CHEM1280 Problem Set 6

(Due on 14 Nov. 2012)

1. For each of the following pairs, indicate which is a better nucleophile and which is a
better leaving group.

2. Rank the following alkyl bromides in order of decreasing reactivity toward the SN1
reaction with ethanol.

3. Rank the following alkyl halides in order of decreasing reactivity toward the S N2 reaction
with NaCN.

4. Starting with 1-bromobutane, how could the following compounds be prepared?

5. For each of the following reactions, give the substitution products; if the products can
exist as stereoisomers, show what stereoisomers are obtained:
a. (R)-2-bromopentane + high concentration of CH3O−
b. (R)-2-bromopentane + CH3OH
c. trans-1-bromo-4-methylcyclohexane + high concentration of CH3O−
d. trans-1-bromo-4-methylcyclohexane + CH3OH

6. Which stereoisomer would be obtained in greater yield from an E2 reaction of each of the
following alkyl halides?
7. Propose a reasonable mechanism for the following reaction to account for the formation
of the three products. Use curved arrows to show the flow of electrons.