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Chapter 26: Problem 1

How many constitutional isomers are possible for a triglyceride containing one molecule each of palmitic acid, oleic acid, and stearic acid?

Short Answer

Expert verified
Answer: There are 6 possible constitutional isomers for such a triglyceride.

Step by step solution

01

Understand the molecular structure of glycerol and fatty acids

Glycerol has three hydroxyl groups (-OH) that can form ester bonds with the three fatty acids. Palmitic, oleic, and stearic acids are fatty acids with the following number of carbon atoms: palmitic acid (16 carbons), oleic acid (18 carbons), and stearic acid (18 carbons). Note that oleic acid has one double bond and stearic acid has no double bonds, making them different fatty acids despite having the same number of carbons.
02

Calculate the number of ways to attach the fatty acids to glycerol

There are three positions on the glycerol molecule where the fatty acids can be attached. We can consider the fatty acids as distinct entities and calculate the number of unique arrangements possible. There are 3! (3 factorial) ways to arrange these fatty acids around the glycerol molecule, which is equal to 3 × 2 × 1 = 6.
03

Determine if any of these arrangements are identical

Since the glycerol molecule has identical hydroxyl groups, the arrangement of fatty acids does not matter when they are connected to different positions on the glycerol molecule. Therefore, the number of constitutional isomers remains 6.
04

Report the number of constitutional isomers

There are 6 possible constitutional isomers for a triglyceride containing one molecule each of palmitic acid, oleic acid, and stearic acid.

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Most popular questions from this chapter

Identify the hydrophobic and hydrophilic region(s) of a triglyceride.

Lecithins can act as emulsifying agents. The lecithin of egg yolk, for example, is used to make mayonnaise. Identify the hydrophobic part(s) and the hydrophilic part(s) of a lecithin. Which parts interact with the oils used in making mayonnaise? Which parts interact with the water? Fat-Soluble Vitamins

Draw a structural formula for methyl linoleate. Be certain to show the correct configuration of groups about each carbon-carbon double bond.

What is meant by the term hardeningas applied to vegetable oils?

Palmitic acid (hexadecanoic acid) is the source of the hexadecyl (cetyl) group in the following compounds. Each is a mild surface-acting germicide and fungicide and is used as a topical antiseptic and disinfectant. They are examples of quaternary ammonium detergents, commonly called "quats." Cetylpyridinium chloride Benzylcetyldimethylammonium chloride (a) Cetylpyridinium chloride is prepared by treating pyridine with 1-chlorohexadecane (cetyl chloride). Show how to convert palmitic acid to cetyl chloride. (b) Benzylcetyldimethylammonium chloride is prepared by treating benzyl chloride with \(N, N\)-dimethyl-1-hexadecanamine. Show how this tertiary amine can be prepared from palmitic acid.
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