FUNDAMENTALS OF BIOCHEMISTRY - LL FD
FUNDAMENTALS OF BIOCHEMISTRY - LL FD
5th Edition
ISBN: 9781119598022
Author: Voet
Publisher: WILEY
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Chapter 9, Problem 1E
Summary Introduction

To determine: Whether trans-oleic acid has a higher or lower melting point than cis-oleic acid.

Concept introduction: An oleic acid is a colorless and odorless fatty acid. It occurs naturally in different animal and vegetable fats and oils. In its triglyceride form, oleic acid is used as a component in many foods. As they are part of the animal fats and vegetable oils, oleic acid can be used as components in normal human diet.

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Answer to Problem 1E

Answer: Trans-oleic acid has a higher melting point than cis-oleic acid.

Explanation of Solution

Explanation:

Trans isomers have a higher melting point compared to cis isomers. It is mainly because of the less-stearic hindrance of trans isomers. Trans-oleic acids have a melting point of 44.5°C and cis-oleic acids have a melting point of 13.4°C. The trans isomer of oleic acid is able to pack together easier because of less stearic hindrance.  However, it is difficult to pack the cis isomer together due to its higher stearic hindrance. The cis isomer has a “U” shape but the trans isomer is more planar. This allows for better packing in trans isomers. Due to all these reasons, trans-oleic acid has a higher melting point than cis-oleic acid.

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