54 - Organic Chemistry

Question

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.

 

Step-by-Step Solution

Answer

a

b

c

d

Hofmann elimination reaction

It involves the formation of the less substituted alkene that is known as the Hofmann product. It is an elimination reaction.

 

Steps involved in the reaction

a

The given compound has only one stereogenic center that is labeled as follows.

                                    Stereogenic center

b

The amides that can be reduced to form benzphetamine are mentioned below.

                       Amides that can be reduced

c

The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are mentioned below.

                       Carbonyl compound and amine

d

The reaction is shown below.

                                 Product formation