Question 57

Given below are two statements:
Statement I: The dipole moment of R-CN is greater than R-NC and R-NC can undergo hydrolysis under acidic medium to produce $$O\\||\\R-C-OH$$.

Statement II: R-CN hydrolyses under acidic medium to produce a compound which on treatment with $$SOCl_{2}$$, followed by the addition of $$NH_{3}$$ gives another compound(x). This compound (x) on treatment with NaOCl/NaOH gives a product, that on treatment with $$CHCl_{3}/KOH/ \Delta$$ produces R-NC

In the Light of the above statements, choose the correct answer from the options given below

We need to evaluate two statements about R-CN and R-NC.

Statement I: "The dipole moment of R-CN is greater than R-NC and R-NC can undergo hydrolysis under acidic medium to produce RCOOH."

The dipole moment of R-NC is actually greater than R-CN (isocyanides have higher dipole moments due to the lone pair on carbon and formal charges). Also, R-NC on hydrolysis gives R-NH₂ + HCOOH, not RCOOH.

Statement I is FALSE.

Statement II: "R-CN hydrolyses under acidic medium to produce RCOOH, which on treatment with SOCl₂ gives RCOCl, then with NH₃ gives RCONH₂ (compound x). Treatment of RCONH₂ with NaOCl/NaOH (Hofmann bromamide degradation) gives R-NH₂. Then R-NH₂ + CHCl₃/KOH/Δ (carbylamine reaction) gives R-NC."

Let's trace the sequence:

R-CN → (H₃O⁺) → RCOOH → (SOCl₂) → RCOCl → (NH₃) → RCONH₂ (compound x)

RCONH₂ → (NaOCl/NaOH, Hofmann degradation) → RNH₂

RNH₂ → (CHCl₃/KOH/Δ, carbylamine reaction) → RNC

This sequence is correct. Statement II is TRUE.

Therefore, Statement I is false but Statement II is true, which corresponds to Option 1.

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