1.

At first glance the conversion of bromobenzene to benzenitrile looks simple just cary out a nucleophilic substitution using cyanide ion as the nucleophile. Then we remember that bromobenzene does not undergo either an S_(N)1 or an S_(N)2 reaction (Section 6.14A). The conversion can be accomplishes. however. thogh it involves severals steps. Outline possible steps.

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