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Chapter 11: Q60. (page 453)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

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: Answer the following questions about erlotinib and phomallenic acid C. Erlotinib, sold under the trade name Tarceva, was introduced in 2004 for the treatment of lung cancer. Phomallenic acid C is an inhibitor of bacterial fatty acid synthesis.

a. Which C-H bond in erlotinib is most acidic?

b.What orbitals are used to form the shortest C-C single bond in erlotinib?

c. Which H atom in phomallenic acid C is most acidic?

d. How many sp hybridized carbons are contained in phomallenic acid C?

e. Rank the labelled bonds in phomallenic acid C in order of increasing bonds strength.

Question: Draw the enol tautomer of (a) and the keto tautomer of (b).

a.

b.

Which bases can deprotonate acetylene? The pKa values of the conjugate acids are given in parentheses.

Question: Ignoring stereoisomers, draw the two possible enols for butan-2-one (CH3COCH2CH3), and predict which one is more stable.

Question: What reactions are needed to convert alcohol A into either alkyne B or alkyne C?
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