Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Question
Chapter 3, Problem 1EQ
Interpretation Introduction
Interpretation:
The leaving group in the given molecule is to be determined inorder identify the positively charged and negatively charged fragments produced during mechanism.
Concept Introduction:
Heterolytic cleavage of sigma bond occurs under a variety of conditions. The mechanism of bond cleavage is as shown below,
The arrow in the above mechanism indicates that the sigma electrons form A-B bond are leaving A and becoming the exclusive property of B. Since the fragment A is formally losing one electron, it must become positively charged and B must become negatively charged since it gains an electron.
Expert Solution & Answer
Answer to Problem 1EQ
The mechanism yields a negatively charged Chloride ion and positively charged isopropyl cation.
Explanation of Solution
The given Lewis structure of isopropyl chloride:
Chlorine is the leaving group in this case. As Chlorine is more electronegative, it obtains the shared electron pair during heterolytic bond cleavage as shown below.
Hence, the cleavage of isopropyl chloride yields chloride ion (negatively charged as shared electron is obtained) and isopropyl cation.
Conclusion
The positive and negative fragments produced in the mechanism are identified.
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Draw the major product of this reaction. Ignore any byproducts.
Use the dropdown menu to indicate whether the rate of the reaction shown below will increase,
decrease, or remain the same when the reaction conditions are changed to X or to Y or to Z
(see below).
NaCN
Br
CN
CH3CN
X: Change the leaving group from Br to CI
Y: Increase the concentration of haloalkane
Z: Increase the concentration of NaCN
X:
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Y:
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Chapter 3 Solutions
Pushing Electrons
Ch. 3 - Prob. 1EQCh. 3 - Prob. 2EQCh. 3 - Prob. 3EQCh. 3 - Prob. 4EQCh. 3 - Prob. 5EQCh. 3 - Prob. 6EQCh. 3 - Here are some exercises in sigma bond breaking....Ch. 3 - Prob. 8EQCh. 3 - Prob. 9EQCh. 3 - Prob. 10EQ
Ch. 3 - Prob. 11EQCh. 3 - Prob. 12EQCh. 3 - Prob. 13EQCh. 3 - Prob. 14EQCh. 3 - Prob. 15EQCh. 3 - Prob. 16EQCh. 3 - Prob. 17EQCh. 3 - Prob. 18EQCh. 3 - Prob. 19EQCh. 3 - Prob. 20EQCh. 3 - Prob. 21EQCh. 3 - Prob. 22EQCh. 3 - Prob. 23EQCh. 3 - Prob. 24EQCh. 3 - Prob. 25EQCh. 3 - Prob. 26EQCh. 3 - Prob. 27EQCh. 3 - Prob. 28EQCh. 3 - Prob. 29EQCh. 3 - Prob. 30EQCh. 3 - The reaction just described is reversible....Ch. 3 - Prob. 32EQCh. 3 - Prob. 59EQ
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