Question

Draw both organic products of the following reaction. Hint:There will be two deuterium atoms in the benzyl alcohol product.

Answer 1

Concepts and reason

The reaction of an ester is given with ${\rm{LiAl}}{{\rm{D}}_4}$ and the product needs to be drawn. ${\rm{LiAl}}{{\rm{D}}_4}$ is a strong reducing agent and thus, the given reaction is a reduction reaction.

Fundamentals

Esters on reaction with ${\rm{LiAl}}{{\rm{D}}_4}$ undergo reduction and are reduced to corresponding alcohols. The intermediate product formed is an aldehyde which is then further reduced to alcohols since the ${\rm{LiAl}}{{\rm{D}}_4}$ is a very strong reducing agent.

The intermediate aldehyde formed is as follows:

The asterisk denotes that it is an intermediate.

The further reduction of the aldehyde formed takes place and the first product is as follows:

The ethoxide ion formed in the earlier step also gains a proton and thus, the second product is as follows:

Ans:

The products of the given reaction are as follows: