Organic Compounds Containing Halogens Question 110
Question: When phenol reacts with $ CHCl_3 $ and KOH, the product obtained would be
[RPMT 1997]
Options:
A) Salicylaldehyde
B) p-hydroxy benzaldehyde
C) Both A and B
D) Chloretone
Show Answer
Answer:
Correct Answer: C
Solution:
It is an example of Riemer-Tiemer Reaction. First, base will help to form phenoxide. Also, the base will remove Hydrogen and one chlorine atom from $CHCl_3$ by taking H+ , will finally leads to leaving of Cl-, whivh forms $CCl_2$(carbene).
Carbene attaches to Phenoxide on Ortho position. Then the intermediate formed does SN2 with the base.
The new intermediate reacts with Hydronium to form Salicylalydehyde and some amount of P-hydroxy benzaldehyde
BETA
