8th Edition

ISBN: 9781337516402

Author: Brown

Publisher: Cengage

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Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compound…

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Textbook Question

Chapter 21, Problem 21.64P

Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen.

Chapter 21, Problem 21.64P, Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is , example 1

Chapter 21, Problem 21.64P, Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is , example 2

(a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed.
(b) Discuss the chemical logic behind the use of each blocking group in this synthesis.
(c) Propose a mechanism for the conversion of D to E.
(d) Propose a mechanism for the conversion of F to toremifene.
(e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?

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Chapter 21, Problem 21.63P

Chapter 22.1, Problem 22.1P

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Chapter 21 Solutions

Organic Chemistry

Ch. 21.2 - Construct a Frost circle for a planar...Ch. 21.2 - Which compound gives a signal in the 1H-NMR...Ch. 21.2 - Prob. 21.3P Ch. 21.2 - Prob. 21.4P Ch. 21.3 - Prob. 21.5P Ch. 21.4 - Arrange these compounds in order of increasing...Ch. 21.4 - Prob. AQ Ch. 21.4 - Prob. BQ Ch. 21.4 - Prob. CQ Ch. 21.5 - Prob. 21.7P

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Solution Summary: The author explains the structural formula for benzyl and tetrahydropyranyl group, and the chemical logic for each blocking group.

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Chapter 21 Solutions