Question

An ether extraction of nutmeg gives large quantities of triolein, a waxy crystalline solid of melting point 57 °C. The IR spectrum of triolein shows a very strong absorption at1735 cm^-1 . Basic hydrolysis of triolein gives 1 equivalent of glycerol and 3 equivalents of oleic acid ((9Z)-Octadec-9-enoic acid).

(a) Draw the structure of triolein.

(b) Predict the products formed when triolein is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.

Short answer

(a)

Formation of triolein

(b)

Formation of desired products

Step-by-step solution

Triolein

(a) Triolein is an asymmetrical triglyceride that is formed by the reaction of glycerol with an unsaturated fatty acid, i.e., oleic acid. It is used in the textile industry for textile finishing.

Structure of triolein

The structure of triolein is represented as follows:

Formation of triolein

The reaction of triolein with lithium aluminum hydride

(b) Triolein is a triglyceride that reacts with lithium aluminum hydride used for reduction in the presence of water to form glycerol and primary alcohol as the by-product.

Formation of products

The products formed by the reaction of triolein with lithium aluminum hydride is represented as follows:

Formation of desired products