Which of the following sets of reactions cannot give a carboxylic acid as the final product?

R M g X + O = C = O d r y e t h e r - ---- \to (A) H_{3} O^{+} - -- \to (B)

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P h - C H_{2} - C H_{2} - C H_{3} i) K M n O_{4} / O H^{-}, △ - ----------- \to i i) H_{3} O + (A)

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C H_{3} (C H_{2})_{8} C H_{2} O H H_{2} S O_{4} - --- \to C r O_{3} (A)

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R - C \equiv N i) S n C l_{2} / d i l . H C l - ---------- \to (A) i i) H_{2} O / H^{+} - ------ \to (B)

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Solution

The correct option is D $R - C \equiv N i) S n C l_{2} / d i l . H C l - ---------- \to (A) i i) H_{2} O / H^{+} - ------ \to (B)$
(a)
$R M g X + O = C = O d r y e t h e r - ---- \to R - O | | C (A) - O M g X H_{3} O + - --- \to R - O | | C (B) - O H$

(b) This is Stephen's reaction for aldehyde synthesis.
$R - C \equiv N i) S n C l_{2} / d i l . H C l - ---------- \to R - C H = N H_{2}^{+} C l^{-} (A) i i) H_{2} O / H^{+} - ------ \to R - C H O (B) + N H_{4} C l$

(c)
$P h - C H_{2} - C H_{2} - C H_{3} i) . K M n O_{4} / O H^{-}, △ - ------------ \to i i) . H_{3} O + P h - C O O H (A)$

(d) Jones reagent oxidises primary alcohol to the corresponding carboxylic acid.

$C H_{3} (C H_{2})_{8} C H_{2} O H H_{2} S O_{4}, a c e t o n e - -------- \to C r O_{3} C H_{3} (C H_{2})_{8} C O O H (A)$

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