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Chapter 11: Q60. (page 453)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Mechanism for the given reaction

Step by step solution

01

Step-by-Step SolutionStep 1: Acid-catalyzed keto-enol tautomerism

The acid-catalyzed keto-enol tautomerism takes place in two steps:

The first step involves the protonation of the double bond to form the resonance-stabilized carbocation.

The next step involves the loss of protons to form the carbonyl group. As a result of the reformation of acid in the second step, the tautomerization is acid-catalyzed.

02

The stepwise mechanism for the given acid-catalyzed reaction.

The given reaction takes place in the following steps:

Mechanism for the given reaction

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Most popular questions from this chapter

Question: Synthesize each compound from acetylene. You may see any other organic or inorganic reagents.

a.

b.

c.

d.

e.

Question: Tautomerization in base resembles tautomerization in acid, but deprotonation precedes protonation in the two-step mechanism. (a) Draw a stepwise mechanism for the following tautomerization. (b) Then, draw a stepwise mechanism for the reverse reaction, the conversion of the keto form to the enol.

Give the IUPAC name for each compound.

a.

b.

c.

d.

Question: Devise a synthesis of each compound. You may use HC≡CH , ethylene oxide, and alkyl halides as organic starting materials and any inorganic reagents.

a.

b.

Question: The alkyl halides must be methyl or $1 °$

a.

b.

c.

See all solutions

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