Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 23, Problem 10PP
Interpretation Introduction

Interpretation:

The different chirality centers of cholesterol are to be marked with an asterisk.

Concept Introduction:

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The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.

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A pair of two mirror images which are non-identical is known as enantiomers which are optically active.

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The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.

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The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

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Diastereomers are the stereoisomers that are not mirror images of each other and are not superimposable on each other.

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They possess different physical as well as chemical properties, because of difference in orientations.

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Cholesterol is an organic compound and a derivative of steroid. In the human body, it is produced as an intermediate in the biosynthesis of steroids. It is produced at a much higher rate than what is necessary for the synthesis of steroid. In a molecule of cholesterol, there is no internal plane of symmetry, and hence every carbon atom is different and each chiral carbon has four different groups.

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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. cleavage Bond A •CH3 + 26.← Cleavage 2°C. + Bond C +3°C• CH3 2C Cleavage E 2°C. 26. weakest bond Intact molecule Strongest 3°C 20. Gund Largest argest a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. C Weakest bond A Produces Most Bond Strongest Bond Strongest Gund produces least stable radicals Weakest Stable radical b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 13°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. • CH3 methyl radical Formed in Gund A Cleavage c.…
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