Question

Question: Draw the product of each reaction, indicating the stereochemistry at any stereogenic center.

b.

Short answer

Answer

a.

The nucleophile and OH are situated anti to each other.

b.

The nucleophile and OH are located anti to each other.

Step-by-step solution

Step-by-Step Solution Step 1: Reaction of epoxides

Epoxides possess a strained ring comprising two polar bonds. The nucleophilic attack opens the strained ring. Strong nucleophiles like and acids like HCl can help the reaction to take place.

Opening of epoxide ring with strong nucleophiles

The epoxide reaction involves two rules:

In the first rule, nucleophiles strike from the rear side of the epoxide. Secondly, nucleophiles possessing a negative charge strike at the carbon that is less substituted.

Products of the epoxide reaction

a. The product of this particular reaction is given below:

Product of the epoxide reaction a

The nucleophilic attack from the backside at the less substituted carbon leads to the cleavage of the C-O bond, thereby relieving the strain of the three-membered ring. In the final product, the nucleophile and OH are placed anti to each other.

b. The product of epoxide reaction b is given below:

Product of the epoxide reaction b

The C-O bond gets broken because of the nucleophilic attack from the rear side at the less substituted carbon. The nucleophile and OH are situated anti to each other in this particular reaction.