Chapter 17, Problem 17.81P

Interpretation Introduction

Interpretation:

The mechanism for the reaction is to be proposed to account for the formation of the product described in the data from the $\text{C}\text{ NMR}$_and its IR spectrum.

Concept introduction:

Sodium borohydride is a reducing agent and is a source of hydride ions (${\text{H}}^{\text{-}}$). Sodium borohydride (${\text{NaBH}}_{\text{4}}$) is used to reduce aldehyde and ketone in the presence of protic solvents. The product of an aldehyde is a primary alcohol, but in some cases, the intramolecular nucleophilic substitution reaction takes place, when the substrate possesses a good leaving group. In such a case, some different product is formed instead of the alcohol. In the IR spectrum, the peak near ${\text{1700 cm}}^{\text{-1}}$ is the characteristic peak due to the carbonyl group stretching, and the broad peak above ${\text{3000 cm}}^{\text{-1}}$ is due to the $\text{O-H}$ stretching. A peak above ${\text{3000 cm}}^{\text{-1}}$ is because of the ${\text{sp}}^{\text{2}}$ and $\text{sp}$ $\text{C-H}$ stretching.

The $\text{C}\text{ NMR}$ spectrum suggests the number of distinct carbon atoms for the given compound.