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Chapter 24: Problem 5

Spermaceti is a wax obtained from the sperm whale. It contains, among other materials, an ester known as cetyl palmitate, which is used as an emollient in a number of soaps and cosmetics. The systematic name for cetyl palmitate is hexadecyl hexadecanoate. Write a structural formula for this substance.

Short Answer

Expert verified
The structural formula for cetyl palmitate is 颁贬鈧�(CH鈧�)鈧佲倕O-C(=O)-(颁贬鈧�)鈧佲倓颁贬鈧�.

Step by step solution

01

Understand the Name

The systematic name 'hexadecyl hexadecanoate' provides valuable information about the structure of the ester. In IUPAC nomenclature, the name is divided into two parts: the alkyl group and the acid portion. 'Hexadecyl' refers to the 16-carbon alkyl chain, and 'hexadecanoate' refers to the ester derived from palmitic acid, which has 16 carbon atoms.
02

Draw the Alkyl Group

Start by drawing the 'hexadecyl' part, which is a saturated hydrocarbon chain with 16 carbon atoms. It is represented as 颁贬鈧�(颁贬鈧�)鈧佲倓颁贬鈧傗垝, where 颁贬鈧� is the terminal methyl group, and CH鈧� is repeated 14 times.
03

Draw the Acid-Derived Part

Next, draw the 'hexadecanoate' part, which is derived from hexadecanoic acid (palmitic acid). As an ester, it consists of a -C(=O)O- group attached to a 16-carbon chain, represented as 颁鈧佲倕贬鈧冣倎颁(=翱)翱鈭�.
04

Combine the Components

Combine the hexadecyl group and hexadecanoate group through an ester bond. The ester bond forms between the oxygen of the hexadecyl (-O-) and the carbon of the carbonyl group of hexadecanoate (C(=O)). The complete structure is 颁贬鈧�(CH鈧�)鈧佲倕O-C(=O)-(颁贬鈧�)鈧佲倓颁贬鈧�.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

IUPAC Nomenclature
In chemistry, IUPAC nomenclature is the standardized system for naming chemical compounds. It ensures clear communication of compound structures. For cetyl palmitate, its formal name is hexadecyl hexadecanoate. This name helps chemists understand the exact composition by breaking it down into two key parts:

  • First part - "Hexadecyl": This indicates a 16-carbon atom chain forming the alkyl group.
  • Second part - "Hexadecanoate": This represents the ester derived from hexadecanoic (palmitic) acid.
By analyzing names given by IUPAC, chemists can determine structures without seeing the actual molecule, aiding in understanding and synthesizing chemical compounds effectively.
Thus, cetyl palmitate, with its systematic name, provides all necessary information for its structural formulation.
Hexadecyl Group
The hexadecyl group is an important component in the structure of cetyl palmitate. It consists of a long saturated hydrocarbon chain, specifically 16 carbon atoms in length. This group is represented in the chemical formula as 颁贬鈧�(颁贬鈧�)鈧佲倓颁贬鈧傗垝.

Each part of the formula tells us more about the structure:
  • 颁贬鈧�: This represents the terminal methyl group at one end of the chain.
  • (颁贬鈧�)鈧佲倓: This denotes the repeating methylene groups, making up the central portion of the chain.
  • 颁贬鈧傗垝: This part connects to the ester group in the molecule.
Such saturated chains are common in fats and waxes, providing hydrophobic properties. Understanding the hexadecyl group helps when visualizing cetyl palmitate's full structure and its behavior in different environments.
Hexadecanoate Group
The hexadecanoate group in cetyl palmitate derives from hexadecanoic acid, known commonly as palmitic acid. This part of the molecule contains an ester group and a long carbon chain.

Its structural components include:
  • 颁(=翱)翱鈭�: This denotes the ester linkage where the oxygen atom connects to the hexadecyl group.
  • 颁鈧佲倕贬鈧冣倎: This chain continues from the ester linkage and represents the fifteen carbon atoms connected with hydrogen atoms.
The hexadecanoate portion forms a crucial part of esters like cetyl palmitate. It is responsible for the emulsifying and conditioning properties of the ester. Knowing this section of the molecule allows better understanding of how cetyl palmitate functions, especially in applications like cosmetics where smooth and evenly distributed textures are desired.

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Most popular questions from this chapter

Isoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3 -dibromo-3-methylbutane. Write a series of equations describing the mechanism of this reaction.

Describe an efficient synthesis of each of the following compounds from octadecanoic (stearic) acid using any necessary organic or inorganic reagents: (a) Octadecane (b) 1-Phenyloctadecane (c) 3-Ethylicosane (d) Icosanoic acid (e) 1-Octadecanamine (f) 1-Nonadecanamine

What fatty acids are produced on hydrolysis of 2-oleyl-1,3-distearylglycerol? What other triacylglycerol gives the same fatty acids and in the same proportions as 2-oleyl-1,3-distearylglycerol?

Give the structure of the keto acyl-ACP formed after four cycles of chain extension starting with acetyl-ACP.
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