Question

Question: Draw the products of each reaction.

a.

b.

c.

d.

Short answer

Answer

a.

b.

c.

d.

Step-by-step solution

Step-by-Step Solution Step 1: Reaction of alcohol with sodium hydride

Alcohol treated with sodium hydride or sodium amide leads to the formation of alkoxide nucleophiles.

Formation of the products in a and b

a. The reaction of propan-1-ol with sodium hydride results in the formation of sodium propan-1-olate and hydrogen gas. The reaction is shown below.

Formation of the product in a

b. The reaction of 1-cyclopentylethanol with sodium amide results in the formation of sodium 1-cyclopentylethanolate and ammonia, as shown below.

Formation of the product in b

Formation of the products in c and d

c. The reaction of hexan-2-ol with NaH followed by bromopropane results in the formation of 2-propoxyhexane and NaBr, as shown below.

Formation of the product in c

d. The reaction of 2-bromocyclohexanol with sodium hydride results in the formation of 7-oxabicyclo[4.1.0]heptane as shown below.

Formation of the product in d