Practice Exam on S_N2 and S_N1 Reactions

1. Show an arrow pushing mechanism for the solvolysis reaction below. (6 pts)

2. Considering your knowledge of SN2 reactions and leaving group ability, predict the major product of the following reactions. (4 pts)

3. The following solvolysis reaction gives 2 diastereomeric ethers.

a. Circle the major product. (3 pts)

4. Is the following reaction faster in acetonitrile (CH3CN) or methanol (CH3OH)? ___________ (3 pts)

5.Which reaction occurs faster in ethanol? a or b (2 pts) _________

6. (9 pts) Rank the following by writing the numbers 1, 2, or 3 in the blanks.

a. stability: 1 = most stable, 3 = least stable

b. rate of SN1 reaction: 1 = fastest, 3 = slowest

7. Circle the stronger Nucleophile in DMSO:

(8 pts)

a. CH₃OH or CH₃O^-

b. NH₂^- or OH^-

c. CH₃COO^- or CH₃O^-

d. CH₃O^- or CH₃S^-