Question
Using curved arrow notation, show the formation of reactive intermediates when the following covalent bonds undergo heterolytic cleavage.
  1. $\text{CH}_3-\text{SCH}_3$
  2. $\text{CH}_3-\text{CN}$
  3. $\text{CH}_3-\text{Cu}$

Answer

  1. $\text{CH}_3-\text{SCH}_3\leftrightarrow\text{C}^-\text{H}_3+\stackrel{+}{\text{SCH}_3}$
  2. $\text{CH}_3-\text{CN}\leftrightarrow\stackrel{+ \ \ \ \ \ }{\text{CH}_3}+\text{CN}^-\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{\text{Carbocation}}$
  3. $\text{CH}_3-\text{Cu}\leftrightarrow\text{C}^-\text{H}_3+\text{Cu}^+\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{\text{Carbonion}}$

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