Question

Choose the best option for the precursor to the tosylate intermediate Design a synthesis of cis-2-methylcyclopentyl acetate from trans-2-methylcyclopentanol.

Answer 1

To synthesize cis-2-methylcyclopentyl from methycyclopentanol, you need to replace the acetate hydroxyl group with acetate by inverting the configuration.

Step-by-step explanation:

To understand the process, you need to understand the nucleophilic mechanism taking place in the process. This is the first stage of the process. Hydroxide is a poor leaving group, to it must be converted to a good leaving group. To effect the change, it is necessary to use p-toluenesuphate.

p-toluenesuphate is favored because this can be prepared by a reaction that alters none of the bonds attached to the stereogenic center.

The reaction of p-toluensulfonate with potassium acetate in acetic acid effects the conversion to give the final product: cis-2-methylcyclopentyl.