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Chapter 25: PROBLEM 25.27 (page 1027)

Question: Draw the product formed by treating each compound with excess CH3I , followed by Ag2O, and then heat.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Hoffmann elimination 

In Hofmann elimination, the base removes a proton from the less substituted and more accessible αcarbon atom, because of the bulky leaving group on the nearby alpha carbon.

The bulky leaving group is obtained as quaternary ammonium salt by the attack of the amine to the methyl iodide via SN2 reaction.

02

Explanation

a. The reaction of the given amine is completed via the Hoffmann elimination process as:

Hoffmann elimination in compound a.

b.The given amine produces the product alkene via the Hoffmann elimination process as:

Hoffmann elimination in compound b.

c. The given amine produces the product alkene via the Hoffmann elimination process as:

Hoffmann elimination in compound c.

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Most popular questions from this chapter

Question: What starting materials are needed to prepare each drug using reductive amination? Give all possible pairs of compounds when more than one route is possible.

a.

b.

What amide(s) can be used to prepare each amine by reduction?

(a)

(b)

(c)

Rank the following compounds in order of increasing basicity and explain the order you chose.

Question: Devise a synthesis of each compound from benzene.

a.

b.

c.

d.

Question: Give a systematic or common name for each compound.
See all solutions

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