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Question

Using the curved-arrow notation, show the formation of reactive intermediates when the following covalent bonds undergo heterolytic cleavage:
a. CH3SCH3
b. CH3CN
c. CH3Cu

A
a. CH3SCH3CH3+SCH3;
b. CH3CNCH3+CN;
c. CH3CuCH3+Cu
(Cu is more electropositive than C).
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B
a. CH3SCH3CH3+SCH3;
b. CH3CNCH3+CN;
c. CH3CuCH3+Cu
(Cu is more electropositive than C).
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C
a. CH3SCH3CH3+SCH3;
b. CH3CNCH3+CN;
c. CH3CuCH3+Cu
(Cu is more electropositive than C).
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D
a. CH3SCH3CH3+SCH3;
b. CH3CNCH3+CN;
c. CH3CuCH3+Cu
(Cu is more electronegative than C).
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Solution

The correct option is A a. CH3SCH3CH3+SCH3;
b. CH3CNCH3+CN;
c. CH3CuCH3+Cu
(Cu is more electropositive than C).
a). In the heterolytic cleavage, the carbon atom will bear positive charge and the S atom will bear negative charge.
CH3SCH3CH3+SCH3

b). In the heterolytic cleavage, the methyl carbon atom will bear positive charge and the cyanide carbon atom will bear negative charge.
CH3CNCH3+CN

c). In the heterolytic cleavage, the methyl carbon will bear negative charge and the copper will bear positive charge. This is because Cu is more electropositive than C.
CH3CuCH3+Cu

Option A is correct.

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