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.

Better nucleophile 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?

a.

b.

c.

d.

e.

f.

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

a.

b.
 c.

d.

6. Which stereoisomer would be obtained in greater yield from an E2 reaction of each of the
following alkyl halides?

a. b.

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.