Question

Show how you would use anhydrides to synthesize the following compounds. In eachcase, explain why an anhydride might be preferable to an acid chloride.

(a) n-octylformate

Short answer

Answer

The use of anhydride to synthesize the given compound is given below.

Step-by-step solution

formation of n-octylformate

• When acetic formic anhydride reacts with n-octyl alcohol, there is a formation of n-octylformate.

Acetic formic anhydride, formed from sodium formate and acetyl chloride, reacts primarily withthe formyl groups. The formyl group is less hindered and more electrophile than the acetyl group. So, when n-octyl alcohol is formylated by acetic formic anhydride, it formsa formic ester called n-octylformate.

Step 2:Anhydride might be preferable to an acid chloride in the given reaction.

• The anion of an acid is an excellent leaving group. Hence, anhydride is preferred to acid chloride as formyl chloride cannot be used for formylation because it decomposes quickly to CO and HCl.