INDEX

IIT JAM – ORGANIC PRACTICE BOOK

CHAPTER NO. CHAPTER NAME PAGE NO.

1 IUPAC & NOMENCLATURE 1

2 GOC & AROMATICITY 5

3 STEREOCHEMISTRY 27

4 INTERMEDIATE & NAME REACTION 46

5 REACTION MECHANISM 74

6 PROTECTION & DEPROTECTION 125

7 ORGANIC REAGENTS 170

8 PERICYCLIC 272

9 HETEROCYCLIC CHEMISTRY 294

10 ORGANIC SPECTROSCOPY 315

 CHAPTER
IUPAC & NOMENCLATURE
Multiple Choice Questions (MCQ)
1. Select the correct IUPAC Nomenclature of given 5. Give IUPAC name of the compound given below.
compound. Cl

COOH
O

OH
CHO (A) 2-Chooro-5-hydroxyhexane
(A) 4-Formyl-2-oxocyclohexane-1-carboxylic acid
(B) 2-Hydroxy-5-Chlorohexane
(B) 4-Carboxy-3-oxocyclohexane-1-carbanal
(C) 5-Chlorohexan-2-ol
(C) 2-Carboxy-5-Formyl-1-cyclohexanone
(D) 2-Chlorohexan-5-ol
(D) 2-Oxo-4-formyl-1-cyclohexanoic acid
6. IUPAC name of m-cresol is…
2. Select the correct IUPAC nomenclature for given
(A) 3-methylphenol
compound
(B) 3-chlorophenol
(C) 3-methoxyphenol
(D) benzene-1,3-diol
7. IUPAC name of the compound…
A B H
(A) A= 2,6,6-Trimethylbicyclo [3.1.1] hept-2-ene H3C C OCH3
B= Spiro [4.5] deca-1,6-diene
(B) A= 1,3,3-Trimethylbicyclo [3.1.1] hept-1-ene CH3
B= Spiro [4.5] deca-1,7-diene (A) 1-methoxy-1-methylethane
(C) A= 2,6,6-Trimethylbicyclo [1.1.3] hept-2-ene (B) 2-methoxy-2-methylethane
B= Spiro [5.4] deca-1,6-diene (C) 2-methoxypropane
(D) A= 1,3,3-Trimethylbicyclo [1.1.3] hept-1-ene (D) isopropylmethyl ether
B= Spiro [5.4] deca-1,7-diene 8. What is the IUPAC name for the compound shown below.
Cl
3. The IUPAC name of…
CH2OH

CHOH

Br
CH2OH
(A) .1-Bromo-3-chlorocyclohexene
(A) Propane-2,3-diol
(B) .2-Bromo-6-chlorocyclohex-1-ene
(B) Propane-1,2-diol
(C) .6-Bromo-2-chlorocyclohexene
(C) Propane-1,2,3-triol
(D) .3-Bromo-1-chlorocyclohex-1-ene
(D) Glycerol
9. The IUPAC name of the following compound is:
4. The IUPAC name of the compound
HOOC H
(A) 2-Chloro-3,4-dimethyl-n-pentyl alcohol
(B) 2-Chloro-3,4-dimethylpentan-1-ol
(C) 4-Chloro-2,3-dimethylpentan-1-ol
(D) 2,3-dimethyl-4-Chloropentan-1-ol
2 IIT JAM – Organic - Practice Book
(A) (R)-3- (but-6-enyl) hex-5-ynoic acid SOLUTIONS
(B) (S)-3- (prop-2-enyl) hept-6-ynoic acid 1. Sol. In naming molecules containing one or more of the
(C) (S)-3- (prop-2-ynyl) hept-6-enoic acid functional groups, the group highest priority is indicated by
(D) (R)-3- (prop-2-ynyl) hept-6-enoic acid suffix; the others are indicated by prefix.
10. The IUPAC name for the compound given below is:
OH

Ph

(A) (2R, 4Z)-7-phenylhept-4-en-2-ol

(B) (2S, 4Z)-7-phenylhept-4-en-2-ol
(C) (2R, 4E)-7-phenylhept-4-en-2-ol
(D) (2S, 4E)-7-phenylhept-4-en-2-ol
11. The IUPAC name of the compound given below is:
HO
OH
Functional group priority order is: Carboxylic acid >
Br Aldehyde >ketone
(A) (2E, 4E)-3-bromohexa-2, 4-diene-1, 6-diol Acid comes first so write Carboxylic acid suffix -oic acid.
(B) (2Z, 4E)-3-bromohexa-2, 4-diene-1, 6-diol Aldehyde prefix is formyl.
(C) (2Z, 4Z)-4-bromohexa-2, 4-diene-1, 6-diol Ketone prefix is oxo.
(D) (2E, 4Z)-4-bromohexa-2, 4-diene-1, 6-diol Write suffix at the end of IUPAC name.
12. The IUPAC name of the following compound is: So, numbering starts from acid, then write F.G
alphabetically.
COOH
1
6 O
2
(A) bicyclo [4.3.3] dodecane
5
(B) bicyclo [4.3.O] dodecane 4 3
(C) bicyclo [4.3.3] decane CHO
(D) bicyclo [4.3.3.O1,5] dodecane So, the correct option is a. 4-Formyl-2-oxocyclohexane-1-
13. IUPAC nomenclature of following compound is carboxylic acid

2. Sol.
2
3
2 1 4
(A) tricyclo [2.1.1.02,4] hexane 1 3 5
(B) tricyclo [0.1.1.22,4] hexane 10 6
6 4
(C) tricyclo [1.1.2.02,4] hexane 9 7
5 8
(D) tricyclo [2.1.1.01,3] hexane
A B
In bicyclic system numbering starts from bridgehead
ANSWER KEY
carbon, here at 2,6,6 position methyl groups. So, write
1 2 3 4 5 6 7 8 9 10
2,6,6-Trimethylbicyclo, after substituents write pair of
A A C C C A C D D C
square brackets with numerals denotes the number of
11 12 13
carbon atoms between each of the bridgehead atoms,
B A D here 3,1,1 carbon present. So, write square bracket
[3.1.1]. here 7 carbons with double bond at 2 position so
write hept-2-ene.

IFAS Publications
Chapter – 1 Iupac & Nomenclature 3
So, the correct name is A= 2,6,6-Trimethylbicyclo [3.1.1] 6. Sol.
hept-2-ene OH

Spiro compounds are named with the infix spiro followed 1

by square brackets containing the number of atoms in 6 2
smaller ring, then the number of atoms in the larger ring,
3
separated by a period, in each case excluding the 5
spiroatom itself. 4
Here, at 1 and 6 position double bond, so write 1,6 diene.
3-methylphenol
Here total carbons 10 therefore write deca.
Here functional group is phenol, So the numbering starts
So, the correct name is Spiro [4.5] deca-1,6-diene
from hydroxy group and substitent is methyl at 3
So, the correct option is a. A= 2,6,6-Trimethylbicyclo
position, so the name of compound is 3-methylphenol.
[3.1.1] hept-2-ene
So, the correct option is (a) 3-methylphenol
B= Spiro [4.5] deca-1,6-diene
7. Sol.
3. Sol.
1 2
1 H
CH2OH H3C C OCH3

2CHOH CH3
3
3 Here, at 2 position methoxy group and total 3 carbons, so
CH2OH
the name is 2-methoxypropane
Here functional group is alcohol.so, numbering starts
So, the correct option is (c) 2-methoxypropane
from functional group. Total carbons 3 so, the name is
propane & at 1,2,3 position hydroxy group, therefore
8. Sol.
write 1,2,3-triol.
Cl
So, the correct option is(c) Propane-1,2,3-triol
1
4. Sol.
6 2
5 4 3 2 1 3
5
H H H H2 Br
4
H 3C C C C C OH
Here, parent is cyclohexene and substituents is chlorine
Cl CH3 CH3 and bromine at 1 and 3 position, write the name of

Here functional group is alcohol, so the numbering starts from compound alphabetically so the name of compound is

the hydroxy group and substitent is chlorine at 4 position, so 3-Bromo-1-chlorocyclohex-1-ene

write the name of compound alphabeticaly. So, the correct option is (4).3-Bromo-1-chlorocyclohex-1-

So, the correct option is(c) 4-Chloro-2,3-dimethylpentan-1-ol ene

5. Sol. Here functional group is alcohol, so the lower 9. Sol. In naming molecules containing one or more of the

number to the hydroxy group and substitent is chlorine functional groups, the group highest priority is indicated by

at 5 position, so write the name of compound suffix; the others are indicated by prefix.

alphabeticaly.
Cl
3 1
5 4 2
6

OH
So, the correct option is((c) 5-Chlorohexan-2-ol

IFAS Publications
4 IIT JAM – Organic - Practice Book
Write suffix at the end of IUPAC name. 12. Sol. Here, bicyclic system therefore,write bicyclo first
then write a pair of bracket in between write number of
carbons present, at end write total carbon here 12
carbon therefore name is dodecane. So the name of
compound is bicyclo [4.3.3] dodecane
First select longest parent chain then write substituents, 13. Sol.
here 3 carbon is chiral, configuration is R, so write
configuration first then substituent, then highest priority
group suffix. Here, highest priority to alkene therefore
write suffix at the end of IUPAC name. therefore, IUPAC
name is R)-3- (prop-2-ynyl) hept-6-enoic acid
So, the correct option is (4) (R)-3- (prop-2-ynyl) hept-6-
enoic acid Here, tricyclic system therefore,write tricyclo first then
10. Sol. Here, 2 functional group alcohol and alkene, write a pair of bracket in between write number of
according to priority order higher order to the alcohol, so carbons present, at end write total carbon here 6 carbon
write suffix at end of name .In this compound at 4 therefore name is hexane. So the name of compound is
position double bond, hydrogens are on opposite site (4) tricyclo [2.1.1.01,3] hexane
therefore write E. Here 2nd carbon is chiral configuration
is R .So, the name of compound is (2R, 4E)-7-phenylhept-
4-en-2-ol

So, the correct option is(3) (2R, 4E)-7-phenylhept-4-en-2-

ol
11. Sol.
In this compound at 4 position double bond, hydrogens
are on opposite site therefore write E & at 2 position
double bond, same priority group are on same site
therefore write Z. So the name of compound is (2Z, 4E)-
3-bromohexa-2, 4-diene-1, 6-diol

So, the correct option is (2) (2Z, 4E)-3-bromohexa-2, 4-

diene-1, 6-diol

IFAS Publications
 CHAPTER
GOC & AROMATICITY
PART-1 (MCQ)
1. Inductive effect involves 8. Which of the following are resonating structures?
(A) Delocalisation of sigma electrons
(A) (B)
(B) Partial displacement of sigma electrons
(C) Delocalisation of π-electrons
(D) Displacement of lone pair of electrons (D)
(C) H3C-NO2 CH3-O NO
2. Select the correct statement about inductive effect
(A) Inductive effect is distance independent 9. Which of the following resonating structures is least
(B) Inductive effect creates net charge in the molecule stable?
(C) Inductive effect is polarization of sigma electrons O
O
(D) Transfer of electron takes place from one carbon to (A) (B)
another carbon
3. Resonance is
(A) Delocalization of π electrons
O O
(B) Delocalization of sigma electrons (C) (D)
(C) Delocalization of sigma-π electrons
(D) None of the above 10. The correct order of stability of the following resonating
4. Resonance involves structures is
(A) Delocalization of π-electrons along a conjugated
H-N=C=O H-N-C O H-N C-O
system 2
1 3
(B) Delocalization of lone pair along a conjugated system
(A) 1>2>3 (B) 2>1>3
(C) Delocalization of negative charge along a conjugated
(C) 3>1>2 (D) 1>3>2
system
11. The correct order of basic strength is
(D) All are correct
5. During delocalization which statement is incorrect C2H 5O- C2H5- C2H5NH- NH2- F-
(A) Net charge remains same 1 2 3 4 5
(B) Number of paired electrons remain same (A) 1>2>3>4>5 (B) 2>3>4>1>5
(C) Number of unpaired electrons remain same (C) 2>4>3>1>5 (D) 5>1>4>3>2
(D) Energy of resonating structure always remain same 12. The correct order of stability of the following resonating
6. Which of the following is the strongest -I group? structures is
+
(A) -N (Me)3
(B) -N+H3
(C) –F
(D) -OH
7. Which of the following pair is not resonating structures?

(A) (B) O O

(A) 1>2>3>4 (B) 3>4>2>1

H3C-C=O
(D) (C) 1=2=3=4 (D) 3=4>1=2
(C) CH3-C O
6 IIT JAM – Organic - Practice Book
13. The correct order of stability of the following resonating 19. Which of the following compounds has largest C=C bond
structures is length?

20. Correct order of dipole moment is

Cl Cl Cl
(A) 1>2>3>4 (B) 1>3>2>4 Me
(C) 1>4>3>2 (D) 4>3>2>1
14. Correct dipole moment order is Me
Me
Cl Cl Cl 1 2 3
Cl
(A) 1>2>3 (B) 2>3>1
(C) 3>1>2 (D) 3>2>1
Cl
Cl 21. Correct order of stability of the following alkene is
1 2 3
(A) 1>2>3 (B) 2>3>1
(C) 3>2>1 (D) 3>1>2 1 2 3
15. Which of the following cannot show resonance? (A) 1>2>3 (B) 2>3>1
(C) 3>2>1 (D) 3>1>2
22. Correct order of stability of the following alkene is

Me Me
1 2 3 4
(A) 2>4>1>3 (B) 2>3>1>4
(C) 2>4>3>1 (D) 2>1>3>4
16. Which of the following is aromatic hydrocarbon?
23. Select the correct order of base strength of the following
compounds

OH- CH3COO- Cl- F-

1 2 3 4
(A) 2>1>3>4 (B) 1>2>4>3
(C) 3>4>1>2 (D) 3>4>2>1
24. Which of the following alkene have maximum number of
17. Decreasing order of potential energy of the following
huperconjugating structures?
cation is

OH OH OH

N N N

1 2 3
(A) 1>2>3 (B) 2>1>3 25. Which will be the least stable resonating structure
(C) 2>3>1 (D) 3>2>1
18. The order of basicity of halide is
(A) I=<Br-<Cl-<F- (B) Cl=<F-<I-<Br-
(C) F=<I-<Br-<Cl- (D) Cl=<Br-<I-<F-

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Chapter – 2 GOC & Aromaticity 7
26. Select the correct order of heat of hydrogenation (A) 1>2>3 (B) 3>2>1
(C) 2>1>3 (D) 1>3>2

2
33. Among the following the aromatic compound is
1 3 4

(A) 4>3>2>1 (B) 1>2>3>4

(C) 2>3>4>1 (D) 4>1>2>3
27. Select the most basic compound
(A) Piperidine (B) Pyrrole
(C) Morpholine (D) Pyridine
28. The correct order of decreasing basicity in gas phase 34. Among the following non aromatic compound is

Me3N Me 2NH MeNH2 NH3

(A) (B)
1 2 3 4

(A) 1>2>3>4 (B) 2>1>3>4

(C) (D)
(C) 4>3>2>1 (D) 3>2>1>4 B
29. The correct order of basicity of the following compound H

is 35. Which compounds react with AgNO3 to give ppt

Br Br
Me3N Me 2NH MeNH2 NH3 (A) (B)

1 2 3 4

(A) 2>3>1>4 (B) 1>2>3>4 Br

(C) (D) none of the
(C) 4>3>2>1 (D) 3>2>4>1 above
30. The correct order of acidic strength of the following 36. The most basic compound among the following is
compound is
COOH COOH COOH

NO2 OMe NH2

1 2 3
(A) 1>2>3 (B) 3>2>1
(C) 1>3>2 (D) 2>1>3
31. The correct order of acidic strength of the following 37. Pka value of the given compound decreases if X is
compound is COOH
COOH COOH COOH
O2N

O2N O2N NO2

NO2 NO2 X
1 2 3 (A) -NH2 (B) -OMe
(A) 1>2>3 (B) 3>2>1 (C) –OH (D) -NO2
(C) 2>3>1 (D) 1>3>2 38. The correct order of basicity of the following compound
32. The correct order of acidic strength of the following is
compounds is O
COOH SO3H OH
N N N
H H
1 2 3
(A) 1>2>3 (B) 2>3>1
1 2 3 (C) 2>1>3 (D) 3>2>1
IFAS Publications
8 IIT JAM – Organic - Practice Book
39. The most basic compound among the following is 45. Correct order of Ka of the following acids is
COOH COOH COOH

OMe NO2

(1) (2) (3)

(A) 1>2>3 (B) 2>3>1
(C) 3>1>2 (D) 3>2>1
46. The correct acidity order of the following compound is
40. Compare carbon-carbon bond rotation around 1,2 and 3 OH OH COOH COOH

Cl

1 2 3 4
1 2 3
(A) 1>2>3 (B) 2>1>3 (A) 3>2>4>1 (B) 3>4>2>1
(C) 3>1>2 (D) 3>2>1 (C) 2>3>4>1 (D) 2>4>3>1
41. The most basic compound among the following is 47. Compound having dipole moment is

48. The correct order of acidity of the following compound is

42. Among the following the strongest acid is COOH
COOH COOH COOH
(A) C2H2 (B) C6H6 NO2
1) 2) 3) 4)
(C) CH3OH (D) CH3NH2 NO2
NO2
43. The correct order of acidity of the following compound is
OH
(A) 4>2>3>1 (B) 2>4>3>1
OH OH
NO2 (C) 4>3>2>1 (D) 1>2>3>4
49. The given compound is
NO2
NO2

(1) (2) (3)

(A) 1>2>3 (B) 2>3>1

(C) 2>1>3 (D) 3>2>1 (A) Aromatic
44. Compound having highest heat of hydrogenation is (B) Quasi aromatic
(C) Homo aromatic
(A) (B)
(D) Non aromatic
50. Which among the following compound is most aromatic?
(C) (D) (A) Pyrrole (B) Pyridine
(C) Thiophene (D) Furan

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Chapter – 2 GOC & Aromaticity 9
51. The decreasing order of basicity of the following 56. The correct order of acidic strength of the following
compound is compound is
(1) Phenol (2) p-Cresol
(3) m-Nitrophenol (4) p-Nitrophe
(A) 4>2>3>1 (B) 4>3>1>2
(C) 3>4>2>1 (D) 2>3>4>1
57. The increasing order of basicity of the following
compound is

(A) 3>2>1>4 (B) 3>1>2>4

(C) 3>4>2>1 (D) 4>3>2>1 (A) 1<2<3<4 (B) 2<1<4<3
52. The compound given below is (C) 3<4<1<2 (D) 3<1<4<2
58. Which of the following compound is most acidic?

(A) Aromatic (B) Antiaromatic

(C) Non aromatic (D) Quasi-aromatic
53. The strongest base among the following compounds is

59. Compound having highest resonance energy is

(A) Benzene
(B) Naphthalene
(C) Anthracene

54. The strongest base among the following compounds is (D) Phenanthrene
60. The resulting compound is

(A) Aromatic (B) Antiaromatic

(C) Homoaromatic (D) Non aromatic
61. The most aromatic compound among the following is
(A) Benzene
(B) Naphthalene
55. Arrange the following compound in decreasing order of
(C) Anthracene
basicity
(D) All are equally aromatic
62. The correct order of acidity of the following compound is

(A) 1>2>3>4 (B) 2>1>3>4 (A) 3>2>1 (B) 1>2>3

(C) 2>1>4>3 (D) 1>2>4>3 (C) 2>1>3 (D) 2>3>1

IFAS Publications
10 IIT JAM – Organic - Practice Book
63. Which of the following compound undergo fastest 69. The compound given below is
tautomerization?

(A) Aromatic (B) Antiaromatic

(C) Non-aromatic (D) Homoaromatic
70. The compound given below is

64. Which of the following compound will show cis trans

isomerism?

(A) Aromatic (B) Antiaromatic

(C) Non-aromatic (D) Homoaromatic
71. The compound given below is

65. Correct order of basic strength is

(A) Aromatic (B) Antiaromatic
(C) Non-aromatic (D) Homoaromatic
72. The compound given below is

(A) 1>2>3 (B) 2>3>1

(C) 3>2>1 (D) 3>1>2
66. The strongest acid among the following is
(A) FCH2COOH (B) ClCH2COOH
(A) Aromatic (B) Antiaromatic
(C) BrCH2COOH (D) ICH2COOH
(C) Non-aromatic (D) Homoaromatic
67. The strongest acid among the following is
73. The correct order of basicity of the following compound
is

(A) 1>2>3 (B) 2>3>1

68. The correct order of acidic strength of the following
(C) 3>2>1 (D) 3>1>2
compound is
74. The compound given below is

(A) 1>2>3 (B) 3>2>1 (A) Aromatic

(C) 2>1>3 (D) 3>1>2 (B) Antiaromatic
(C) Non-aromatic
(D) Homoaromatic

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Chapter – 2 GOC & Aromaticity 11
75. The compound given below is 3. Which of the following compound have permanent
N NH dipole moment?

(A) (B)

(A) Aromatic (B) Antiaromatic

(C) (D)
(C) Non-aromatic (D) None of the above
76. The compound given below is
4. Which of the following molecule in pure form unstable at
room temperature?

(A) Aromatic (B) Antiaromatic

(C) Non-aromatic (D) None of the above
77. Select the correct statement
H+

B O k1 5. Select the correct statement about azulene is

H
(A) Azulene is aromatic
H+
(B) Azulene has non-zero dipole moment
O O k2 (C) Azulene is non aromatic
(D) Azulene has zero dipole moment
+
H 6. Homoaromatic compound among the following is
O k3

(A) K1>K2>K3 (B) K2>K1>K3

(C) K2>K3>K1 (D) K3>K2>K1
78. The correct order of acidic strength of the following
compound is
CN
7. Which of the following compounds are aromatic?

1 2 3
(A) 1>2>3 (B) 2>3>1
(C) 3>1>2 (D) 3>2>1
MSQ
1. Which statement is true about resonance? 8. In which of the following compounds homoconjugation
(A) The hybridization of atoms does not change due to is possible
resonance
(B) Resonating structure cannot be isolated
(C) Resonance hybrid is more stable than any resonating
structure
(D) Resonance decreases the energy of the system
2. Which of the following compounds are aromatic?
9. Select the correct statement for compound given below
(A) (B) is
I
O2N NO2
b a
(C) (D)
c
NO2
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12 IIT JAM – Organic - Practice Book
(A) Bond length a = b 15. Among the following aromatic compounds are
(B) Bond length a>c Ph Ph
(C) Bond length b>c N N
(D) Bond length a not equal to b
10. Which of the following compounds are diamagnetic? (A) N (B)

Ph Ph
(C) (D)
N N
11. Which of the following compounds are paramagnetic? N
N

B
H
16. Which of the following compound have non-Zero dipole
moment?

12. Which of the following compounds are anti-aromatic?

(A) (B)

(C) (D) NAT

O 1. Identify total number of aromatic compounds
13. Aromatic compound among the following is

(A) (B) N O S
H
2. Identify total number of anti-aromatic compounds

(C) NH (D) 3. The total number of contributing structures showing

hyperconjugation for the following carbocation is
14. Aromatic compound among the following is

(A) (B) HN HN

4. The most basic nitrogen in the given compound is

1
NH2
(C) (D)

N2 N3
H

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Chapter – 2 GOC & Aromaticity 13
5. Which of the following acid react with NaHCO3 and 14. Number of π-bonds involve in the aromaticity is
liberate CO2?

15. Which nitrogen is most basic?

6. The most basic nitrogen in the given compound is

16. The most basic nitrogen in the compound given below is

7. Which of the following hydrogen is most acidic?

17. Identify total number of aromatic compounds

8. Which hydrogen atom deprotonated first

18. Total number of alpha hydrogens in the compound given

below is

9. Number of resonating structure of Anthracene is

10. Number of resonating structure of Phenanthrene is
11. Which of the following compound is stronger acid?

ANSWER KEY
MCQ
1 2 3 4 5 6 7 8 9 10
12. The compound given below follow huckel rule (4n+2) of
B C A D D A A D A D
aromaticity find value of n
11 12 13 14 15 16 17 18 19 20
B D C A A D B A C D
21 22 23 24 25 26 27 28 29 30
B C B D A B A A A A
31 32 33 34 35 36 37 38 39 40
A C C C B B D C C B
41 42 43 44 45 46 47 48 49 50
13. The compound given below follow huckel rule (4n+2) of
C C D A C B D B C B
aromaticity find value n 51 52 53 54 55 56 57 58 59 60
A C D C B B B B D A
61 62 63 64 65 66 67 68 69 70
A B A C C A D B C A
71. 72 73 74 75 76 77 78
C B C A A A C C
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14 IIT JAM – Organic - Practice Book
MSQ
1 2 3 4 5
8. (D)
A,B,C,D B,D B,D B,C A,B
9. (A) least stable due to positive charge near electron
6 7 8 9 10 withdrawing group.
A,B B,C,D A,C A,B,C A,B,C

11 12 13 14 15
A,B,D A,B,C C,D A,B,C A,B,C

16 10. (D)
A,B,C
NAT
1 2 3 4 5 6 7 8 9 10 1 is neutral most stable between 2 and 3. 3 is more stable
due to –ve charge present on most electronegative atom.
4 3 6 2 3 2 2 2 4 5
Stability order : 1 > 3 > 2
11 12 13 14 15 16 17 18
11. (B) From conjugate Acid-Base theory.
2 3 3 7 2 4 2 6
Strong Acid have weak conjugate base and vice-versa.

Solutions
1. (B) Inductive effect involving partial displacement of
sigma electrons.

2. (C) Inductive effect is polarization of sigma electrons.

3. (A) Delocalization of 𝜋-electrons. Another method:- left to right in Periodic table Basicity
decrease.

4. (D) All are correct.

12. (D)

13. (C)
5. (D) All Resonating structure not always have same
energy.
6. (A) Positive charge increase the electronegativity of that
atom. +N(Me3)3 stronger –I among all the four.
7. (A) 1 > 4 > 3 > 2. 3 is more stable than 2 due to –ve charge on
more electronegative elements.
14. (A)

𝜇 ⃗𝛼 = 𝜇 + 𝜇 + 2𝜇 𝜇 𝑐𝑜𝑠𝜃 𝜇 ⃗𝛼 1/ √𝜃
IFAS Publications
Chapter – 2 GOC & Aromaticity 15
15. (A) 24. (D) Number of hyperconjugation structure 𝛼 No of 𝛼-H

16. (D). All are aromatic. But aromatic hydrocarbon is:

25. (A)

17. (B)
26. (B) Heat of hyperconjugation 𝛼 1/ stability

Stability = 3 > 1 > 2, energy = 2 > 1 > 3

18. (A) Strong acid have weak conjugate base. Stability = 4 > 3 > 2 > 1
Acidity = HI > HBr > HCl > HF Heat of hyperconjugation = 1 > 2 > 3 > 4
Basicity = F- > Cl- > Br- > I- 27. (A)
O
19. (C) Hyperconjugation increase bond length of carbon-
carbon double bond. N N N N
H H H

sp3-N sp2-N sp3-N sp2-N

most basic (-I of O)

28. (A). Me3N > Me2NH > MeNH2 > NH3

20. (D) 29. (A). Me2NH > MeNH2 > Me3N > NH3

30. (A)

𝜇 ⃗𝛼 = 𝜇 + 𝜇 + 2𝜇 𝜇 𝑐𝑜𝑠𝜃 𝜇 ⃗𝛼 1/ √𝜃
21. (B)

31. (A)
22. (C)

Stability 𝛼 No of 𝛼-H
Between 3 and 1. 3 is more stable.
Stability = 2 > 4 > 3 > 1. Acidic Strength = 1 > 2 > 3
23. (B) Strong Acid have weak conjugate base and vice-versa.
Acidity = HCl > HF > CH3CCOOH > H2O
Basicity = HO- > AcO- > F- > Cl-

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16 IIT JAM – Organic - Practice Book
32. (C) 39. (C)

40. (B)

Acidic Strength = 2 > 1 > 3

33. (C)

41. (C)

34. (C)

35. (B)

42. (C) CH3OH → Most Acidic

CH3OH → CH3O + H+
−ve change on the most electromagnetic element
43. (D)
H-Bonding
36. (B) OH O OH OH
37. (D) lone Pka → high acidity N
O

NO2
-m, -I
NO2 -m
(1) -I
(2) (3)

Acidity = 3 > 1 > 2

44. (A) Heat of hydrogenation α , Stability α No of α -
If X is – NO2 it will ↑ the acidity i.e lowers the Pka.
38. (C) Hydrogens

High heat of hydrogenation

Basicity = 2 > 1 > 3

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Chapter – 2 GOC & Aromaticity 17
45. (C) 53. → (D)

54. → (C)

46. (B)

55. (B)

Acidity = 3 > 4 > 2 > 1

47. (D)

Basicity = 2 > 1 > 3 > 4

56. (B)

48. (B)

Basicity = 4 > 3 > 1 > 2

57. (B)
Acidity = 2 > 4 > 3 > 1
49. (C)

Basicity = 2 < 1 < 4 < 3

50. (B) Pyridine 58. (B)
51. (A)

59. (D) Number of Aromatic Ring ↑ Resonance energy ↑.

60. (A)

Basicity = 3 > 2 > 1 > 4

52. (C)
61. (A) Due to Annelation effect.

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18 IIT JAM – Organic - Practice Book
62. (B) 69. (C)

70. (A)

Acidity = 1 > 2 > 3 71. (C)

63. (A)

72. (B)

64. (C)

73. (C)

B, D are Aromatic No restricted rotation.

65. (C)

3>2>1
74. (A)

Basicity = 3 > 2 > 1

66. (A)
75. (A)

−I = −F > −Cl > −Br > −I

67. (D)
76. (A)

68. (B)
H H H 77. (C)
O O O S S S

(1) (2) (3)

O O O S S S
-I -I
-I -I -I Back bonding
Back bonding

Acidity = 3 > 2 > 1

K2 > K 3 > K 4
IFAS Publications
Chapter – 2 GOC & Aromaticity 19
78. (C) 10. (ABC) Aromatic compounds are diamagnetic. Anti
Aromatic compounds are Paramagnetic

11. (ABD) Aromatic compounds are diamagnetic, Anti

aromatic compounds are Paramagnetic
Acidity = 3 > 1 > 2
MSQ
1. (ABCD)
2. (BD)

12. (ABC)

3. (BD) same as above question

4. (BC)

13. (CD)

5. (AB) Azulene is Aromatic and has Non zero dipole

moment
6. (AB) 14. (ABC)

7. (BCD)

15. (ABC)
8. (AC)
9. (ABC)

a = b. Due to steric of Iodine ortho –NO2 group goes out

of plane and there is no conjugation with ring.
a=b>C

IFAS Publications
20 IIT JAM – Organic - Practice Book
16. (ABC) 101. (2)

102. (2)

All three have Non-Zero dipole moment

NAT 103. (4) Anthracene
95. (4)

96. (3)
104. (5) Phenanthrene

97. (6)

105. (2) Due to field effect more acidic

6α-H → Number of α-H = Number of Hyperconjugation

structure

98. (2) 106. (3)

14 π𝑒 follows Huckel rule 4n + 2

4n + 2 = 14
n=3
99. (3)
107. (3)

14 πe- → Aroma c follows Huckel rule 4n + 2

100. (2) 4n + 2 = 14
n=3
108. (3)

7 π bond involve in Aromaticity

from triple bond only one π – Bond is involved in
Aromaticity.
IFAS Publications
Chapter – 2 GOC & Aromaticity 21
109. (2) 4. Which among the following is the most deactivating
O sp3 localised most basic meta-directing group in aromatic substitution reaction?
(A) –COOH (B) -SO3H
N N
(C) -NO2 (D) -CN
5. Arrange the following on increasing order of basicity and
delocalised
give reason.
N
H delocalised

sp2
110. (4)
(A) Aniline >p-nitro aniline > o-methyl aniline
H2N O delocalised
delocalised HN (B) p-nitro aniline > o-methyl aniline >Aniline
(C) o-nitro aniline > Aniline > p-methyl aniline
Me2N (D) p-nitro aniline > Aniline > o-methyl aniline
N O
6. The correct order of decreasing acidity of nitrophenols
O O
will be:
(A) m-nitrophenols > p-nitrophenols > o-nitrophenols
localised lone pair
most basic
(B) o-nitrophenols > m-nitrophenols > p-nitrophenols
(C) p-nitrophenols > m-nitrophenols > o-nitrophenols
111. (2)
(D) p-nitrophenols > o-nitrophenols > m-nitrophenols
H
B 7. Arrange in order of increasing acidic strength
, Aromatic H3N NH3
112. (6)
Z Y
H COOH
H X
H
(A) X > Z > Y (B) Z < X > Y
6 -H
(C) X > Y > Z (D) Z > X > Y
H 8. In the following carbocation; H/CH3 that is most likely to
H
H migrate to the positively charged carbon is
PART-2 H H

1. Nucleophilicity order is correctly represented by: H3C C C C CH3

1 2 3
(A) CH3- < NH2- < HO- < F-
OH H CH3
(B) CH3- = NH2- < HO- = F-
(A) CH3 at C-3 (B) H at C-1
(C) CH3- > NH2- > HO- > F-
(C) CH3 at C-1 (D) H at C-3
(D) NH2- > F- > HO- > CH3-
9. Increasing order of pKa values (pKa = - log Ka) of H2O,
2. The correct decreasing order of -I effect is
CH3OH and C6H5OH is:
(A) -F > -COOH > -NO2 > -CN
(A) H2O < CH3OH < C6H5OH
(B) -CN > -NO2 > -COOH > -F
(B) CH3OH < H2O < C6H5OH
(C) -NO2 > -CN > -COOH > -F
(C) C6H5OH < H2O < CH3OH
(D) -NO2 > -F > -COOH > -CN
(D) C6H5OH < CH3OH < H2O
3. Which effect presents in the following molecule
10. Identify the correct order of boiling points of the
H
N following compounds
1. Butan-1-ol 2. Butyraldehyde 3. Butyric acid
O
(A) 1 > 2 > 3 (B) 3 > 1 > 2
(A) +Mesomeric (B) - Mesomeric (C) 3 > 1 > 2 (D) 3 > 2 > 1
(C) -Inductive (D) +Inductive
11. Which of the following, has the most acidic hydrogen?
IFAS Publications
22 IIT JAM – Organic - Practice Book
(A) 3-hexanone (A) CH3OH > CH3CH2OH > (CH3)2CHOH
(B) 2, 4-hexanedione (B) CH3OH > (CH3)2CHOH > CH3CH2OH
(C) 2, 5-hexanedione (C) CH3CH2OH > (CH3)2CHOH > CH3OH
(D) 2,3-hexanedione (D) (CH3)2CHOH > CH3CH2OH > CH3OH
12. Among the following, the molecule with the highest 20. What is the order of acidity of H2O, ROH, RNH2, C2H2?
dipole moment is (A) C2H2 > H2O > ROH > RNH2
(A) CH3Cl (B) CH2Cl2 (B) RNH2 > C2H2 > H2O > ROH
(C) CH2Cl2 (D) CCl4 (C) ROH > RNH2 > C2H2 > H2O
13. Among the following compounds, the most acidic is (D) H2O > ROH > RNH2 > C2H2
(A) p-nitrophenol 21. Which of the following is the most stabilized
(B) p-hydroxybenzoic acid carbocation?
(C) o-hydroxybenzoic acid
(D) p-toluic acid
14. The configuration of C-2 and C-3 atoms in compound A
are:

22. The most stable carbocation is:

(A) RR (B) SS
(C) RS (D) SR
15. Which of the following compound is aromatic Alcohol?
OH CH2OH
23. The most stable resonating structure for the following

A) B)

OH
OCH3

C) D)

CH3
CH3

16. Which is weakest acid in the following? 24. The correct order of alkene towards reactivity of
(A) CH3OH (B) (CH3)2CHOH electrophile
(C) CH3CH2OH (D) (CH3)3COH
17. Which of the following has highest boiling point?
(A) Methanol (B) Ethanol
(C) Propan-1-ol (D) Butan-1-ol
18. Arrange the following alcohols in order of increasing
reactivity towards sodium metal. (A) III> II > I > IV
(i) (CH3)3C-OH (B) III > IV > I > II
(ii) (CH3)2CH-OH (C) III> I> II> IV
(iii) CH3CH2OH (D) IV > III > II > I
(a) (iii) < (ii) < (i) (b) (ii) > (i) < (iii)
(c) (i) < (ii) < (iii) (d) (iii) < (i) < (ii)
19. In the esterification reaction, the correct order of
reactivity of alcohols is:

IFAS Publications
Chapter – 2 GOC & Aromaticity 23
25. The correct order of the reactivity of alkene towards 33. The most electron rich alkene is
electrophile

34. The optically inactive compound from the following is

(A) 2-chloropropanal
(B) 2-chloropentane
(C) 2-chlorobutane
(A) S>R>P>Q (B) S>P>R>Q (D) 2-chloro-2-methylbutane
(C) R>S>Q>P (D) S>R>Q>P 35. What is DDT (Dichloro diphenyl trichloroethane) among
26. The correct order reactivity of benzene ring towards the following?
electrophile (A) A fertilizer
(B) Biodegradable pollutant
(C) Non-biodegradable pollutant
(D) Greenhouse gas
36. Which of the following will have a meso-isomer also?
(A) Q>R>S >P (B) Q>R>P>S (A) 2-chlorobutane
(C) P>Q>R>S (D) S>Q>P>R (B) 2,3-dichlorobutane
27. The most reactive benzene ring towards electrophile (C) 2,3-dichloropentane
(D) 2-hydroxypropanoic acid
ANSWER KEY
1 2 3 4 5 6 7 8 9 10
28. The correct order of the stability of carbocation is C C C C C D A B C B
11 12 13 14 15 16 17 18 19 20
B A C A B A D C A D
21 22 23 24 25 26 27 28 29 30
3 1 2 C D A 3 D 4 4
(A) P>R>Q>S (B) S>R>Q>P 31 32 33 34 35 36
(C) S>P>R>Q (D) S>R>P>Q 4 3 3 D C B
29. The most reactive benzene ring towards electrophile
Solutions
1. Sol. As electronegativity of the central atom decreases,
its nucleophilicity increases. Here, carbon has the
least electronegativity. So, CH3− will have the
30. The most stable carbanion is
highest nucleophilicity.
So, the correct order is F− < OH − < NH2 − < CH3−
2. Sol. As electronegativity of the central atom increases, its
31. The most stable carbanion is -I effect increases.
As electronegativity of surrounding atom increases -I
effect increases.
Here, F is more electronegative but NO2 surrounding
32. Which has least heat of hydrogenation - atom O is more electronegative. So, NO2 will have the
highest -I effect.
So, the correct order is c. -NO2 > -CN > -COOH > -F

IFAS Publications
24
3. Sol. Here, N lone pair is in conjugation with benzene ring, N
lone pair donates its electron to the benzene ring therefore,
molecule having + Mesomeric effect.
So, the correct option is (a) +Mesomeric
4. Sol. Here, most deactivating group is -NO2 because it has
strong -I effect.
So, the correct option is (c) -NO2
5. Sol. Aniline is a Lewis base due to presence of lone pair
of electrons on nitrogen atom. An electron releasing
group having + I effect such as – CH3 increases the
electron density on the N – atom and basicity increases.
On the other hand, an electron withdrawing group
having – I effect such as – NO2 decreases the electron
density on the N – atom and basicity decreases. Hence
the order of basicity is:
So, the correct option is c) o-nitro aniline > Aniline > p-methyl
aniline
6. Sol. The presence of electron withdrawing groups in the
aromatic ring increases their acidity, In the case of nitro
substituents, the inductive effect would be expected to
fall off with distance on going from ortho to meta and
finally to para-nitrophenol but there would also be an
electron-withdrawing mesomeric effect when the nitro
group is in the ortho- and para position, but not in the
meta- position and this too would promote ionisation by
stabilisation of the resultant anion.
So, the correct option is d) p-nitrophenols > o-nitrophenols >
m-nitrophenols
7. Sol. Here, X is COOH after dissociation of COOH, we get
H+ readily and Z is NH3+ is adjacent to COOH therefore z
is more acidic than Y (NH3+).
So, the correct option is (a) X > Z > Y
8. Sol.
Hydride
shift from
H H H H
C-1 to C-2
H3C C C C CH3 H3C C C
1 2 3 1
OH H CH3 OH
driving force is
conjugation from oxygen
The positive charge on C-2 is hyperconjugation stabilized
due to the neighbouring oxygen.
So, the correct option is (b) H at C-1
IFAS Publications
IIT JAM – Organic - Practice Book
9. Sol. pKa value of Phenol: 10.0
pKa value of Water :14.0
pKa value of Methanol: 15.54
So, the correct option is (c) C6H5OH < H2O < CH3OH
10. Sol. Carboxylic acids rare more acidic than alcohols.
Carboxylic acids react with Na, NaOH, Na 2CO3 and
NaHCO3. But alcohols only react with Na. Reason
is, carboxylate anion is more stable than alkoxide anion.
The anion forming, when H is removed from carboxylic
acid is called as carboxylate anion.
Carboxylate anion can show resonance structures.
Therefore, carboxylate anion can spread it's negative
charge by carbonyl group. So that brings a stability to the
carboxylate anion and equilibrium goes to the right side
So, the correct option is (b) 3 > 1 > 2
11. Sol. 2,4 Hexanedione has most acidic hydrogen this is
because the Carbanion left after the removal of H + is
resonance.
So, the correct option is (b) 2, 4-hexanedione
12. Sol. Dipole moments tell us about the charge separation
in a molecule. The larger the difference in
electronegativities of bonded atoms, the larger the
dipole moment.
For example, CH3Cl has the highest dipole moment
because it has an ionic bond (i.e. highest charge
separation).
So, the correct option is (a) CH3Cl
13. Sol. o-hydroxy benzoic acid is most acidic because after
loss of H+ the COO- is stabilised by H-Bonding with OH
group.
C CH3
2 3
H CH 3
So, the correct option is (c) o-hydroxybenzoic acid
14. Sol. At second carbon, H is above, so the 2S configuration
change to 2R.
At third carbon, H above, so the 3S configuration change
to 3R.
Chapter – 2 GOC & Aromaticity 25
2 20. Sol. The conjugate bases are as follows −OH, RO-, RNH-
3
, −C2H2.
1 COOH 1 COOH
4 2R Between stability of −OH and RO-, The RO− is unstable.
H NH2 1
2
H NH2
2
1 H2N 4 Also, in RNH-, the negative charge is on nitrogen atom
H2N 3 H 3 H
4 COOH
3R 4 COOH making it more unstable than the other two groups.
3 2
compound A compound A In −C2H the pi electron cloud will face repulsion of with
the negative charge on the carbon atom.
So, by this logic, decreasing order of acidity should be:
So, the correct option is (a) RR
H2O > ROH > RNH2 > C2H2
15. Sol.
Here in option A and C hydroxy group directly attached
to benzene ring, So A and D is phenol, In option D, methyl
group and phenyl group is attached to Oxygen, therefore,
it is ether. In option B hydroxy group is attached to sp3
hybridised carbon. Hence, it is a alcohol, So correct
option is B. So, the correct option is d. H2O > ROH > RNH2 > C2H2
So, the correct option is ANS:B 21. Sol. 3 is most stable due to the presence of resonance on
16. Sol. The correct increasing order of acidity is: both sides with double bonds. Also, it is 3o carbocation and
(CH3)3C−OH<(CH3)2CH−OH<CH3−OH shows hyperconjugation.
For an acid to be strong its conjugate base anion has to be So, the correct option is ANS:3
very stable. Only then acid will disassociate faster to give 22. Sol. 1 is most stable due to lone pair of Nitrogen is in conjugation with
hydronium ion. double bond. So, the first carbocation is most stable.
As we can see in the figure, conjugate base 1 has a negatively So, the correct option is ANS:1
charged O atom and 3 CH3 +I groups attached to it. So, it is 23. Sol. The most stable resonating structure is 2. because, lone pair of N i
least stable. Again, 3 has no +I groups, so it is most stable, in conjugation with double bond, lone pair of nitrogen is more basi
and hence the most acidic. therefore, correct option is 2.
CH3 CH3 So, the correct option is ANS:2
CH3-O- 24. Sol. As the basicity increases nucleophilicity is increases, in
H 3C O- H 3C O- 3 option 3 lone pair of nitrogen is more basic than oxygen, So,
CH3 H
option 3 comes first then 1 then 2 because in option 2 L.P of
1 2 oxygen involved in conjugation with 2 double bonds so the
So, the correct option is (a) CH3OH reactivity towards the electrophile is decreases then option
17. Sol. As the molecular weight increases Boiling point is 4 because it does not have L.P, So, it is less nucleophilic.
increases. Hence, more energy required to break So, the correct option is (c) III> I> II> IV
intermolecular forces, So the B.P of Butan-1-ol is higher. 25. Sol. Basicity order- Alcohol>Ether>Ester
So, the correct option is (d) Butan-1-ol Basicity is directly proportional to the nucleophilicity.
18. Sol. More the number of methyl groups (electrons releasing) Alcohol is more basic/nucleophilic than ether. So,
lesser will be the acidity. Hence the reactivity towards reactivity of alkene toward the electrophile is more for S.
sodium metal will be tert < sec < prim. So, the correct option is (d) S>R>Q>P
So, the correct option is(c) (i) < (ii) < (iii) 26. Sol. As the nucleophilicity is increases reactivity towards the
19. Sol. In the esterification reaction, the alcohol acts as a electrophile is increases.
nucleophile (RO−). The nucleophilicity order is: CH3O− > CH3 Option Q compound is more reactive towards electrophile
CH2O− > (CH3)2CHO− As the bulkiness of the nucleophilic because the L.P of Nitrogen is more basic.
group increases the reactivity towards esterification So, the correct option is ANS-(a)
decreases 27. Sol. Basicity is directly proportional to the nucleophilicity.
So, the correct option is a. CH3OH > CH3CH2OH > As the nucleophilicity is increases reactivity towards the
(CH3)2CHOH electrophile is increases.

IFAS Publications
26 IIT JAM – Organic - Practice Book
Option 3 compound is more reactive towards electrophile
because the L.P of Nitrogen is more basic.
So, the correct option is ANS-3
28. Sol. Carbocation is stabilised by the electron-donating group
at the adjacent position. In option S nitrogen adjacent to
carbocation, nitrogen L.P stabilises carbocation.
So, the correct option is (d) S>R>P>Q
29. Sol. As the nucleophilicity is increases reactivity towards the So, the correct option is (b) 2,3-dichlorobutane
electrophile is increases. Option 4 compound functional
group is ring activating , So the 4 is more reactive towards
electrophile.
So, the correct option is ANS-4
30. Sol. Carbanion is stabilised by the electron-withdrawing
group at the adjacent position. S have vacant d orbital.
So, the correct option is ANS-4
31. Sol. Carbanion is stabilised by the electron-withdrawing
group at the adjacent position. P have vacant d orbital.
So, the correct option is ANS-4
32. Sol. As the number of substituents on double bond is
increases heat of hydrogenation is decreases.
So, the correct option is ANS-3
33. Sol. Option 3 alkene is most electron rich. because L.P of
nitrogen is in conjugation with double bond. option 2 alkene
adjacent nitrogen L.P is involved in conjugation with phenyl
ring so the nucleophilicity is decreases in 2.
So, the correct option is ANS-3
34. Sol. 2-chloro-2-methylbutane is optically inactive as no chiral
centre is present.

So, the correct option is (d) 2-chloro-2-methylbutane

35. Sol. The expanded form of DDT is
Dichlorodiphenyltrichloroethane. It is a colourless,
tasteless, and almost odourless crystalline
organochlorine chemical compound. Its chemical
formula is C14H9Cl5. It is Non-biodegradable pollutant
So, the correct option is (c) Non-biodegradable pollutant
36. Sol. 2,3-dichlorobutane has 2 identical chiral centre and
plane of symmetry. Hence it is a meso isomer.

IFAS Publications
 CHAPTER
STEREOCHEMISTRY
MCQ
1. Stereoisomers has different 6. Which of the following has center of symmetry?
(A) Structural formula
(B) Molecular mass
(C) Configuration
(D) Molecular formula
2. Which of the following can show cis trans isomerism?

7. Stereoisomers which are not mirror image of each other

called
(A) Enantiomers (B) Meso
3. What is the necessary condition for a molecule to be (C) Diastereomers (D) Tautomer’s
chiral 8. The instrument which can be used to measure optical
(A) Absence of axis of symmetry activity
(B) Absence of plane of symmetry (A) Photometer (B) Polarimeter
(C) Absence of improper axis of symmetry (C) Voltmeter (D) Refractometer
(D) Absence of center of symmetry 9. The Baeyer’s strain is maximum in
4. Number of chiral centers in the given compound is (A) Cyclopropane (B) Cyclobutene
(C) Cyclopentane (D) Cyclohexane
10. The least stable conformation of cyclohexane is
(A) Chair (B) Boat
(C) Twist boat (D) Half chair
11. Flagpole interaction is present in
(A) Chair (B) Boat
(C) Twist boat (D) Half chair
(A) 19 (B) 20 12. Isomers which can be interconverted through rotation
(C) 21 (D) 22 around single bond is called
5. Number of chiral center in the given compound is (A) Enantiomers (B) Diastereomers
HO O (C) Conformers (D) Positional isomers
13. Which of the following has highest potential energy for
O pentane?
O
(A) Anti-conformation
O (B) Gauche conformation
(C) Eclipsed conformation
(D) All have same energy
14. The absolute configuration of the given compound is
(A) 7 (B) 8 COOH
HOOC
(C) 9 (D) 10 HO H
(A) R (B) S
(C) r (D) s