Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 30, Problem 30.1P

One component of jojoba oil is a wax formed from eicosenoic acid [ CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 9 CO 2 H ] and CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 8 OH . Draw the structure of the wax, including the cis geometry of both carbon–carbon double bonds.

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Interpretation Introduction

Interpretation: The structure of the wax formed from eicosenoic acid [CH3(CH2)7CH=CH(CH2)9CO2H] and CH3(CH2)7CH=CH(CH2)8OH, including the cis geometry of both carbon-carbon double bonds is to be stated.

Concept introduction: Waxes are lipids, which are hydrolysable. They contain ester (RCOOR') as the functional group, and obtained from alcohol (R'OH) and a fatty acids (RCOOH) of high molecular weight.

Answer to Problem 30.1P

The structure of the wax formed from eicosenoic acid [CH3(CH2)7CH=CH(CH2)9CO2H] and CH3(CH2)7CH=CH(CH2)8OH, including the cis geometry of both carbon-carbon double bonds is shown below.

Organic Chemistry, Chapter 30, Problem 30.1P , additional homework tip  1

Figure 1

Explanation of Solution

Waxes are lipids, which are hydrolysable. They contain ester (RCOOR') as the functional group, and obtained from alcohol (R'OH) and a fatty acids (RCOOH) of high molecular weight.

The treatment of eicosenoic acid [CH3(CH2)7CH=CH(CH2)9CO2H] with CH3(CH2)7CH=CH(CH2)8OH is an esterification reaction. The reaction yields ester (desired wax) as the product and H2O as the by-product.

The structure of the wax formed from eicosenoic acid [CH3(CH2)7CH=CH(CH2)9CO2H] and CH3(CH2)7CH=CH(CH2)8OH, including the cis geometry of both carbon-carbon double bonds is shown below.

Organic Chemistry, Chapter 30, Problem 30.1P , additional homework tip  2

Figure 1

Conclusion

The structure of the wax formed from eicosenoic acid [CH3(CH2)7CH=CH(CH2)9CO2H] and CH3(CH2)7CH=CH(CH2)8OH, including the cis geometry of both carbon-carbon double bonds is shown on Figure 1.

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