Using the curved-arrow notation, show the formation of reactive intermediates when the following covalent bonds undergo heterolytic cleavage: a. CH3−S−CH3 b. CH3−CN c. CH3−Cu
A
a. CH3↷−S−CH3→⊕CH3+⊖SCH3; b. CH3↷−CN→⊕CH3+⊖CN; c. ↶CH3−Cu→⊖CH3+⊕Cu (Cu is more electropositive than C).
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B
a. CH3↶−S−CH3→⊖CH3+⊕SCH3; b. CH3↷−CN→⊕CH3+⊖CN; c. ↶CH3−Cu→⊕CH3+Cu (Cu is more electropositive than C).
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C
a. CH3↷−S−CH3→⊕CH3+⊖SCH3; b. CH3↷−CN→⊕CH3+⊖CN; c. ↷CH3−Cu→⊖CH3+Cu (Cu is more electropositive than C).
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D
a. CH3↷−S−CH3→⊕CH3+⊖SCH3; b. CH3↷−CN→⊕CH3+⊖CN; c. ↶CH3−Cu→⊕CH3+Cu (Cu is more electronegative than C).
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Solution
The correct option is A a. CH3↷−S−CH3→⊕CH3+⊖SCH3; b. CH3↷−CN→⊕CH3+⊖CN; c. ↶CH3−Cu→⊖CH3+⊕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. CH3↷−S−CH3→⊕CH3+⊖SCH3
b). In the heterolytic cleavage, the methyl carbon atom will bear positive charge and the cyanide carbon atom will bear negative charge. CH3↷−CN→⊕CH3+⊖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.