What will be the major product when m-cresol is reacted with propargyl bromide (HC\(\equiv\)C–CH2Br) in presence of K2CO3 in acetone?
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The Correct Option is A
Solution and Explanation
The phenoxide ion is a good nucleophile and attacks the CH2 carbon of propargyl bromide in an SN2 (Williamson ether synthesis) reaction in polar aprotic acetone, displacing Br-.
Product: 1-methyl-3-(prop-2-yn-1-yloxy)benzene, the aryl propargyl ether with CH3 meta to the O-CH2-C≡CH group.
Options (2), (3) and (4) are ring C-propargylated free phenols (Claisen-type products that need heat) and are not formed here. Option (1) shows the ether.
Answer: (1) the aryl propargyl ether (m-CH3-C6H4-O-CH2-C≡CH)
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