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 9PP
Interpretation Introduction

Interpretation:

The three-dimensional formula for androsterone and norethynodrel is to be given.

Concept Introduction:

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Androsterone, a secondary male sex hormone, is an endogenous steroid hormone. It is a weak androgen with a molecular formula of C19H30O2.

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The structure of androsterone consists of four rings, three six membered carbon rings and one five membered carbon ring. It consists of a hydroxyl group at the third carbon atom, two methyl groups at the tenth and the thirteenth carbon positions respectively, and a ketone group at the seventeenth carbon position.

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Norethynodrel is a group of synthetic steroids having functions similar to those of progesterone. These are widely used as oral contraceptives; however, now have been discontinued. Its molecular formula is C20H26O2.

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The structure of norethynodrel consists of three six membered carbon ring and one five membered carbon ring. It consists of a hydroxyl group at the third carbon atom, two methyl groups at the tenth and the thirteenth carbon positions respectively, and a ketone group at the seventeenth carbon position.

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(11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond 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. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)!
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