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← IIT-JEE 2011 · Paper 2
ChemistrySingle correct+3 / -1Question 7 of 60

IIT-JEE 2011 · Paper 2, Chemistry question 7

The major product of the following reaction is

3,4-Dihydro-2H-pyran treated with RCH₂OH and H⁺ (anhydrous).
Choose one option
Answer and worked solution

Official answer: B

Mechanism. Protonation of the enol-ether double bond of 3,4-dihydro-2H-pyran gives an oxocarbenium ion at C-2. The alcohol attacks it, and loss of HX+\ce{H+} gives a 2-alkoxytetrahydropyran (a THP ether).

Product type. C-2 carries two OR groups (ring O and OCHX2R\ce{OCH2R}): an acetal. This is the standard THP protection of alcohols.

(B)