Chapter 20, Problem 20.12YT

Interpretation Introduction

Interpretation:

A way to draw the missing curved arrows and to identify the tetrahedral intermediate is to be determined.

Concept introduction:

${\text{LiAlH}}_{\text{4}}$ is a stronger reducing agent and will reduce a carboxylic acid to a primary alcohol. ${\text{LiAlH}}_{\text{4}}$ reduces an amide (${\text{RCONR}}_{\text{2}}$) to an amine (${\text{RCH}}_{\text{2}}{\text{NR}}_{\text{2}}$), preserving the overall carbon backbone of the original compound. It is particularly striking that the product is an amine, because ${\text{LiAlH}}_{\text{4}}$ reduces all of the other acid derivatives to primary alcohols.