- A

- B

- C

- D

View written solutionFree
Correct answer: C
- Identify the first reaction: Reimer–Tiemann reaction
-Cresol is -methylphenol. When phenols react with chloroform in alkaline medium, they undergo the Reimer–Tiemann reaction, introducing a formyl group () mainly at the ortho position to .
So, -cresol gives:
(One ortho position is equivalent to the other due to symmetry in -cresol.)
- Addition of HCN to aldehyde
Aldehyde reacts with HCN to form a cyanohydrin:
Thus,
The carbon bearing and is attached to four different groups:
- aryl group
So this carbon is stereogenic.
- Acidic hydrolysis of cyanohydrin
On acidic hydrolysis, the nitrile group converts into carboxylic acid :
Therefore the final product is:
This is an -hydroxy acid.
- Why is it chiral?
The carbon containing is attached to:
- substituted aryl group
All four groups are different, so the acid is chiral.
- Required structure
Hence the carboxylic acid must be:
with substituents corresponding to the product from ortho-formylation of -cresol, i.e. 2-hydroxy-5-methylmandelic acid.
So the correct option is C.
- Comparison with stored answer
Stored correct answer: C
Derived answer: C
They agree.
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