question_answer

Match the compounds given in list I with list II and select the suitable option using the code given belows.

List-I	List-II
A. Benzaldehyde	1. Phenolphthalein
B. Phthalic anhydride	2. Benzoin condensation
C. Phenyl benzoate	3. Oil wintergreen
D. Methyl salicylate	4. Fries rearrangement

Code

A) A-4         B-1         C-3         D-2

B) A-4         B-2         C-3         D-1

C) A-2         B-3         C-4         D-1

D) A-2         B-1         C-4         D-3

Correct Answer: D

Solution :

[a] Benzoin condensation. When an ethanolic solution of benzaldehyde is heated with strong alkali like KCN or NaCN, we get benzoin. \[\text{2}{{\text{C}}_{\text{6}}}{{\text{H}}_{\text{5}}}-\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\text{H}\xrightarrow[{}]{\text{C}{{\text{N}}^{\text{ }\!\!\Theta\!\!\text{ }}}}{{\text{C}}_{\text{6}}}{{\text{H}}_{\text{5}}}\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\underset{\text{benzoin}}{\mathop{\underset{\begin{smallmatrix}  \text{ }\!\!|\!\!\text{ } \\  \text{OH} \end{smallmatrix}}{\mathop{\text{CH}}}\,}}\,-{{\text{C}}_{\text{6}}}{{\text{H}}_{\text{5}}}\] [b] Formation of phenolphthalein. When phenol is treated with phthalic anhydride in the presence of concentrated \[{{\text{H}}_{\text{2}}}\text{S}{{\text{O}}_{\text{4}}}\text{,}\]it gives phenolphthalein, an indicator. [c] Fries rearrangement Phenyl benzoate when heated with anhydrous \[AlC{{l}_{3}}\] in the presence of inert solvent gives ortho-and para-hydroxybenzophenone.    In    this rearrangement, there is a benzoyl group migration from the phenolic oxygen to an ortho-and para-position. (A chief constituent of oil of wintergreen)