Chapter 21, Problem 21.52SP

An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57 °C. The IR spectrum of trimyristin shows a very strong absorption at 1733 cm⁻¹. Basic hydrolysis of trimyristin gives 1 equivalent of glycerol and 3 equivalents of myristic acid (tetradecanoic acid).

1. a. Draw the structure of trimyristin.
2. b. Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts.