Question

Question: Draw the products formed when each alcohol undergoes dehydration with TsOH , and label the major product when a mixture results.

a.

b.

c.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Step-by-Step Solution Step 1: Reaction of alcohol with TsOH

TsOH is used to convert alcohol into alkenes. It is known as “dehydration of alcohol” and it is regioselective. The products of the reaction are formed according to the Zaitsev rule.

After the elimination of -OH and -H atoms, there would be two alkenes formed. The major product will be trisubstituted, and the minor will be disubstituted alkene

Formation of the products

a. The reaction of 2,6-dimethylheptan-4-ol with TsOH results in the formation of (E)-2,6-dimethylhept-3-ene. The reaction is shown below.

Formation of the product in a

b. The reaction of pentan-3-ol with TsOH results in the formation of two products, as shown below.

Formation of the product in b

c. The reaction of 1-methylcyclohexanol with TsOH results in the formation of two products, as shown below.

Formation of the product in c