C
Cl H H H

Cl

F Br
(III) C C (IV)
Cl I
Cl Cl
H
COOH H

(V) H C 3
CH3
(VI) Ph H
H Ph
H
H COOH
Soln:

Q-2 Find total number of chiral carbon atoms in the following compounds :

COOH
(I) (II)
COOH
COOH
COOH CH3

(III) (IV)
Soln:

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 27 ISOMERISM

Q-3 Find relationship between the given pairs.

F Br F I
H Cl D F
(I) Br Cl
and I F
(II) and
D I Br H
I Cl
Br Cl

COOH COOEt COOH COOH

H OH H OH H OH HO H
(III) and (IV) and
HO H HO H HO H H COOH
COOEt COOH COOH OH

Soln:

H
OH
C2H5 C
Q-4
H C
OH
CH3

Fischer projection formula of this compound can be represented as :

Soln:

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CHEMISTRY 28
Q-5 Which type of isomerism is observed between I and II ?
O Br O

CH3 – CH – S – O CH3 – CH – O – S
|
Br O
, O
H 3C C H3 (II) C H3
(I) H 3C

Soln:

Q-6 Which of the following compound has plane of symmetry (POS) but not centre of symmetry (COS) ?

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

F
Soln:

Q-7 The smallest alcohol which exhibit optical activity ?

(A) n-Butyl alcohol (B) Butan-1-ol (C) Pentan-2-ol (D) Butan-2-ol
Soln:

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 29 ISOMERISM

Q-8 Which of the following compound is optically inactive ?

CH3
OH
|
(A) CH 3 – CH 2 – CH – CH 3 (B)

H 3C CH3 CH3

(C) (D)

H Cl

Soln:

Q-9 Observe the following structures I to III - Which one has chiral centre & Dssymmetry?
C2 H 5 – CH – C2 H 5 (CH 3 )2 CH – CH – CH – CH 3 CH3 – CH – CH – CH3
| | | | |
CH3 OH CH 3 OH CH3
( ) (  ) ( )

Soln:

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CHEMISTRY 30
Q-10 Number of chiral carbon atoms in the compound x, y and z respectively would be :
Me Me
Me Me

X Y
Z
Sol :
n

Q-11 The instrument which can be used to measure optical activity, i.e., specific rotation:
Sol :
n

Q-12 Number of chiral carbon persent in the following compound :

CH3 – CH – CH2 – CH – CH – CH3
| | |
OH Br C2H5

Soln:

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 31 ISOMERISM

Q-13 Which of the following compound has ‘S’ configuration ?

CH3 OH CH3 CH3

(A) H OH (B) Br CH3 (C) Br OH (D) HO Br
Br H H H
Soln:

Q-14 Which of the following compound has 'D' configuration ?

CH3 CH3 CH3 CH3

(A) H OH (B) H NH2 (C) NH2 H (D) H OH
CHO CH2OH CH2OH CH2OH

Soln:

Q-15 The correct configuration assigned for given compound :

CH3
H OH
H NH2
Soln: CH3

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CHEMISTRY 32
Q-16 The IUPAC name of the compound is :

CH3
HO H
H Cl
C2H5
Sol :
n

Q-17 The correct IUPAC name of D-Glucose is : CHO (D-Glucose)

H OH

HO H

H OH

H OH

Soln:

Q-18 The Fisher projection of the molecule as represented in the wedge dash is.
Br Br

H 5C 2 CH3
H 5C 2
CH3
H H

Soln:

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 33 ISOMERISM

Q-19 The correct configuration assigned for compound (I) & (II) respectively are :
COOH CH3

H CH3 C
COOCH3
COOCH 3 HOOC
(I) H
Soln: (II)

Q-20 Total number of stereoisomers of compound is :

CH3  CH  CH  CH3
| |
OH Br
Soln:

Q-21 Which side is favoured at equilibrium, provide quantitative explanation :

O O O O
H 2 O 
 + HO–
O O O O
pK a  16 pKa =13
Soln:

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CHEMISTRY 34
Q-22 (+) 2-butanol has specific rotation of + 13.9° when measured in pure form. A sample
of 2-butanol was found to have an optical rotation of –3°. What is the stereomeric composition
of this mixture ?
Soln:

Q-23 Discuss the optical activity of tertiary amines of the type R1R2R3N :
Sol :
n

Q-24 Draw the enantiomer of the following structure :

CH3

H C
Cl C2H5
Soln:

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 35 ISOMERISM

Q-25 Assign R and S configuration to the chiral carbons in the following :

CH3 CH3
HO···H H···OH
(i) (ii)
H···OH H···OH
CH3 CH3

Soln:

Q-26 An organic molecule necessarity shows optical activitiy if it :

(A) Contains asymmetric carbon atoms
(B) is non polar
(C) is non superimposable on its mirror image
(D) is superimposable on its mirror image
Soln:

Q-27 Ordinary light can be converted into plane polarized light with the help of a :
(A) Nickel prism (B) Nicol prism
(C) Diffraction grating (D) Quartz cell
Soln:

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CHEMISTRY 36
Q-28 The structure shows :
(A) Geometrical isomerism H3C H
C=C H
(B) Optical isomerism H3C C
COOH
(C) Geometrical & optical isomerism CH3
(D) tautomerism
Soln:

Q-29 How many optically active stereoisomers are possible for butane –2,3–diol :
(A) 1 (B) 2 (C) 3 (D) 4
Sol :
n

Q-30 The number of possible enantiomeric pairs that can be produced during monochlorination
of 2–methyl butane is :
(A) 2 (B) 3 (C) 4 (D) 1
Sol :
n

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 37 ISOMERISM

Q-31 Rotation of polarised light can be measured by :

(A) Monometer (B) Galvanometer (C) Polarimeter (D) Viscometer
Soln:

Q-32 The optically active tartaric acid is named as D–(+) tartaric acid because it has a positive :
(A) optical rotation and is derived from D–glucose

(B) pH in an organic solvent

(C) optical rotation and is derived from D–(+)– glyceraldehyde

(D) optical rotation only when substituted by deuterium

Sol :
n

Q-33 The enol form of acetone, after treatment with D 2O gives

OD O OH OH
(A) CH3–C=CH2 (B) CD3–C–CD3 (C) CH2–C=CH2D (D) CD2=C–CD3

Soln:

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CHEMISTRY 38
Q-34 The number of isomers for the compound with molecular formula C 2BrCIFI is :
(A) 3 (B) 4 (C) 5 (D) 6
Soln:

Q-35 Hydrogen of the following compound in the presence of poisoned palladium catalyst gives :
(A) optically active compound
Me H Me
(B) an optically inactive compound
(C) a racemic mixture H
(D) a diastereomeric mixture Me H

Soln:

Q-36 Statement-I : Molecules that are not superimposable on their mirror images are chiral
Because
Statement-II : All chiral molecules have chiral centres.
(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.
Soln:

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 39 ISOMERISM

Q-37 The correct statement(s) concerning the structures E, F and G is (are)

H3C O H3C OH
H3C CH3
H3C CH3 H3C CH3 H3C OH
(E) (F) (G)

(A) E, F and G are resonance structures

(B) E, F and E, G are tautomers
(C) F and G are geometrical isomers
(D) F and G are diastereomers
Soln:

Q-38 The correct statement(s) about the compound given below is (are) :-
(A) The compound is optically active Cl H
(B) The compound possesses centre of symmetry
H3C CH3
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry Cl H
Soln:

Q-39 The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3 (X) is (are) :
(A) The total number of stereoisomers possible for X is 6
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers
possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible
for X is 2
Soln:

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CHEMISTRY 40
Q-40 P & Q are isomers of dicarboxylic acid C 4H4O4. Both decolorize Br2/H2O, On heating P forms the
cyclic anhydride.
Upon treatment with dilute alkaline KMnO 4, P as well as Q could produce one or more than one
from S, T and U.
COOH COOH COOH
H OH H OH HO H
H OH HO H H OH
COOH COOH COOH
(S) (T) (U)
. Compounds formed from P and Q are respectively
(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
Soln:

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 41 ISOMERISM

ABHYAAS - V
LEVEL - II

Q-1 Write the newman projection formula along C1–C2 bonds in staggered form of following compounds.
1 2 1 2
(I) CH3–CH2–CH3 (II) CH3–CH–CH3
CH3
CH3 CH3 CH3
1 2
(III) (IV) CH –CH–CH–CH
3 3
1 2
CH3
Soln:

Q-2 Write the newman projection formula of the following compounds

(I) Cl–CH2–CH2–CH3 in its most polar form.
(II) Cl–CH2–CH2–Cl in its most stable form.
(III) HO–CH2–CH2–OH in its most stable form.
(IV) HOOC–CH2–CH2–COOH in its least stable staggered form.

Soln:

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CHEMISTRY 42
Q-3 Convert the following Fischer projection into Newmann & Sawhorse projection
COOH CH3

(A) H OH (B) H OH

H OH HO H

COOH CH3

Soln:

Q-4 Which conformational state of n-butane lies in higher energy state when rotated along C2 – C3 bond ?

Soln:

Q-5 Write down the C2–C3 bond, and draw Newman projection formula for the most stable conformation of
2,2–dimethylbutane
Soln:

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 43 ISOMERISM

Q-6 The two structures I & II represents :

C H3 CH3
H H H
H

H3C H
H3C C H3 CH3
H
(I) (II)
Constitutional isomers

Soln:

Q-7 Which of the Newman projections shown below represents the conformation about the C 1–C2
bond of 1 Bromo –2–methylpropane?
CH3 C H3 C H3 C H3
H CH3 Br H Br C H3
H Br
(A) Br (B) (C) (D)
H H H H C H3 H H
H C H3 H C H3

Soln:

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CHEMISTRY 44
Q-8 Which point on the potential energy diagram is represented by Newman projection shown here ?
H
H H

H3C H
C H3
Soln:

Q-9 Which statement is correct about anti conformation of 1-Chloropropane ?

(A) It is the most polar form (B) It has maximum torsional strain
(C) It has minimum steric strain (D) A and C both
Soln:

Q-10 Which of the following is correct P.E. diagram for propane ?

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

Soln:

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 45 ISOMERISM

Q-11 Identify whether the stereogenic centre is present or not :

(i) 2-Cyclo penten-1-ol (ii) 3-cyclo penten-1-ol
(iii) 2-bromopentane (iii) 3-bromopentane
Soln:

Q-12 Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is-
(A) 2-methyl pentane (B) 2,2–dimethyl butane
(C) 2,3–dimethyl butane (D) n-hexane

Soln:

Q-13 Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche)
of 2-fluoroethanol is
(A) Gauche, Eclipse, Anti (B) Eclipse, Anti, Gauche
(C) Anti, Gauche, Eclipse (D) Eclipse, Gauche, Anti
Sol :
n

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CHEMISTRY 46
Q-14 Which one of the following conformations of cyclohexane is chiral ?
(A) Twist boat (B) Rigid (C) Chair (D) Boat
Sol :
n

Q-15 How many chiral compounds are possible on monochlorination of 2–methyl butane ?
(A) 6 (B) 8 (C) 2 (D) 4
Soln:

Q-16 Which branched chain isomer of the hydrocarbon with molecular mass 72 u gives only one isomer
of mono substituted alkyl halide ?
(A) Neohexane (B) Tertiary butyl chloride
(D) Neopentane (D) Isohexane

Soln:

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 47 ISOMERISM

Q-17 Isomers which can be interconverted through rotation around of single bond are -
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers
Sol :
n

Q-18 If C 2 in below compound is rotated by 120º angle in anticlockwise direction along C 2 –C 3 ,

which of the following form will be produced : 1
(A) Partial eclipsed CH3
H H
(B) Perfectly eclipsed
2
(C) Perfectly staggered 3
(D) Gauche conformation
H H
Soln: CH3
4

CH3
Cl2/hv Fractional distillation
Q-19 CH3–CH–CH2–CH3 N (no. of isomers)   (F), (N) and (F) are :


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

Sol :
n

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Q-20 In the Newman projection for 2,2–dimethylbutane X and Y can respectively be –
(A) H and H X
(B) H and C2H5 H3C CH3
(C) C2H5 and H
(D) CH3 and CH3
H H
Sol :
n Y

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 49 ISOMERISM

ANSWERS
ABHYAAS-I

Q-1 (i) (ii) (iii)

(iv) (v)

Q-2 CH2 = C = CH – CH2 – C À C – CH2 – NH2

3 3
sp
2
sp sp2 sp sp sp sp

Q-3 H2C = C = CH2 (M.W. = 40)

Q-4 Metamerism

Q-5
CH3

OH
O O
Q-6 , ,

Q-7 H – C  C – H, Mol wt. = 26

Q-8 (i) Chain Isomers (ii) Chain Isomers (iii) Chain Isomers

(iv) metamers (v) Functional isomers (vi) Homologs.

Br SO3H Br
2 3 6 1

Q-9 SO3H 1 4
SO3H 5
2
|

6 5 4 3
(I) Br Br SO3H
(II)
Q-10 Aldehyde and Ketone are functional isomers.

Q-11 H3C CH3

C C
H3C CH3
C

H3C CH3

This structures has 1º H-atoms and all are identical.

Q-12
It has only six carbon atoms.

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Cl
Cl Cl

Q-13

Cl

first compound has 1, 4 position while second has 1, 3.

Q-14

Q-15 Ester – C – O – has different alkyl groups in I and II compound.

Q-16 Different C skeleton across the ester functional group.

Q-17 Molecular weight is different

Q-18 Only this (CH 3)3COH compound has same molecular formula with diethylether.

Q-19 CH3–CH2–CH3

CH 2 – CH – CH 2 Cl
| | | CH – CH – CH3
Cl
Cl Cl Cl Cl

Cl Cl
| |
Cl
Cl – C – CH 2 – CH 3 CH 2 – C – CH 3 CH2 – CH2 – CH
| | | Cl
Cl
Cl Cl Cl

Q-20 Self explanatory.

Q-21 There are 7—1-butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, diethyl ether,
methyl propyl ether, and methylisopropyl ether.

Q-23 (A)

Q-24 (B)

Q-25 (C)

Q-26 Match the Column:

(A)-p; (B)-r; (C)-q; (D)-r,s

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ABHYAAS-II
Q-1 (ABC)
OH
|
Q-2 (i) CH 2  CH  NH 2 (ii) CH 2  C  CH 3

O H O
H O O O O H
OH
(iii) CH  C  N (iv) 



3
CH 3 CH 3
O H H

Q-3 In Monocarbonyl compounds the keto form is more stable as C = O has more bond energy hence it is
thermodynamically more stable.

Q-4 (ABD)
Q-5 (D)
Q-6 (BCD)

Q-7 Maleic acid forms an anhydride where as fumaric acid does not.
O

CO2H H C H CO2H
CH
 O 

CH
H


 H H


 no anhydride.
C
CO2H CO2H H
O
Q-8 Lone pair - p conjugation between fluorine and carbon will be more effective than between
chlorine and carbon.
Q-9 a & b are tautomers and a & c are resonating structures.

Q-10 (A)

Q-11 (B)

Q-12 (ABC)
ABHYAAS-III
Q-1 (C) I, II & III are metamers because functional group is diester & there is only change in alkyl
group attachment.

Q-2 Only one which is .

Q-3 (I) 4 (II) 2

Q-4 Only one which is .

Q.5 4

Q.6 3

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CHEMISTRY 52
H
N–OH N–OH
+ 
NH 2 OH
 + (syn + anti)
O (1) H (2)

Q-7 (i) = E (ii) = E (iii) = E (iv) = Z

Q-8 Geometrical isomers have different spatial arrangement.

Q-9 Acyclic compounds along s-bond donot have restrised roation.

Q-10 Follow conditions of geometrical isomerism.

Q-11 Follow conditions of geometrical isomerism.

Q.12 Follow conditions of geometrical isomerism II & IV.

Q-13 (C) E-isomers have senior groups on anti-orientation.

C6H5 1 2 H
C=C 3 4
Q-14 H CH – CH3 trans-3-chloro-1-phenyl but-1-ene.
|
Cl
Q-15 Follow conditions of geometrical isomerism.

Q-16 Unsymmetrical compound with 3 stereocentres has 8 stereoisomers.

Q-17 Symmetrical compound with 2 stereocentres has 3 stereoisomers. [2n – 1 + 2(n – 2)/2]

Q-18 Unsymmetrical compound with 2 stereocentres has 4 stereoisomers.

Q-19 (D) Z-isomers have senior groups on same side.

Q-20 (A) Follow conditions of geometrical isomerism.

Q-21 Match the column:

(A) q ; B p ; (C)  r ; (D) s

Q-22 If the bonds were localized, there would be 4 isomers ; actually there are only 3 of the following,
the first two are identical, because the bods are not localized.

Cl Cl Cl Cl
Cl Cl

Cl
Cl
Q-23 Only CHBr = CHCl can exist as geometric isomers :
Br Cl Br H
C C and C C
H H H Cl
In CH2Cl— CH2Cl and CH2Cl—CH2Br, the carbon atoms are connected by a single bond about
which the groups can rotate relatively freely. Thus any conformation of the halogen atoms may be
converted into any other simply by rotation about the single bond. In CH 2Cl2, the configuration of
the molecule is tetrahedral and all interchanges of atoms yield exactly equivalent configurations.

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H H
Q-24 This is cis form. Two H atoms on the same side. To get trans, ring must be twisted.

Double bond becomes severely twisted-destabilized. Effective overlap of P orbitals is missing,

so does not exist.

Q-25 The P z orbitals forming -bonds and the empty P z orbital of the carbon with +ve charge are
parallel. So the electrons may be delocalized. The +ve charge is effectively spread out over
two carbons; delocalized.
-orbital
H empty orbital
C C
H C+ H
H
 
CH2=CH— C H 2  C H 2 —CH= CH

In n-propyl cation, + I effect of R increases the stability.

In allyl + M effect increases the stability. But + M effect in allyl cation is more effective. So allyl > propyl.
A group with + M effect stabilizes cation; destabilizes anion.
:

CH2 =CH · NH·CH3

Q-26

:

CH2 ·CH = NH·CH3 (this shows Geometrical isomerism)

Q-28 (C) Q-29 (A) Q-30 (C) Q-31 (A) Q-32 (D) Q-33 (B) Q-34 (A)

ABHYAAS-IV

Q-1 (I) Plane of symmetry and Centre of symmetry.

(II) Plane of symmetry.
(III) Plane of symmetry.
(IV) Plane of symmetry.
(V) Plane of symmetry and Centre of symmetry.
(VI) Centre of symmetry.

Q-2 (I) 1 (II) 2 (III) 3 (IV) 5

Q-3 (I) Enantiomers (II) Positional isomers (III) Identical (IV) Diastereomers

OH
Q-4 H C2 H5
H CH3
OH

Q-5 There is change in C skeleton across the functional group. - Metamerism

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Q-6 This structure has plane of symmetry across 1-3 but there is no centre of symmetry..

 * 
 CH 3 – C H – C 2 H 5 
Q-7 Butan-2-ol  |  is the least molecular weight alcohol which is optically active.
 
 OH 
 

H 3C CH3
1

Q-8 has no chiral centres and it has plane of symmetry across C1 – C4.
4
H Cl

Q-9 Only III has chiral centre and disymmetry.

Q-10 X has 0 chiral centres.
Y has 2 and Z has only one chiral centres.
Q-11 Polarimeter
* * *
Q-12 CH3 – C H – CH2 – C H – C H – CH3 has three chiral carbons.
| | |
OH Br C 2H5

CH3 3

Q-13 1 Br OH 2 the arrow is anticlockwise and least priority group is on the bottom ofline
H
in vertical fischer-projection.
CH3 1 1
3 CH2OH CH3
2 2
Q-14 NH2 2 H H NH2 Q-15 H OH (2S, 3R)
1
CH2OH 3
CH3 H 3 NH2
'D' CH3
4

CH3
HO H
Q-16 (2R, 3R) -3-chloropentan-2-ol
H Cl
C 2H 5

Q-17 When –OH is present in right side of horizontal line & high priority at the top than it is consider as
D & if left side then L.

Q-18 First decide the (R/S) configuration in wedge-dash and then draw fischer projection with equivalent
configuration.

COOH CH3

Q-19 H CH3 C
COOCH3
COOCH 3 HOOC
(S) H
(R)

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Q-20 Unsymmetrical compound with 2 chiral centres has 22 = 4 stereoisomers.

Q-22 Let x is the % of (+) 2-butanol.
13.9 x – 13.9 (100 – x) = – 300.
x = 39.2, % of d form = 39.2, % of  form = 60.8.
••

Q-23 Tertiary amines have pyramideal geometry with sp3-hybridization at nitrogen. N

R1 R3
It should be a chiral molecule (assuming lone pair to be a substituent). Thus,
R2
tertiary amines exist as racemic mixture but they cannot be resolved.
This is due to the reason that the energy difference between the isomer is very small (25 kJ mol –1).
Hence, rapid nitrogen or amine inversion takes palce.
2
sp -hybridized 2
2
R1 sp
R1 sp R1
R2 N R2

••
N

•
N
R3 •• R3
R2 R3
Planar transition state
Enantiomers
Tertiary amine N-oxide has four group hence nitrogen inversion is not possible, thus tertiary
amine -N-oxide can be resolved.

CH3

Q-24 Cl C
H C2H5

Q-25 (i) 2R, 3R (ii) 2S, 3R

Q-26 (C) Q-27 (B) Q-28 (B) Q-29 (B) Q-30 (A) Q-31 (C) Q-32 (C)

Q-33 (A) Q-34 (D) Q-35 (B) Q-36 (C) Q-37 (BCD) Q-38 (AD)

Q-39 (AD) Q-40 (B)

ABHYAAS-V
H H
H CH3 H3C CH3
Q-1 (I) (II)

H H H H
H H

Cl Cl
H H H H
Q-2 (I) (II)
H H H H
CH3 Cl

O–H COOH
H O–H H H
(III) (IV)
H H H H
H COOH

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Q-3 Newmann Sawhorse
COOH COOH

H OH OH
H H
(A) HO
HO H COOH
COOH

CH3 CH3
H OH OH
H OH
(B) H
H OH
CH3
CH3

Q–4 Eclipsed
CH3
H H

Q-5
H 3C CH3
CH3

Q-6 Molecule have different IUPAC name/structures.

C H3
Br H
Q-7
H C H3
H

Q-8 Gauche form - Q.

Q-9 Anti conformation is stable & polarity is present in one directions.

Q-10 Self explanatory.

Q-11 (i) Hydroxyl bearing carbon is stereogenic centre.,

H OH

4=3 3=4

(ii) 5=2 2=5

It has no stereogenic centre.
H OH

Br

(iii) CH3·C·CH2·CH2·CH3 bromine bearing carbon is stereogenic centre.

H Br

(vi) CH3·CH2·CH·CH2·CH3 It has no stereogenic centre.

Q-12 (C) Q-13 (B) Q-14 (A) Q-15 (D) Q-16 (D) Q-17 (A) Q-18 (D)
Q-19 (B) Q-20 (BD)

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