1. What could be the reagent for the following reaction?

O H3CH2CO OCH2CH3
Reagent cat. acid
CH3 Removal of H2O CH3

(a) CH3COCH3 (b) CH3OH (c) CH3CH2OH (d) HOCH2CH2OH

2. What could be the product for the following reaction?

CH3
(i) Mg, Et2O
Br
(ii) CD2O
Product?
(iii) H2O
D OH
CH2OD CH3 CH3 D
(a) (b) (c) (d) CH3
CH3 H D

3. What could be the major product for the following reaction?

O
(i) EtMgBr (1 equivalent)
OH Product?
(ii) HCl, H2O

HO HO O O
(a) (b) (c) (d)
OH

4. What could be the product for the following reaction?

O
(i) NaBH4
Product?
H (ii) H+, H2O
OH OH
OH O
(a) (b) (c) (d)
H
OH
H
5. What could be the product for the following reaction?
O
(i) CH3MgBr
Product?
(ii) H+, H2O
8.30 chapter eight

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

6. What is not the name for the following compound?

CH3
C
H3C O

(a) 2-Acetaldehyde (b) propanone (c) acetone (d) dimethyl ketone

7. What could be the reagent for the following reaction?

O Reagent NCH2CH3

(a) H2N–Ph, removal of water

(b) H2NCH2CH3, CH3CO2H, removal of water
(c) H2NCH3, H2O, removal of water
(d) H2NCH2CH2CH3, CH3CO2H, removal of water

8. What could be the reagent for the following reaction?

O O O
Reagent cat. acid
Removal of H2O

(a) CH3COCH3 (b) HOCH2CH2OH (c) CH3CH2OH (d) CH3OH

OH
OH
9. Dil. H2SO4
Major product is?
O OH
OH
OH OH
OH OH
OH
(a) (b) (c) (d)
O O OH
O OH H O OH

10. Conc. H2SO4

Major product is?

OH
OH
 organic reaction mechanisms and reagents 8.31

(a) (b)

O OH
O

(c) (d)

OH
O

OH
11.
Conc. H2SO4
Major product is?
∆

OH O
(a) (b) HO (c) (d)

OH
12. Conc. H2SO4
Major product is?
∆

(a) (b)

O
(c) (d)

13. Dil. H2SO4

Major product is?
HO OH
OH HO
(a) (b)

HO OH HO OH
8.32 chapter eight

(c) (d)
H H
O O
O O

14. Conc. H2SO4

Major prodcut is?
∆

O OH
(a) (b) (c) (d)

OH
15. 1 equivalent mCPBA
Major product is?

OH OH
O O
(a) (b)

OH O OH O
(c) (d)

16. (i) O3
Major product is?
(ii) PPh3
OEt
O O O O
H H OH H
H H H
H
(a) O (b) O
O O
O O
OEt OEt

O O
H
Et O H
(c) H (d) None of these
O
H
O
O
 organic reaction mechanisms and reagents 8.33

Me O

17. (i) BH3 - THF

O Major product is?
(ii) H2O2

Me O Me O Me O Me OH
OH
(a) O (b) O (c) O (d) O

H OH
H OH H OH OH

H
(i) mCPBA
(ii) DIBAL-H
18. Major product is?
(iii) H3O+
Me

H H

(a) (b)
Me H
HO Me
Me
H Me OH
H H

(c) (d)
Me Me
Me
OH OH Me

O
Cl
19. (i) Excess of Me MgCl
Major product
(ii) H2O / H+
HO

OH OH

(a) (b)

HO HO

OH
(c) (d)

HO OH
8.34 chapter eight

(i) O3 / H2O2
20. (ii) Excess of MeOH /H+
Major product is?
(iii) NaOMe / MeOH

O O O
(a) (b)
OMe

O O O
O O
(c) OMe (d)
MeO OMe

(i) MeOH / H+
O
(ii) NaOMe / MeOH
21. Major product of reaction is?
OH (iii) Aqueous NaOH
(iv) H+ /∆

O
O
O O
(a)   (b) (c) (d)
OMe
O

(i) SH SH / H+
22. O (ii) 2 eq. RLi/Cl Cl
H C H Major product is?
(iii) H3O+

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

(i) SOCl2
(ii) NaN3
O
(iii) Ag2O /∆
Major product is?
OH
23. (iv) H2O
O
(v) OH
N
(vi) LAH
 organic reaction mechanisms and reagents 8.35

H
(a) (b)
N
N
H

(c) N O (d) NH2

(i) NaCN
(ii) NH3 /∆ / H+
24.
Ph O (iii) HCN
Major product is?
(iv) H3O+

HOOC COOH HOOC COOH

(a) (b)
Ph Ph NH2

COOH COOH
(c) (d)
Ph NH2 Ph

(i) PBr3 (2 eq.)

25. CH2OH (ii) O O
OEt NaOEt
MeO H
Major product is?
H OMe (iii) Aq. NaOH
(iv) H+ /∆
CH2OH

O
MeO MeO
(a) (b) O

MeO MeO

O O

MeO MeO
(c) (d)

MeO MeO

O
(i) HCN
26. (ii) LiAlH4
Major product is?
(iii) NaNO2 + HCl
8.36 chapter eight

OH
O
(a) (b)

O
NH2
(c) (d)

Me

27. (i) 1% HgSO4 / dil H2SO4

Major product is?
(ii) OH /∆
O

(a) (b)
O

(c) (d)
O

O (i) KOH Br
(ii) O3 / Me2S
28. Major product is?
NH
(iii) KCN, NH4Cl
(iv) H3O+ /∆
O

COOH COOH
H2N
(a) (b)
NH2 NH2
COOH
(c) COOH (d)
H2N
NH2

(i) BuLi
S
(ii) 5 equivalent Br Br
29. Major product is?
S (iii) Dil. H2SO4
(iv) OH /∆

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

Et
 organic reaction mechanisms and reagents 8.37

O O (i) H⊕
OH OH
30. (ii) BuLi (excess)
OH
Major product is?
(iii) Dil. H2SO4
(iv) OH /∆

(a) (b)
O
O

O
(c) (d)

(i) CH CNa⊕
31. (ii) HgSO4, dil H2SO4
O Major product is?
(iii) Ph–CHO / OH

O O
(a) Ph (b)
Ph

O
Ph
(c) (d)
Ph
OH

(i) AC2O
(ii) HNO3, H2SO4
NH2 (iii) H3O+
(iv) Br2 + NaHCO3
32. Major product of reaction?
(v) NaNO2 + HCl
(vi) H3PO2
(vii) Fe + HCl
(viii) OH / H2O

NO2 NO2 NH2 COOH

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

Br Br Br Br Br Br Br
8.38 chapter eight

(i) 2 equivalent NaOEt

O O (ii) Br
33. Br
Major product is?
EtO OEt (iii) H3O+/∆

O
(a) COOH (b)
C OEt

O O COOH
(c) HO OH (d)

CH3
(i) Br2 / Fe
(ii) K2Cr2O7 / H+ / ∆
34. Identify product?
(iii) Li / Et2O
(iv) CO2 / H+

CH3 O OH OH
O

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

HO O Br
HO O

CH3 (i) HNO3 / H2SO4 /∆

(ii) LAH
(iii) NaNO2 + HCl / 0–5°C
35. Identify product?
(iv) CuCN

CH3 COOH NO2

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

CN CN CN

Cl
(i) HNO3 / H2SO4 /∆
(ii) CH3Cl / AlCl3
36. Identify product?
(iii) Sn /HCl
(iv) NaOH /H2O
 organic reaction mechanisms and reagents 8.39

Cl Cl Cl Cl
CH3 COOH

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

NH2 NH2 NH2 NO2

Cl (i) Li / Et2O
(ii) HCHO Then H+
(iii) HCl
37. Identify product?
(iv) Li / Et2O
(v) CO2, Then H+

Cl COOH COOH
COOH

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

HO O Cl COOH

CONH2

NaOH / Br2
38. Identify product?

MeO

OMe

COOH NH2 NH2

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

MeO
MeO MeO
OMe
OMe OMe OMe

39. In the presence of a base, the compound below cyclizes to give a compound Y.
O
H3C CH3
Na2CO3
H2O
O
Identify the structure of compound Y.
8.40 chapter eight

CH3 CH3 CH3

O CH3
(a) (b) O (c) O (d)
HO
OH OH HO O

(i) CH3COCl / AlCl3

40. (ii) Zn–Hg /HCl Identify product?
(iii) Br2 / hν

Br Br
Br

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

H3C Br
H3C O H3C

O OH O O

HO H3C O CH3
41. Identify product?

O OH O O O

(a) O O (b) HO

O OH

HO
(c) (d)
O

CH3

O O

Br
42. N Product. Identify product?
+
OH

O
 organic reaction mechanisms and reagents 8.41

O
O O
O
(a) (b)

Br
O O

(c) O (d) O
O

O BF3 / MeCN
43. H3C H Identify product?
H CONH2

N N
H3C CH3 CH3
(a) (b)
O O
H2NOC H2NOC
N
CH3 H3C CH3
O
(c) H3C (d)
SPh H3C O
H3C O H2NOC

HOOC COOH
(i) NaOH, H2O
44. Identify product?
O O (ii) H3O+

HOOC OH HOOC OH
(a) (b)

CH3 COOH COOH COOH

OHC OH
(c) (d)

COOH CHO

OH

O
H3C O PhSNa, H2O
45. Identify product?
H3C O
8.42 chapter eight

CH3
O O OH
H3C H3C
SPh SPh
(a) (b)
H3C O H3C O
CH3 OH

CH3 CH3
O O
(c) H3C (d) H3C
SPh SPh
H3C O H3C O

O OH
Excess of NaOH,
H2O
46. Identify product?
Excess of HCHO
O O

H3C CH3

OH OH
OH OH

H3C CH3
(a) (b)
O O O O
HO
H3C CH3 OH
OH OH
OH OH

(c) (d)
O O O O OH

H3C CH3 H3C CH3

O
O (i) NaOH, H2O
47. Identify product?
(ii) H3O+
CH3
CH3
CH3 CH3
H3C H3C
(a) HOOC COOH (b) O
COOH

CH3
H3C COOH
O COOH H3C
(c) (d) O CH3

COOH
 organic reaction mechanisms and reagents 8.43

N OTs + 2eq. BuLi

48. Identify product?

O
O

(a) N (b)

O
N O
H

O
O
(c) (d)

N O
H
N O
H

Br Br
BuLi
49. Identify product?

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

Br Br
2 eq. of NaI
Acetone /∆
50. Identify product?

Br Br

(a) (b)
8.44 chapter eight

(c) (d)

H2N NaNO2, then HCl

0 °C
51. Identify product?
then, ∆
NH

(a) (b)

(c) (d)
N N
H
COOH
H2N NH2

H3O+
52. Identify product?
∆

NH2
H2N NH2 HO NH2

(a) (b)

NH2 NH2
HO OH

(c) (d)

OH

O O O
CHO (i) 2eq. NaOMe / ∆
(ii) NaOH / ∆
53. 2EtO OEt + Identify product?
CHO
COOH
COOH
O O
(a) (b)
O O
HOOC
COOH
 organic reaction mechanisms and reagents 8.45

COOH
COOH
O
O
(c) (d)
O
HOOC O
HOOC

H3C O
CHO H2C (i) NaOMe / ∆
54. + Identify product?
H3C CH3

O O
O

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

CH3 H3C CH3

Cl
HC O
NaOD / D2O
55. S Identify product?
Dioxane
CH2 O

CH2 O D
(a) S (b) (c) (d)

CH2 O D

CH3

CH2 KH 18- Crown- 6 / THF Identify product?

56.
CH2
H3C
HO
8.46 chapter eight

CH3
CH3

(a) (b)

H3C
H3C
O
O
HO OH

(c) (d)

OH

OH Conc. H2SO4
57. Identify product?

OH

CH3

(a) (b)

O O
CH3

(c) (d)

H3C O
O

CH3
Conc. H2SO4
58. H C Identify product?
3
O
CH3
CH3
(a) (b)
O CH3
O
CH3
H3C CH3
H3C CH3
(c) (d)
O CH3
O
CH3
 organic reaction mechanisms and reagents 8.47

H3C O
Conc. H2SO4
59. Identify product?
CH3
CH3
H3C CH3
H3C CH3
(a) (b)
H3C CH3
H3C CH3
CH3
CH3
CH3 CH3

(c) (d)

H3C CH3

CH3
Ph
CH3 Ph
H2C P
Ph
60. Identify product?
RLi / ∆
O O

CH3
CH3
CH3
CH3
(a) (b)

O O
O
CH2

CH3 CH3

CH3 CH3
(c) (d)

H2C H2C

(i) CH2N2
(ii) NaH
61. Identify product?
(iii) MeI

O
8.48 chapter eight

(a) (b)

MeO OMe OMe

H3C H3C

(c) (d)

MeO OMe

O
(i) MeMgCl
(ii) HClO4 (aq.)
62. Identify product?
(iii) NaOH (aq.)
H3C O CH3

OH OH

H3C CH3
(a) (b)

HO OH OH

(c) (d)

OH H3C CH3

O
AcO O
O Aq. NaOH /∆
63. Identify product?

H3C CH3 CH3

O O
(a) (b)

H3C CH3 H3C

O
(c) (d)
 organic reaction mechanisms and reagents 8.49

Ac2O
64. Identify product?

H3C CH3
OH

(a) (b)
CH3
CH3
CH3
CH3

OAc OAc

(c) (d)

CH3
CH3 CH3

O
OH

65. NaOH Identify product?

H3C

O2N

O COOH
O

(a) (b)
H3C
H3C
O2N NO2

COOH COOH

(c) (d)

COOH
NO2 NO2

8.50 chapter eight

COOH
NaBH4
66. 'A' product
O2N LiAlH4
C H 'B' product
O
Identity true statement for A and B products.
OH
CH2OH

(a) ‘A’ is (b) ‘B’ is

H2N H2N
CH2OH
OH
OH
COOH

(c) ‘A’ is (d) ‘B’ is

OH O2N
O2N
OH

O (i) HO
OH (i) PPh3
H (ii) NH2NH2 / OH– /∆ (ii) BuLi
(A) (B)
(iii) H3O+ MeO OMe
67. (iv) LiAlH4
O (v) SOCl2 (iii) H

O
(iv) H3O+
Identify correct statement for (A) and (B) products.
O

Cl
(a) Structure of ‘A’ is (b) Structure of ‘B’ is

(c) Structure of ‘A’ is (d) Structure of ‘B’ is

Cl
 organic reaction mechanisms and reagents 8.51

O (i) HO OH
(ii) PPh3 CH2
68. Major product is?
(iii) H3 O+

O
O CH2 PPH3 O

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

CH2 O O O

(i) mCPBA
(ii) LAH
O O
(iii)
69. OEt / H+
O
Major product is?
(iv) LAH
(v) H3O+
O O
O OH
(a) (b) OEt (c) (d)

OH OH

70. Identify correct reaction sequence

O
NO2 NH2 OH
C OEt
LiAlH4
(a) (b) LiAlH4

C H C H
O C H
O OH
O
O O
NO2 NH2
O NaBH4 O
(c) (d) Sn + HCl

O OH
71. Identify correct reaction sequence
O O O
(a) (b)
Pd / C Ni
H2 H2

O OH O
(c) (d) (i) HS
LiAlH4 SH/H+
(ii) Ni / H2
8.52 chapter eight

72. Identify correct reaction sequence

NO2 NH2 NO2 NO2

Zn–Hg NH2 –NH2

(a) (b)
HCl OH– /∆

C Me C Me
O O
NO2 NO2 NO2 NH2

NaBH4 LiAlH4
(c) (d)

O HO O HO

73. Identify correct reaction sequence

Cl
Cl Pd / BaSO4 C
(a)
H2
O O

H
Cl Pd / BaSO4 C
(b)
H2 O
O

Cl Ni / H2
(c)
O OH

Cl LiAlH4
(d)
OH
O

CHO
(i) MeOH / H+
H OH (ii) HIO4
74. Major product is?
H OH (iii) NaBH4

CH3OH

O O
(a) (b)
MeO OMe HO OMe

MeO O OMe O OMe

(c) (d)
HO OH HO OH
 organic reaction mechanisms and reagents 8.53

COOH
(i) Br2, NaOH
75. (ii) MeOH / H+
Major product is?
(iii) NaOMe
O
O
COOH
(a) (b) C OMe

O
O
COOMe
(c) (d)
COOMe
COOMe

O O (i) 2 eq. NaOEt

(ii) Me–I
76. Major product is?
OEt (iii) Cat. NaOEt /∆
O

O
(a) (b)

O O O
O
O
(c) (d)

O O

(i) MeOH
(ii) Red P + Br2
77. Major product is?
(iii) NH3 (excess)
O O O
(iv) H3O+

COOH NH2
(a) (b)
NH2 HOOC COOH

COOH HOOC COOH

(c) (d)
NH2 NH2 NH2

(i) 2 eq. LDA

O
(ii) 2 eq. Br
78.
OEt Major product is?
(iii) O3 / Zn
(iv) OH– /∆
8.54 chapter eight

O O O O

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

COOEt COOEt O

(i) 2eq. CN
(ii) H3O+
(iii) MeOH / H+
79. Me NH2 Major product is?
(iv) NaOMe / MeOH
(v) H3O+ /∆

O O O O

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

N N N N
Me Me Me Me

OMe
(i) NaOMe
O
80. COOMe Major product is?
N (ii) Aq. NaOH
Active (iii) H+ /∆(CO2↑)
'H' H

O
(a) N (b) O (c) (d)
N
O N
O

O
H
81. Me ΟΗ–
+ Major product is?
∆
OH O
[Intramolecular aldol]
O
O
(a) (b)

O O
O
(c) (d)

O
 organic reaction mechanisms and reagents 8.55

82. O LAH Major product is?

O
t-Bu
HO
O
(a) t-Bu (b) HO
O

O
O
H C
(c) (d)

(i) LDA
(ii) 1-Bromopentane
83. Major product is?
(iii) BH3– THF
(iv) MeCOOD
H D D H
(a) (b)

D H
(c) (d)

H D

(i) H3PO4 /∆
(ii) BH3 – THF
(iii) H2O2 / OH
84. OH Major product is?
(iv) SOCl2
N
(v) NaSMe
Me Me Me
(a) OH (b) (c) (d)
SMe SMe SMe

(i) 2 eq. NaNH2

(ii) Pd / BaSO4 / H2
Br
85. (iii) OsO4, then NaHSO3
Major product is?
(iv) HIO4
Br (v) H2CrO4
8.56 chapter eight

Br O

(a) Br (b) OH

O
COOH
(c) O (d)
COOH
O

(i) BuLi
(ii) I
86. OH Major product is?
(iii) NaNH2
(iv) CH3–I
(v) Br2 / CCl4

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

(i) H2SO4
(ii) NaNH2
(iii) I
87. HO Major product is?
(iv) H3O+
(v) H2 / Lindlar’s catalyst
(vi) m·CPBA

O
O
(a) (b)
OH

O OH
O
(c) (d)
HO HO
 organic reaction mechanisms and reagents 8.57

(i) Conc. nH2SO4 / ∆

O
(ii) BuLi
88. OH H C H
Major product is?
(iii) Pd / BaSO4 / H2
(iv) Zn–Cu / CH2 I2 ether
OH O

O OH
(a) (b) O (c) (d)

89. Which of the following structures is the product from the self-condensation of two
molecules of pentan-3-one?
O O

(a) (b)

O O

(c) (d)

O H
(i) HO–(CH2)2–OH, H+
90. Major product is?
OMe O (ii) Excess MeMgBr, then H3O+

O
O OH OH O OH O
(a) (b) (c) (d)
MeO Me H

CH3 (i) Na, NH3

91. C C Major product is?
(ii) HBr
H Br Br

(a) C C CH3 (b)

H H
H H Br
(c) C C CH3 (d)

Br H
8.58 chapter eight

O
(i) Mg, Ether
O Br (ii) EtOH
92. Major product is?
(iii) Catalytic H+, H2O

H OH
OEt OEt
(a) O (b) O

O H

(c) O OH (d) O

93. Select all of the following statements about the cross Aldol experiment that are true:
(a) The ketone was added to a solution containing the aldehyde and base.
(b) The reaction can be catalyzed by an acid.
(c) The electrophile is the enolate ion.
(d) The aldehyde is used in excess.

(i) SOCl2
94. CH3CO2H Major product is?
(ii) 3-Methylaniline
(iii) LiAlH4, then H3O+
H3C NH2 H3C NH2

(a) CH3 (b) CH3

O OH

H3C NH CH3
(c) (d)
H3C N
H

CH3
(i) O3, then Zn in H2O
HO OH
95. (ii) NaBH4
(iii) Excess PBr3 O O
(iv) Excess KCN
(v) H+, H2O, Heat
Identify reactant?
CH3 CH3 CH3 CH2
(a) (b) (c) (d)
 organic reaction mechanisms and reagents 8.59

H3C OH

96. (i) HO–CH2CH2–OH, Catalytic H+ O

(ii) Mg, THF then H2O=O, then H3 O+
(iii) H3O+, heat
Identify reactant?
O
Br
H
(a) CH3 (b)

Br O

H
Br
(c) O (d)
O
Br

(i) Ph3P, then n-BuLi

97.
(ii) Cyclohexanone
(iii) CH2I2, Zn–Cu
Identify reactant?

OH O Br NH2

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

OH
98. BrMg–(CH2)4–MgBr
then, H3O+ OH

Identify reactant?
O O
O O
(a) (b) (c) (d)
O
O OEt O
O

CH2CH3 CH2CH3
Br2 H Br Br H
H Br + Br H
99.
CH3 CH3
(50:50 of these enantiomers)
Identify reactant?
8.60 chapter eight

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

(i) LDA
(ii) CH3I
100. O Major product is?
(iii) NaBH4/MeOH

O OH OH
OH3C
(a) (b) (c) (d)

(i) HBr (dark, N2)

101. (ii) PH3P, then nBuLi Major product is?
O
(iii)

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

OH

(i) (CH3CO)2O/AlCl3
102. Major product is?
(ii) Zn/Hg HCl
(iii) CH3Cl/ AlCl3
O

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

O
(i) HOCH2CH2OH/H+/heat
103. H CO2CH2CH3 Major product is?
(ii) LiAlH4, then H3O+
(iii) H3O+ / heat

O OH OH
(a) (b)
HO
H

OH O OH OH
(c) (d)
OH3C
 organic reaction mechanisms and reagents 8.67

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
c d c c c a b b b a d b c b a
16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
a c d c b c d b b c b d a b a
31 32 33 34 35 36 37 38 39 40 41 42 43 44 45
d c a b a b b c c c a b a b b
46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
d b b c d c a a c d b a a b b
61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
b d a c b bc ad b c bcd ad abcd bcd d b
76 77 78 79 80 81 82 83 84 85 86 87 88 89 90
c d b a b a b a cd d b c a b c
91 92 93 94 95 96 97 98 99 100 1 01 1 02 1 03
c d abd d b a c d d d a c a