The structure shown below is that of one of the geometric isomers (the E- isomer) of the antidepressant, Doxepin: C= CH₂CH₂N(CH₂)2 E-Doxepin Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the C=C double bond in Doxepin as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of Doxepin shown above is defined as the E-isomer. In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter18: Aromaticity
Section: Chapter Questions
Problem 26CTQ
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Answer ALL parts of this question.
The structure shown below is that of one of the geometric isomers (the
E- isomer) of the antidepressant, Doxepin:
(a)
(b)
CH₂CH₂N(CH3)2
H
E-Doxepin
Explain how the Cahn Ingold Prelog sequence rules can be used to
rank groups in order of priority, using the four groups attached to the
C=C double bond in Doxepin as illustrations.
Based on the order of priority of the four groups determined in part (a)
of this question, explain why the isomer of Doxepin shown above is
defined as the E-isomer.
(c)
In general terms, explain why this isomer might have different effects in
the human body from its geometric isomer.
Transcribed Image Text:Answer ALL parts of this question. The structure shown below is that of one of the geometric isomers (the E- isomer) of the antidepressant, Doxepin: (a) (b) CH₂CH₂N(CH3)2 H E-Doxepin Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the C=C double bond in Doxepin as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of Doxepin shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.
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