Question

Question: Draw the products of each reaction, and indicate the stereochemistry at any stereogenic center.

a.

b.

Short answer

Answer

a.

b.

Step-by-step solution

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

The treatment of alcohol with TsCl in the presence of pyridine results in the formation of alkyl tosylates. The tosylate group is a good leaving group as its conjugate base is strong.The treatment of alcohol with TsCl in the presence of pyridine results in the formation of alkyl tosylates. The tosylate group is a good leaving group as its conjugate base is strong.

Formation of the product in a

a. The reaction of butan-1-ol with TsCl in the presence of pyridine results in the formation of butyl 4-methylbenzenesulfonate, as shown below.

Formation of the product in a

Formation of the product in b

b. The reaction of (R)-pentan-2-ol with TsCl in the presence of pyridine results in the formation of (R)-pentan-2-yl 4-methylbenzenesulfonate, as shown below.

Formation of the product in b