Question

Predict the product(s) if the starting materials below underwent a Claisen rearrangement. Draw arrows to illustrate the rearrangement of electrons.

(a)

(b)

(c)

Short answer

The answer is

(a)

(b)

(c)

Step-by-step solution

Claisen rearrangement

The Claisen rearrangement is a reaction of unsaturated compounds that takes place in the presence of heat. It is also called the (3,3) rearrangement.

Subpart (a)

The product of the reaction is shown below.

Reaction (a)

The reaction involves the rearrangement of electrons in presence of heat to give an unsaturated cyclic ketone.

Subpart (b)

The product of the reaction is shown below.

Reaction (b)

In this reaction, rearrangement gives an unsaturated aldehyde containing Deuterium.

Subpart (c)

The product of the reaction is shown below.

Reaction (c)

The reaction involves the rearrangement of the reactant to give a cyclic unsaturated ketone.