Subjective Questions

(1) (2)

(3) (4)

(5) (6)

(7) O (8)

OH
OH OH OH

(9) (10)
10 Problems in Organic Chemistry

(C) Write the I.U.P.A.C. names of the following

(1) (2)

(3) (4)

(5) (CH3)3C(CH2)4COOH (6) CH3CH2 H ) CHBrCH2CH3

6 4
CH 2 — CH — CH—CH2COCl
(7) H3 6
H4)]2COOH (8) | | |
COCl COCl COCl

(9) (10)

(11) (12)

(13) (14) O
N

CH3

(15) (16) CH3 – O – CH2 – CH2 – CH2OH

(17) (18)

(19) CH3 — CH OH CH Cl CO O CO CH OH CH3 2

(21) HCOOCHCHOHCH3 (22)

Nomenclature of Organic Compounds 11

(23) (24)

(25) —— H

(26) CH3— CO — CH = CH — C — CH — CH = CH — CONH2

O OH

(27) CH3 — CH = C H — — (CH = CH)2 — COOH (28) (CH2 = CH)4C

(29) (30)

Multiple Choice Questions

1.

2.

3.

4. Me2CCl CH2

5.

6. I.U.P.A.C. name of
12 Problems in Organic Chemistry

7.

(a)

8.

9. I.U.P.A.C name of

10.

O
11. I.U.P.A.C. name of
O O

12. I.U.P.A.C. name of

13. 3

14. I.U.P.A.C name of I

Br

15.
Nomenclature of Organic Compounds 13

16. I.U.P.A.C name of

17. I.U.P.A.C. name of

18. I.U.P.A.C name of CH3—CH—C—CH—COOH

| || |
OH O CONH2

19.

20. I.U.P.A.C. name of

21. I.U.P.A.C name of

22. 3

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

23. CH2 — CH = CH2

24. I.U.P.A.C. name of

14 Problems in Organic Chemistry

25.

(a)

O CH2Br
Cl
O

26.
(a) (CH2 = CH — = CHCO)2 2
= — CH = CHCO)2O

2
= CH — CH = CH COO CO CH = — CH = CH2
27. CH3CH2—CH—CH—CHO
|| |
O CN

28. CH3CO CH (CH3CO) COOCH3

Bu
|
29. I.U.P.A.C name of Pr—C—Ac
|
Et

30.

(a)

31.

32.
Nomenclature of Organic Compounds 15

33.
(Compound) (IUPAC name)

(a)

Ethane

OH
Phenol

34. I.U.P.A.C name of H2N — N CO2H

35.
2 2

36. 3

37. I.U.P.A.C name of

(a) 2,2/ /

/ /

38.

39.
(a) 4p p p p

40. I.U.P.A.C name of

16 Problems in Organic Chemistry

41.

42.

43. I.U.P.A.C name of

44.

45. HCOOCHBrCH2

46.

47.

48.

49.

50.
 Main Features

1. If two compounds have same molecular formula but different structural formulae or physical or chemical properties then they
are called isomers and the phenomenon of their existence is called isomerism. Isomerism is of two types (i) Structural isomerism
(ii) Stereo isomerism
2. Structural isomerism: In it the two isomers have different arrangement of atoms with in the molecule. Structural isomerism
is of the following types
Chain isomerism (or skeleton isomerism) These isomers have same positions of multiple bond & functional group but differ
from one another in the length of parent ‘C’ chain
CH3 — CH2 — CH2 — CH2 — OH

n – Butyl alcohol (4C) Isobutyl alcohol (3C)

Position isomerism: These isomers have same length of ‘C’ chain but differ from one another in the position of multiple bonds,
branch or functional group.
CH2 CH — CH2 — CH2 — CH3 and CH3 — CH CH — CH2 — CH3

3. Functional isomerism: These isomers have different functional groups i.e. isomers belong to different homologues series.
> CH3CH2CHO & CH3COCH3 & CH2 = CH — CH2OH
(Aldehyde) (Ketone) (Alcohol)
> CH3CH2CN & CH3CH2NC CH3CH2OH & CH3OCH3
> CH3COOH & HCOOCH3
> Ring chain isomerism is also an example of functional isomerism. For example n-butene & cylobutane, butyne & cyclo butene
Metamerism: It is due to the difference in the nature of alkyl groups attached to the same functional group.
CH3 — O — CH2CH2CH3 & CH3CH2OCH2CH3
Methyl propyl ether Di ethyl ether
Tautomerism: This type of isomerism has two functional isomers present in dynamic equilibrium.

% enol content ∝ 1/ Temperature ∝ conjugation ∝ H – bonding ∝ aromatic character

% enol content in decreasing order is as follows.
20 Problems in Organic Chemistry

> PhCOCH2COCH3 > MeCOCH2COMe > MeCOCH2COOC2H5 > MeCOCH2COO Et > MeCOCH2COOMe
> MeCOCH3
4. Stereo isomerism: When isomers have the same structural formula but differ in relative arrangement of atoms or groups in
space within the molecule, these are known as stereoisomer and phenomenon of their existence is called stereoisomerism. Ste-
reoisomerism is of two types.
(a) Geometrical isomerism: Here the isomers differ in spatial arrangements of atoms or groups around the double bonded
carbon atoms.

> Calculation of geometrical isomers:

Alkene R1(CH = CH)n R2 Geometrical isomers
(1) When n = 1 or R1 = R2 2n
n
–1
n –1 2
(2) When R1 = R2, n = even 2 +2
( n + 1)
–1
(3) When R1 = R2, n = odd 2n – 1 + 2 2

> Geometrical isomers possess different physical properties. Their chemical properties are similar but not identical.
> Due to good packing of trans isomers, it has higher melting point than cis isomer
(b) Optical Isomerism (Enantiomerism):
> The isomer which does not rotate the plane of ppl is called optically inactive and which rotates the plane of ppl is
called optically active. The isomer which rotate the ppl towards left is known as laevo (l) while which rotates the ppl
to right is known as dextro (d).d & l isomers are non super imposable mirror images of each other & are known as
enantiomers The optical isomers which do not have mirror image relationship are called diastereomers
> Equimolar mixture of d & l isomers of a same compound is called dl or (+) or racemic mixture.
> Calculation of optical isomers:
(i) Compounds which have unsymmetrical molecule with one or more chiral centres. In such compounds if n is the
number of chiral carbons, then
Optically active forms = 2n, Enantiomeric pair = 2n / 2
Optically inactive form = 0
1 n –1
(ii) If it is symmetrical & n = even then optically active forms = 2n–1 enantiomeric pair = (2 )
2
n –1
Optically inactive forms = 2 2
(iii) If is symmetrical & n = odd then
n –1
n –1
Optically active forms = 2 – 2 2 = a (say)

n –1
Enantiomeric pair = a/2, Optically inactive form = 2
2
LEVEL – I

Subjective Questions
1. Draw the Fischer projections of the following.

(a) (b) (c)

Isomerism 21

(d) (e) (f)

CH3
D OH
(g) (h) H CO (i)
H
NH NH2

( j)

2. In Q.no.1 which is / are meso forms?

3. Assign the names R or S to the following.

(a) (b) (c)

Cl

(d) (e) (f) O

O
CH2I

(g) (h) (i)

Cl

(j) H CH2OD (k) (l)

(m) (n) (o)

22 Problems in Organic Chemistry

4. Assign the names E & Z to the following.

(a) (b) (c)

Cl—CH2 CH2CCl3
C
(d) (e) CH2COCH3 (f)
C
NHCOCH3 Br CH3

HOH2C CH2CN
(g) (h) C C (i)
OHC CH2CH2NH2
HOH2C CH2CN
( j) C C
OHC CH2CH2NH2

Multiple Choice Questions

1. Which among the following can show both the stereoisomerisms i.e. optical & geometrical?

(a) (b) (c) (d)

2. What is the relation between the following three structures?

(a) 1 & 2 are enantiomers (b) 2 & 3 are enantiomers

(c) 2 & 3 are structural isomers (d) 1 & 2 are homomers

3. I.U.P.A.C name of

(a) 2 – Chloro cyclohexan-1-ol (b) 1 D-Chloro cyclohexane-2D-ol

(c) 1-Chloro cyclohexane-2-ol (d) 2D-Chloro cyclohexan-1L-ol
4. D – form of the compound PhCHOHCH3 can be written as:-

(a) (b) (c) (d)

Isomerism 23

5. Optical rotation of the following isomer is + 36°

Which isomer will have the optical rotation equal to-36°?

(a) (b) (c) (d)

6. Consider the following compounds:-

(1) CH3NO2 (2) (3) (4)

The compounds which can also exist in its enol form is / are:-
(a) 1 (b) none (c) all (d) 1 & 3

7. How many geometrical isomers are possible for CH3 (CH = CH)3 CH3
(a) 4 (b) 5 (c) 6 (d) 8

8. How may geometrical isomers are possible for CH3(CH = CH)3C2H5

(a) 4 (b) 5 (c) 6 (d) 8
9. An optically active compound is placed in a polarimeter tube of length 5 dm & rotates ppl by 60°. If 40 gm compound is

is diluted up to 2 lit.
(a) 60° and 12° (b) 60° and 6° (c) 30° and 12° (d) 30° and 6°

10. In which isomer plane of symmetry is present

Br

Cl H

H
(a) (b) (c) (d) OH OH

H Cl

H H
COBr

COCH3
11. F This is:-
Br

(a) R, Z (b) S, Z (c) S, E (d) R, E

24 Problems in Organic Chemistry

12. The structures shown below can be related as:

(a) Position isomers (b) Diastereomers (c) Enantiomers (d) Homomers

13. Identify the meso isomer

(a) (b) (c) (d)

14. and are:-

(a) Chain isomers (b) Positional isomers (c) Functional isomers (d) All of these
15. Which is highly stable?

(a) (b) (c) (d)

16. The number of cis–trans isomers possible for the following compound are:

(a) 8 (b) 4 (c) 2 (d) 16

17.

(a) I & II are diastereomers (b) I & III are diastereomers

(c) I, II & III, I are enantiomers (d) II & III are enantiomers
Isomerism 25

18.
(–)-2-chloro butane which has rotation of 7.2° would be.
(a) 49.66% (b) 50% (c) 18.5% (d) 83.9%
19. Which is optically active?

(a) (b) (c) (d)

20. Identify the species which is optically active.

(a) (b) (c) (d) NH2Cl

21.

CHO
HO H
(a) (b) (c) (d)
H OH
CH2OH

22.
25% retention.
(a) +36° (b) +9° (c) +27° (d) Zero

23. AcCH2COOEt, AcCH2CO2Me, PhCOCH2Ac

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

Decreasing order of % enol content in the given compounds is:-
(a) I > II > III > IV (b) I > III > II > IV (c) I > IV > II > III (d) I > II > IV > III
24. How many steroisomers are possible for the following?

(a) 8 (b) 6 (c) 2 (d) 4

25. Total number of cyclic structural as well as stereo isomers possible for a compound with the formula C5H10 is:
(a) 5 (b) 7 (c) 10 (d) 6
26. Arrange the following compounds in decreasing order of heat of hydrogenation.

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

(a) I > II > III > IV (b) IV > III > II > I (c) IV > I > III > II (d) IV > III > I > II
26 Problems in Organic Chemistry

27. If stereochemistry about the double bond in the compound shown below is cis, the number of enantiomers possible for this
compound would be:
CH2BrCH – CH = CH CHBr – CH3
(a) 2 (b) 4 (c) 6 (d) 8

28. The structures given below are and

(a) Enantiomers (b) Conformational enantiomers (c) Rotamers (d) Geometrical isomers
29. How many optically active isomers are possible for CH3(CHCl)3CH3
(a) 2 (b) 3 (c) 8 (d) 6
30. How many meso forms are possible for CH3(CHCl)4C2H5
(a) 2 (b) 3 (c) 1 (d) Zero
31. Which statement is wrong for the given compound?

32. In which solvent % enol content of CH3 CO CH2 COCH3 will be least:
(a) Benzene (b) H2O (c) D2O (d) Hexane

Passage - 1

Multiple bonds do not possess free rotation. The isomerism generated due to restricted rotation is called geometrical isomerism.
The isomer in which similar groups are on the same side of multiple bonds is called cis & isomer in which similar groups are on
the opposite side of double bond is called Trans isomer. In case of C = N & N = N Multiple bond the designation cis & Trans are
replaced by Syn & Anti respectively.
Answer the questions from 33 to 37
33. Which is Syn ethyl phenyl ketone oxime?
CH3CH2 OH
C
(a) (b) (c) (d)
N
Ph

34. Which does not contain centre of symmetry?

(a) (b) (c) (d) (b) and (c)

Isomerism 27

35. Which will not exhibit geometrical isomerism?

CH3
(a) C CHCH3 (b) (c) Ph2N2 (d)
Et
36. Which is cis isomer?

(a) (b)

(c) (d) All of these

37. Which is more stable:-

Cl
(a) Cl Cl (b)

Cl
Cl Cl

(c) (d)

Cl
Cl

Passage II

Some times isomer does not contain chiral carbon atom but it shows optical isomerism. It is due to the presence of chiral plane.
Biphenyls and cumulenes exhibit this type of optical isomerism. Cumulenes are those unsaturated hydrocarbons which contains
consecutive double bonds.
If cumulene contains odd no. of double bond it is always optically inactive and in case of even number of double bonds it shows
optical isomerism only when it is asymmetrically substituted.
Answer the questions from 38 to 40.
38. Which is optically active:-

(a) CH3CHClCH3 (b)

(c) (d)
28 Problems in Organic Chemistry

39. Which is resolvable?

(a) (P — CH3C6H4) CH = C = CHCH3 (b) CHCl = C = CH2

(c) (d) Threo tartaric acid

40. Which does not contain plane of symmetry:-

(a) (b)

(c) (d)

Passage III

does not change on rotation but changes only when bond breaks & forms in new direction. If two exchanges are made in an isomer

Answer the questions from 41 to 43.

CH3 D OH

41. (I) (II) (III) H CO (IV) H NH2

NH

Which statement is correct?

(a) I & II are same (b) I & IV are same
(c) II & III are same (d) III & I are same

42. is similar to:-

Cl
Cl Cl Cl

Cl
(a) (b) (c) (d)
Cl
Cl
Cl

43. Which statement is false for isomers?

(a) They have same molecular formulae (b) They have same vapour density
(c) They have same empirical formulae (d) All are correct
Isomerism 29

44. Which pair of isomerism is not possible together?

(a) Functional and position (b) Ring chain & functional
(c) Metamerism & functional (d) Chain & functional
45. Decreasing order of % enol content of the following compounds would be:

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

(a) 2 > 3 > 4 > 1 (b) 2 > 1 > 3 > 4 (c) 4 > 1 > 3 > 2 (d) 2 > 1 > 4 > 3
46. Which is not erythro?

(a) Meso tartaric acid (b) (c) (d)

Ph
H Me
47. HO2C CO2H 
→ A & B. Which of the following statement is true?
H Me
Ph
(a) A & B are structural isomers. (b) A & B are enantiomers
(c) A & B are geometrical isomers (d) A & B are diastereomers

aq
48. ¾¾¾ ® +
NaOH

This reaction is leading to % racemisation

(a) 40% (b) 60% (c) 80% (d) 20%

49. (1) (2) (3) CH3CH2CH2COONa (4)

Resolvable compound is / are:-

(a) Only 2 (b) 1, 2 & 3 (c) Only 4 (d) 2 & 4
50. Largest % enol content will be found in:-
O

O
(a) (b) (c) (d)
30 Problems in Organic Chemistry

51. The wrong statement concerning the structure A, B & C is:

O
Et Ph Ph

Ph Et OH CH3 OCH3

(a) (b) (c)

(a) A & C are functional isomers (b) B & C can show geometrical isomerism
(c) A & B are tautomers (d) Degree of unsaturations of A, B & C are not same
52. The priority sequence for the group CH3 , C14 H3 , D & H will be in the order
(1) (2) (3) (4)

(a) 3 > 2 > 1 > 4 (b) 3 > 4 > 1 > 2 (c) 2 > 3 > 1 > 4 (d) 2 > 1 > 3 > 4
53. Alternating axis of symmetry is not present in:
D
Cl
Cl NO2
CH3 H

(a) (b) H H (c) D (d)

F Br
CH3
Cl Cl
H

H
54. Maximum number of atoms present in one plane of the following isomers is:

H H
C=C=C=C
HS D

(a) 8 (b) 6 (c) 9 (d) 4

55. Optical isomerism will not be exhibited by:

O O
Br Br
(a) (b) (c) P (d) P
OMe OMe
D OMe Me

56. Which pair does not represent metamerism?

Me
Cl HO Me
(a) Ph—OCO & Ph—COO (b) &
Cl
OH

(c) CH3CH2NH2 & CH3NHCH3 (d) &

57. How many structural isomers are found to be optically active obtained by the mono chlorination of methyl cyclo butane:
(a) 1 (b) 2 (c) 3 (d) 4
58. Which will have least stable enol form?
O O O
O O

(a) O (b) (c) NO2 NO2 (d) I I

Isomerism 31

1
H

4
59. H O Which H will involve in keto - enol tautomerism?
H
O 3
H
2
(a) Only 1 (b) 2 & 4 (c) Both (d) none

Cl CMe2CMe2H
HO
60. C C C C
F CH3 CH2CH2CH3
ClO

(a) Z, Z (b) E, E (c) Z, E (d) E, Z

61. How many optically active isomers are possible for 1,3,5-tri methyl cyclohexane.
(a) 2 (b) 4 (c) 6 (d) none

NHCOMe O
OH
O
62. and are:-
H
Br
(a) RR (b) RS (c) SS (d) SR
63. Which will show enantiomerism?

Me Me Me Br Me
(a) O NH (b) (c) (d)

Br

64. If in an organic compound two COOH groups are present on same C atom then such a compound looses one molecule of carbon
dioxide on heating.
HOOC
3
NMe2 Heating
¾¾¾¾ ®X
HOOC 1 2
COOH
1
is:-
(a) R (b) S
(c) may be R or S (d) R & S names can not be assigned
65. The most stable form of 2 – nitro ethanol is:-

H NO2 NO2 H
H NO2 H H H OH H NO2
(a) (b) (c) (d)
H H H H H H H H
OH OH H OH
32 Problems in Organic Chemistry

66. The most stable form of 1, 2 – Di nitro ethane is:-

H NO2 NO2 H
H NO2 H NO2 H H H NO2
(a) (b) (c) (d)
NO2 H H H H NO2 H H
H H H NO2
67. The most stable form of cyclo hexane 1, 2-diol is:-
H
OH

OH
(a) (b) H
H
OH

OH H
OH H

(c) H (d) OH

H OH

OH H
68. The most stable form of 1, 2 di chloro cyclo hexane is:-
H
Cl

Cl
(a) (b) H
H
Cl

Cl
H
H
Cl
Cl
(c) (d) Cl
Cl
H

H
H
69. The most stable form of cyclo hexan – 1, 4 – di ol is:-
H
OH H
OH OH
(a) H (b) H

OH OH

OH H OH OH

(c) H (d) H H
Isomerism 33

70. The most stable form of 4 – Bromo cyclo hexanol is:-

Br OH

OH H
(a) Br (b) H

OH H
Br
(c) OH (d) H

Br

71. CH3CH2CH2CHO & CH3CH—CH3

|
CHO
(a) Metamers (b) Skeleton isomers (c) Position isomers (d) Homomers
72. Total number of aldehyde & ketone possible for C4H6O are: (Excluding stereo isomers)
(a) 10 (b) 6 (c) 8 (d) 7

73. and are:-

O Ac Ac O
H H

(a) Enantiomers (b) Geometrical isomers (c) Diastereomers (d) Position isomers
74. Which will have highest dipole moment?

D Cl H H
(a) (b) (c) (d)
D Cl H H H H Cl
H

75. How many stereo isomers are possible in A & B?

Br Br
(A) (B)

(a) 2 & 2 respectively (b) 2 & 4 respectively (c) 0 & 2 respectively (d) 0 & 4 respectively
76.

Cl 4
5 3

2 OH
1
CHO

(a) 1R 2R 5R (b) 1S 2R 5S (c) 1R 2S 5R (d) 1S 2S 5S

77. Which will have very small enol content?
O O
O O O
O NO2
(a) (b) (c) (d)
O
34 Problems in Organic Chemistry

( +) (–) ( +) (–)
!!⇀ CH 2 = N —O
78. CH3 — N — O ↽!!
|| |
O OH
(Nitromethane) (Aci-nitromethane)

Nitro methane is stable than aci – nitromethane because

(a) C = N bond is less stable than N = O bond.
(b) Hybridisation of ‘C’ changes from sp3 to sp2 which increases electro negativity of ‘C’
(c) Nitromethane is more stabilized by resonance than aci – nitro methane is not.
(d) Both are equally stable.
79. Maximum enol content is in:-

(a) (b) (c) CH3COCH2COCH3 (d) PhCOCH2COOCH3

80. Assertion -Conformers are not isolable at room temperature

Reason -These are unstable at room temperature
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
81. Assertion HDC = C = CHD can exhibit enantiomerism
Reason – It contains chiral carbon atom
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
82. Assertion - Me3C-NO2 can exhibit position isomerism but not tautomerism
Reason – Acidic hydrogen is absent in this compound
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
83. Assertion- HDC=C=C=CHD can exhibit optical isomerism
Reason- Entire molecule is planar
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
84. Assertion- Resolution of meso isomer in to two optically active forms is not possible
Reason- It contains plane of symmetry
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
Isomerism 35

85. Assertion: - % enol content in CH3CSCH3 is greater than that of CH3COCH3

Reason:-S—H bond is weaker than O—H bond because of large size of sulphur than oxygen.
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
86. Consider the following compound (A)

Assertion: - Compound A readily undergoes tautomerism

Reason: - Enol form of A is stabilized by H — bonding

(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
87. Consider the following three compounds

Assertion: - % enol contents of I, II & III vary from 100 to 80 & 1.4 respectively
Reason: - In this series H – Bond becomes longer and weaker
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true

88. Assertion: -

(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true
89. Assertion: - A mixture of cis & trans but – 2 – ene can be resolved at room temperature
Reason: - At room temp temperature cis transforms are not interconvertible
(a) Assertion is True, Reason is true: Reason is a correct explanation for assertion.
(b) Assertion is true Reason is true: Reason is not a correct explanation for assertion
(c) Assertion is True, Reason is False
(d) Assertion is False, Reason is true