CHEM1280 Problem Set 8

(Due on 28 Nov., 2012)

1. Give the products of each of the following reactions:

2. Propose a reasonable synthesis of the following compounds starting from cyclohexanone

and any compound that has no more than 3 carbon atoms. More than one step may be
necessary. Indicate the reaction condition for each step and show two methods for
compound b.

3. Propose a mechanism for the following reaction:

4. Draw the enol tautomers for each of the following compounds. If the compound has more
than one enol tautomer, indicate which one is more stable.

5. What compound is formed when a dilute solution of cyclohexanone with NaOD in D2O is
shaken for several hours?
6. As shown below, a β,γ-unsaturated carbonyl compound rearranges to a more stable
conjugated α,β-unsaturated compound in the presence of a base. Propose a mechanism for
the following base-catalyzed rearrangement.

7. Propose a reasonable mechanism for the following reaction.