Which of the following chloropyridines readily undergo nucleophilic substitution upon treatment with NaCN?
A) 2-chloropyridine
B) 3-chloropyridine
C) 4-chloropyridine
D) both A and C
E) both A and B

Question

Quizplus · Accepted Answer

2-chloropyridine and 4-chloropyridine readily undergo nucleophilic substitution due to the electron-withdrawing nature of the nitrogen in the pyridine ring, which stabilizes the negative charge in the transition state. 3-chloropyridine is less reactive due to the lack of resonance stabilization.

Which of the Following Chloropyridines Readily Undergo Nucleophilic Substitution Upon