The Riemer Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol, ortho to the hydroxyl group. This reaction involves electrophilic aromatic substitution. This is a general method for the synthesis of substituted salicylaldehydes as depicted below

Which one of the following reagents is used in the above reaction?

aq. $N a O H + C H_{3} C l$

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aq. $N a O H + C H_{2} C l_{2}$

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aq. $N a O H + C H C l_{3}$

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aq. $N a O H + C C l_{4}$

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Solution

The correct option is C
aq. $N a O H + C H C l_{3}$

The first steps is that of the formation of dichlorocarbene via $α$ elimination:

The dichlorocarbene is electron deficient and the activated phenoxide is electron-rich:

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