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Chapter 7: PROBLEM 7.79 (page 295)

Question: Draw a stepwise mechanism for the following reaction sequence.

Short Answer

Expert verified

A ketone is represented by the functional group -CO-. The carbonyl carbon is an electrophilic center of the ketone where the nucleophile can attack.

Step by step solution

01

Ketone

A ketone is represented by the functional group -CO-. The carbonyl carbon is an electrophilic center of the ketone where the nucleophile can attack.

02

Chemical properties of ketone

The ketone also contains acidic hydrogen adjacent to the carbonyl carbon. Therefore, a base can abstract and form the carbanion.

03

Explanation

In the given reaction, the acidic hydrogen of hexanone is abstracted by the given base NaH. Therefore, the carbanion delocalizes its electrons. The two resonating structures give the two products.

The major product is formed by the pi donation of an electron to the methylbromide.

The minor product is formed by the oxide donation of electrons to the methylbromide.

Representation of the first step

Representation of the second step

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Most popular questions from this chapter

Question: Which compound in each pair reacts faster in nucleophilic substitution?

a.

b.

c.

d.

Question: Draw the product of each SN2 reaction and indicate stereochemistry.

a.

b.

Question: Which solvents favor SN1reactions and which favor SN2 reactions?

a.

b. CH3CN

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Question: Draw the products of each SN1 reaction and indicate the stereochemistry when necessary.

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b.

Question: Rank the following carbocations in order of increasing stability.

a.

b.

c.
See all solutions

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