Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 22, Problem 22.9P
Interpretation Introduction
Interpretation:
Explanation for the preferential
Expert Solution & Answer
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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.…
Br.
COOH Br,
FCH COOH E
FeBr
ASOCI
B
NH
(CH,CO),OD Br₂
2
C
alcKOH
Find A to F (all)
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 22.1PCh. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3PCh. 22.2 - Prob. 22.4PCh. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8PCh. 22 - Prob. 22.9PCh. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...
Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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