Amine Chemistry

Please see the attached file for the fully formatted problems.

1. Which reaction sequence would be best to prepare m-chloroaniline from benzene?

a. chlorination, nitration, reduction
b. nitration, reduction, chlorination
c. nitration, chlorination
d. nitration, chlorination, reduction
e. nitration, reduction, acetylation, chlorination, hydrolysis
2. To convert nitrobenzene, C6H5NO2, to acetanilide, ,the correct synthetic sequence employs:

a. (CH3CO)2O, then Sn/HCl
b. Sn/HCl, then CH3COOH
c. Sn/HCl, then (CH3CO)2O
d. CH3COOH at 180°, then Sn/HCl
e. Sn/HCl, then NaNO2/HCl, then (CH3CO)2O
3. Which sequence represents the best synthesis of 4-isopropylbenzonitrile?

a.
1. Benzene + (CH3)2CHCl, AlCl3
2. Br2, FeBr3
3. KCN

b.
1. Benzene + (CH3)2CHCl, AlCl3
2. HNO3, H2SO4
3. Fe, HCl
4. NaOH
5. NaNO2, HCl, H2O
6. CuCN

c.
1. Benzene + (CH3)2CHCl, AlCl3
2. HNO3, H2SO4
3. Fe, HCl
4. NaOH
5. KCN

d.
1. Benzene + HNO3, H2SO4
2. (CH3)2CHCl, AlCl3
3. Fe, HCl
4. NaOH
5. NaNO2, HCl, H2O
6. CuCN

e.
1. Benzene + HNO3, H2SO4
2. Fe, HCl
3. NaOH
4. NaNO2, HCl, H2O
5. CuCN
6. (CH3)2CHCl, AlCl3
4. Which one of the following is a primary amine?

a. 2-Methyl-2-butanamine
b. N-Methyl-1-butanamine
c. N-Methyl-2-butanamine
d.
e.
5. Which of the following compounds may be hydrolyzed to give propylamine, CH3CH2CH2NH 2?

a. 1
b. 2
c. 3
d. 4
6. Which one of the following compounds gives diethylamine, (CH3CH2)2NH, on reduction with lithium aluminum hydride?

a. 1
b. 2
c. 3
d. 4
7. What is an acceptable name for CH3CH2CH2CH2NHCH3?

a. 1-Methylbutylamine
b. N-Butylmethylamine
c. N-Methylbutylamine
d. 2-Pentanamine
8. Which one of the following classes of compounds is not reduced by catalytic hydrogenation?

a. Aldehyde
b. Alkene
c. Carboxylic acid
d. Nitrile
e. Nitro
9. Which of the following routes would be best for the synthesis of m-bromoaniline from benzene?

a. 1
b. 2
c. 3
d. 4
e. 5
10. Which of the following sequences would be suitable for the preparation of m-bromophenol (E)?

a. 1
b. 2
c. 3
d. 4