ORGANIC CHEMISRTY(LL)W/CONNECT
ORGANIC CHEMISRTY(LL)W/CONNECT
5th Edition
ISBN: 9781260100228
Author: SMITH
Publisher: MCG
Question
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Chapter 31, Problem 31.14P
Interpretation Introduction

(a)

Interpretation: A skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called “andro,” from the given description is to be drawn.

Concept introduction: Steroids, a group of tetracyclic lipids composed of one five-membered ring and three six-membered rings. These rings are lettered by A, B, C, and D. Most of the steroids contain two angular methyl groups. These methyl groups are numbered as C18 and C19 respectively.

Interpretation Introduction

(b)

Interpretation: The addition of all wedges and dashed wedges for all stereogenic centers to steroid 4-androstene-3,17-dione with the given information are to be stated.

Concept introduction: Steroids, a group of tetracyclic lipids composed of one five-membered ring and three six-membered rings. These rings are lettered by A, B, C, and D. Most of the steroids contain two angular methyl groups. These methyl groups are numbered as C18 and C19 respectively.

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(a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl at C17, a double bond between C1 and C2, and methyl groups bonded to C1, C10, and C13. (b) Add wedges and dashed wedges for all stereogenic centers with thefollowing information: the configuration at C10 is R, the configuration at C13 is S, the configuration at C17 is S, and all substituents at ring fusions are trans to each other. (c) Draw the structure of Primobolan, the product formed  when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.
Draw a complete structure for vanillin showing all C atoms, H atoms, andlone pairs, and give the molecular formula. Vanillin is the principalcomponent of the extract of the vanilla bean. ?
Draw the structure of cholic acid, showing the rings in their chairconformations, and label each methyl group and hydroxy group asaxial or equatorial.

Chapter 31 Solutions

ORGANIC CHEMISRTY(LL)W/CONNECT

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