Question

The major products X and Y formed in following reaction sequence are

• A. A
• B. B
• C. C
• D. D

Hint:

Pyrrole with CHCl$_3$/KOH gives chloropyridine by Ciamician-Dennstedt rearrangement, and NaNH$_2$ substitution on halopyridines may proceed through cine-substitution

Answer 1

The Correct Option is C

Step 1: Identify the first reaction.
Pyrrole reacts with CHCl$_3$/KOH through Ciamician-Dennstedt rearrangementThis reaction causes ring expansion of pyrrole to give chloropyridine

Step 2: Formation of product X.
In this rearrangement, pyrrole is converted mainly into 3-chloropyridine
\[ \text{Pyrrole} \xrightarrow{\text{CHCl}_3,\text{ KOH}} \text{3-chloropyridine} \]

Step 3: Reaction of X with NaNH$_2$.
3-Chloropyridine reacts with NaNH$_2$ through elimination-addition mechanism involving pyridyne intermediate

Step 4: Formation of product Y.
Due to cine-substitution, the amino group enters adjacent to the position from where chlorine was removedTherefore, 3-chloropyridine gives 4-aminopyridine as the major product
\[ \text{3-chloropyridine} \xrightarrow{\text{NaNH}_2} \text{4-aminopyridine} \]

Step 5: Conclusion.
Thus, X is 3-chloropyridine and Y is 4-aminopyridine
\[ \boxed{\text{C}} \]