Solution Manual to Master Problems in Organic Chemistry 2021 by Vineet Khatri

, SOLUTIONS TO
MASTER PROBLEMS IN
ORGANIC CHEMISTRY
[1 EDITION]
ST




VINEET KHATRI, IIT ROORKEE

FOUNDER OF ATP STAR, KOTA

353, Rajeev Gandhi Nagar, Instrumentation Limited
Colony, Kota, Rajasthan-324005

, 1 IUPAC NOMENCLATURE



1. (a)
2° 2°
H H

O
Sol. 2° H atoms are indicated
H
2°



2. (d)
O
O C
Sol. OMe
C N
DBE = Number of  bonds + Number of rings
=4+3=7

3. (b)
Acyl
halide Alcohol
O OH Ester
O O
Cl
Sol. O
Alkene
O Ether
Aldehyde

4. (d)
OH
Sol. CH2=CH–CH2–CH2–C–Me
CH2–Me

5. (b)
OH O
Sol. 3 1
6 5 4 2 OH

6. (b)
OH
C
Sol. CH3 CH3
(Tertiary alcohol)
CH3

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,7. (c)
Sol. The two methyl groups at the left are branched while the O atom at the right is of ketone group (from the
zero H atoms present on C atom present at left of oxygen atom.)

8. (b)
Sol. N atom of 2° amine is directly attached with two other C atoms.

9. (d)
Sol. 1° H-atoms are shown
O
H

H H
H H
H
O H
H

10. (b)
O
C
H
Sol.

C
O OH

11. (c)
Sol. Only C has DBE = 4, same as benzene.

12. (b)
5
6 Br
4
3
Sol. Cl
1
2
F

13. (d)
Sol. 1° prefix indicates cyclic or acyclic nature of parent chain.

14. (a)

F Locant
Sol. 5
3
2 4
1
15. (b)
OEt

Sol. 3 1 Correct name is 3-ethoxybut-1-ene
4 2




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,16. (c)
2°
NH 2° 2°
Sol.
2° 2°
2° OH

17. (d)
OH
1
3
4 2
Sol. 5
6

F

18. (b)
CN
OH
Sol.
O


19. (a)




Sol.



20. (a)

Sol.

 bonds = 26
 bonds = 7
21. (c)
Sol. Three  bonds contain a total of 6e–
22. (c)
Sol. 2° H atoms are indicated below.
H
H
H
O

H

23. (d)
Sol. In (a), (b) and (c) functional group is changed.




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,24. (b)
ether
O O acid
O anhydride
ket O
Sol. one
O

O aldehyde


25. (c)
6 4 2
7 5 3 1
Sol.
OH
Correct name is hept-5-en-3-ol
26. (c)
Sol. Alcohol has higher priority than thiol.
27. (a)
6
5 1
Sol. 4 2
3


5-ethyl-1-methyl cyclohexene

28. (b)
Ester
O
O 2° amide
O NH
Acid anhydride
Sol. O O

SH Ether O O
Thio alcohol

29. (c)
9 7 5
8 6
4
Sol. 3 1
2

30. (c)
2
3 1 OH
Sol. 4  6-amino cyclohex-3-enol
6 NH2
5




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,31. (a)
3 1
Sol. 4
1-chlorobut-2-ene
2 Cl

32. (d)
2 1
3 5
Sol. 4
6 Number of ‘C’ in parent chain are 6

Name : 3, 4-dimethylhexane.

33. (c)

Sol. No. of  Bond No. of Rings DBE (c) has odd no. of DBE value.
(A) 3 1 4
(B) 7 3 10
(C) 8 1 9
(D) 2 2 4


34. (c)
OH
OH

Sol. (a) (b)
2º alcohol 2º alcohol

OH F


(c) (d)
OH
3º alcohol 2º alcohol


35. (d)
R .. R
N
Sol. 3° amine
R

36. (c)
4
3 5
Sol. 2 1 Give lowest possible number to maximum substituents.
Cl
Br Cl




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,37. (b)
Cl
6
5 1
Sol.
2
Br 4
3




Rule :
(a) (-Bond > Branch)
(b) Give lowest possible number to maximum substituents.
IUPAC Name : 4-bromo-6-chloro-3-cyclobutylcyclohexene



38. (c)


10
9
Sol. 6 2, 5, 8-trimethyl-4-(2-methylpropyl)decane
1 2 4 5 8
3 7

39. (a)
H 3C CH3
CH – C C–C CH 3
Sol. H 3C 5 4 3 2 CH3
6 1

40. (d)
4
1
3 OH
2

2 1 6
3
5
Sol. Cl
4 Prefix Name : 3-chloro-4-cyclopropylcyclohexa-1,3-dienyl



IUPAC name : 2-(3-chloro-4-cyclopropylcyclohexa-1,3-dienyl)cyclobutanol

41. (c)
5
6 C2H5
4
Sol. IUPAC name : 6-ethyl-1-methylcyclohexene
3
1 CH3
2

42. (c)
1 2 3 4 5 6 7
Sol. CH3 – CH = CH – CH = CH – CH2CH3 IUPAC name : Hepta-2,4-diene


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,43. (b)


Sol.
C5H10 C6H12
In the other options, the functional group is different.

44. (c)
O
O O
Sol. (a) (b) (c) (d) O
C3H6O C3H6O
C3H6O C3H4O

45. (c)
1º CH – OH
Sol. 2


1º CH – OH
2

Glycol


46. (d)
Cl 10 2
1 3
9
Sol. 4 IUPAC name : 8-Bromo-9-chlorocyclodeca-1,5-diene
8 6
Br 7 5

47. (b)
O
Sol. 3 2 1 IUPAC name : 3-methyl-2-methylidenebut-3-en-1-oic acid
4 OH

48. (b)
Phenyl
O
3 2
Sol. CH=CH–C–OH IUPAC name : 3-phenylprop-2-enoic acid
1




49. (c)
1 2 3 4
Sol. CH3 – CH – CH2 – CH2 – O – CH2 – CH3 IUPAC name : 4-ethoxybutan-2-ol
OH Ethoxy

50. (b)
2 3

4 Br
Sol. 1
IUPAC name : 4, 4-dibromo-1-chlorocyclobutene
Cl Br

51. (b)
6 5 4 3 2 1
Sol. HC C – CH2 – CH – CH = CH 2 IUPAC name : 3-Bromohex-1-en-5-yne
Br



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, 52. (c)
O

O
Sol. 4-Ethanoyloxypentanoic acid 4 2 O
5 3 1
OH

53. (c)
Cl Br
2 4 3
1 1
Sol. (a) 3 (b) Cl 2
Br 1-Bromo-1-chloro propane
1-Bromo-2-chlorobutane
3 1
3 1 2
2 4
4 Cl
(c) Cl (d) Br
Br
Br
2, 2-Dibromo-1-chloro butane
2-Bromo-1-chloro butane
54. (d)
Br
2 1
Sol. COOH 2-bromo-2-phenylethanoic acid

2
1 3-cyclobutylpropanoic acid
HOOC 3



55. (a)
H
H H

Sol. H H 12, 3
H
CH2 = CH2 5, 1
CH3 – C  C – H 6, 2
H H
H H

H 19, 5
H
H H

56. (c)

4
3 5
N OH
Sol. O 6  3-Cyano-2-ethyl-5-(1-hydroxyethyl)hex-5-enamide
2
1

NH2



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