Question

The reduction of camphor by sodium borohydride followed by acid workup with dilute hydrochloric acid produces two isomeric alcohol products. Drag and drop the labels to complete the sketches of both products.

Answer 1

Concepts and reason

A reaction is given with the reactant, that is, camphor, whose correct major and minor product needs to be formed. Camphor is a bridged compound and undergoing a reduction reaction with sodium borohydride. Thus, consider the groups attached to the ring and major product will be formed based on the site which provide lesser steric hindrance to the incoming reagent.

Fundamentals

Bridged compounds basically contain two or more rings with the formation of a bridge. Sodium borohydride is a mild reducing agent which reduces carbonyl group into alcohol.

Draw the structure of the possible products formed by the given reaction as shown below:

Identify the major and minor product from the products drawn in step 1 as follows:

The major and minor product can be identified by knowing the mechanism of the reaction. Hydride ion from sodium borohydride will attack from the less hindered side to form the major product.

Ans:

Hence, the major and minor products can be shown as follows: