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Chapter 30: Problem 694

Trimyristin is a white crystalline fat, m.p. \(54-55^{\circ}\), obtainable from nutmeg, and is the principal constituent of nutmeg butter. Hydrolysis of trimyristin with hot aqueous sodium hydroxide gives an excellent yield of myristic acid, m.p. \(52-53^{\circ}\), as the only fatty acid. What is the structure of trimyristin?

Short Answer

Expert verified
The structure of trimyristin can be determined by analyzing the hydrolysis reaction with hot aqueous sodium hydroxide, which produces myristic acid as the only fatty acid. The structure of trimyristin consists of three myristic acid molecules and a glycerol molecule, connected through ester linkages. The resulting structure can be written as: \(\mathrm{CH_3(CH_2)_{12}COOCH_2CH\left(OOC(CH_2)_{12}CH_3\right)CH_2OOC(CH_2)_{12}CH_3}\).

Step by step solution

01

Understanding Hydrolysis

Hydrolysis is a chemical reaction wherein a molecule gets split due to the reaction with water. In this exercise, hydrolysis of trimyristin results in the formation of myristic acid and another product. The hydrolysis of esters, for instance, occurs when a molecule reacts with water, causing the ester to break apart into its constituent parts.
02

Identifying the Ester Functional Group

Given that the only fatty acid produced during this reaction is myristic acid, we can presume that trimyristin contains three myristic acid molecules as these are what remain after the hydrolysis process. Myristic acid has the structural formula: \(\mathrm{CH_3(CH_2)_{12}COOH}\) Since trimyristin is the ester of three myristic acid molecules, we need to determine what the other part of the molecule is. Esters are formed through the reaction between a carboxylic acid and an alcohol, producing the ester and water. Given that there are three myristic acid molecules, we can assume that the alcohol used has three hydroxy groups (\(\mathrm{-OH}\)).
03

Identifying the Alcohol

The most common alcohol with three hydroxy groups is glycerol, which has the structural formula: \(\mathrm{HOCH_2CH(OH)CH_2OH}\) This would make the hydrolysis reaction as follows: Trimyristin + 3H₂O -> 3Myristic Acid + Glycerol
04

Deriving the Structure of Trimyristin

Now that we have identified the ester functional group and have determined that glycerol is the other part of the molecule, we can draw the structure of trimyristin. The ester functional group is formed by combining the carboxylic acid group of the myristic acid and the hydroxy group of glycerol, resulting in the following ester linkage: \(\mathrm{CH_3(CH_2)_{12}COO-CH_2}\) There will be three of these ester linkages to account for the fact that there are three myristic acid molecules. The structure for trimyristin would therefore be: \(\mathrm{CH_3(CH_2)_{12}COOCH_2CH\left(OOC(CH_2)_{12}CH_3\right)CH_2OOC(CH_2)_{12}CH_3}\)

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Most popular questions from this chapter

Spermaceti (a wax from the head of the sperm whale) resembles high-molecular weight hydrocarbons in physical properties and inertness toward \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\) and \(\mathrm{KMnO}_{4} ;\) on qualitative analysis it gives positive tests only for carbon and hydrogen. However, its infrared spectrum shows the presence of an ester group, and quantitative analysis gives the empirical formula \(\mathrm{C}_{16} \mathrm{H}_{32} \mathrm{O}\) A solution of the wax and \(\mathrm{KOH}\) in ethanol is refluxed for a long time. Titration of an aliquot shows that one equivalent of base has been consumed for every \(475 \pm 10\) grams of wax. Water and ether are added to the cooled reaction mixture, and the aqueous and ethereal layers are separated. Acidification of the aqueous layer yields a solid \(\mathrm{A}\), m.p. \(62-3^{\circ}\), neutralization equivalent \(260 \pm 5\). Evaporation of the ether layer yields a solid B, m.p. \(48-9^{\circ}\). Reduction by LiAlHi \(_{4}\) of either spermaceti or A gives \(B\) as the only product. B is normal alcohol. What is the structure of spermaceti?

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