Chapter 22: Q1P (page 1151)
Phenylacetone can form two different enols.
- Show the structures of these enols.
- Predict which enol will be present in the larger concentration at equilibrium.
Short Answer
a.

b.

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Chapter 22: Q1P (page 1151)
Phenylacetone can form two different enols.
a.

b.

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Without looking back, propose a mechanism for the hydrolysis of this iminium salt to the alkylated ketone. The first step is attack by water, followed by loss of a proton to give a carbinolamine. Protonation on nitrogen allows pyrrolidine to leave, giving the protonated ketone.
Predict the major products of the following reactions.
b)

Propose a mechanism for the acid-catalyzed bromination of pentan-3-one.
Predict the products of self-condensation of the following esters.
(a) methyl propanoate +
(b) ethyl phenylacetate + NaOCH2CH3
(c)

(d)

Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with pyrrolidine.
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