- A

- B

- C

- D

View written solutionFree
Correct answer: A
-
Identify the reaction conditions
We have m-cresol reacting with propargyl bromide in presence of in acetone.
These are standard Williamson ether synthesis conditions:
- acts as a mild base.
- It deprotonates the phenol to form cresoxide ion.
- Acetone is a polar aprotic solvent, favoring substitution.
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Formation of nucleophile
m-Cresol is:
In presence of , it forms the phenoxide:
-
Nature of electrophile
Propargyl bromide is a primary alkyl halide:
Primary halides react readily by with phenoxide ions.
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Site of attack
The phenoxide oxygen attacks the carbon of propargyl bromide via .
So the product is:
This is m-cresyl propargyl ether.
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Why not C-alkylation on the ring?
Although phenoxide activates the ring, under these conditions:
- mild base (),
- primary alkyl halide,
- polar aprotic solvent,
O-alkylation is strongly favored over ring alkylation.
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Major product
Therefore the major product is the propargyl ether of m-cresol:
-
Comparison with stored answer
The stored correct answer is A. Since the actual option structures are not shown, I infer that option A corresponds to the ether:
Hence, my derived answer agrees with the stored answer.
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