Question

Question: Prepare each compound from cyclopentanol. More than one step may be needed.

a.

b.

c.

d.

Short answer

Answer

a.

b.

c.

d.

Step-by-step solution

Step-by-Step SolutionStep 1: Reactions of cyclopentanol

The cyclic compound with five carbon atoms and attached with the hydroxyl group is referred to as cyclopentanol.

The functional group –OH does not act as a good leaving group, and by using suitable reagents and the reaction conditions, the desired product can be obtained.

Explanation

a. To substitute the –OH group with the –Cl group, the suitable reagent is either HCl or ${\mathrm{SOCl}}_2$in pyridine.

b. The alkene from alcohol can be produced by a dehydration reaction. For this reaction, the suitable reagent is${\mathrm{H}}_2{\mathrm{SO}}_4$ .

c. The alcohol group can be converted into the ether by first converting the alcohol to alkoxide and then reacting with an alkyl halide.

d. The alcohol group can be substituted with ${\mathrm{CN}}^{-}$by reacting it with the reagent TsCl (tosyl chloride) in pyridine and then with sodium cyanide

The product of the given reaction

a.

Conversion from cyclopentanol into compound a

.

b.

Conversion from cyclopentanol into compound b

c.

Conversion from cyclopentanol into compound c

d.

Conversion from cyclopentanol into compound d