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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 伪carbon 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: Label the stereogenic centers in each compound.

a.

b.

Devise a synthesis of each compound from benzene, any organic alcohols having four carbons or fewer, and any required reagents.

a

b

c

Question: Draw the product of each reaction.

a.

b.

c.

d.

Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex

  1. Label the stereogenic center(s).
  2. What amide(s) can be reduced to form benzphetamine?
  3. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods.
  4. What products are formed by Hofmann elimination from benzphetamine? Label the major product.

Question: Draw the products of each acid鈥揵ase reaction. Indicate whether equilibrium favors the reactants or products.

a.

b.

c.
See all solutions

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