Reactions of Aldehydes and Ketones

Please see the attached file for the fully formatted problems.
1. Which one of the following compounds reacts with cyclopentanone to yield an imine?

a. NaNH2
b. (CH3)2CHNH2
c. (CH3)3N
d. (CH3)2NH
2. Which one of the following reacts with ethylmagnesium bromide to form a chiral alcohol?

a. Acetone
b. 2-Butanone
c. Acetaldehyde (ethanal)
d. Propanal
e. Cyclopentanone
3. What is the principal product of the following reaction?

a. 1
b. 2
c. 3 - I guessed; if wrong - please correct and explain; if correct - still, please explain
d. 4
e. 5
4. What is the IUPAC name for the compound shown?

a. 4-Benzyl-4-isopropropylbutanal
b. 4-Isopropyl-4-phenylbutanal
c. 4-Benzyl-5-methylhexanal
d. 2-Methyl-3-phenylhexanal
e. 5-Methyl-4-phenylhexanal
5. How would you prepare the alcohol shown below?

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

6. The product (C) of the following reaction sequence is:

a. Butanal
b. 1-Butanol
c. 2-Butanol
d. 2-Methyl-1-propanol
e. 2-Methyl-2-propanol
7. What sequence of steps represents the best synthesis of 2-heptanol?

a. CH3CH2CH2MgBr (2 moles) + formaldehyde in diethyl ether followed by H3O+
b. CH3CH2CH2MgBr + butanal in diethyl ether followed by H3O+
c. CH3CH2CH2CH2MgBr + acetone in diethyl ether followed by H3O+
d. CH3CH2CH2CH2CH2MgBr + ethanal in diethyl ether followed by H3O+
8. Which of the following will reduce an aldehyde to a primary alcohol?

a. NaBH4
b. CH3MgBr
c. PCC
d. H2CrO4
e. HCN

9. Which one of the following best represents the flow of electrons in the key step for the aldol addition reaction that occurs when propanal is treated with sodium hydroxide?

a. 1
b. 2
c. 3
d. 4
e. 5
10. The reaction of sec-butylmagnesium bromide with formaldehyde followed by hydrolysis yields:

a. 2,2-Dimethyl-1-pentanol
b. 2-Butanol
c. 2-Methyl-1-butanol
d. 2-Pentanol
e. 2,2-Dimethyl-1-propanol