Q7-63E - Organic Chemistry (Mcmurry)

Question

Retin A, or retinoic acid, is a medication commonly used to reduce wrinkles and treat severe acne. How many different isomers arising from double-bond isomerizations are possible?

Step-by-Step Solution

Answer

There are 16 isomers of Retin A arising from double-bond isomerizations.

Step 1: Isomerizations

Isomerization is the process of the conversion of compounds into their isomeric forms. The number of isomers arising from double-bond isomerization is calculated using 2ⁿ, where n is the number of double bonds present in the compound.

Step 2: Different isomers arising from double-bond isomerizations.

In Retin A, there are five carbon-carbon double bonds. The double bonds present in the ring cannot isomerize. So, Retin A can have 2⁴ =16 isomers, where four double bonds are present outside the ring.

                                                                  Retin A