The major product [B] in the following reactions is: (see structure) $\xrightarrow[\text { Heat }]{\mathrm{HI}}[\mathrm{A}]$ alcohol $\xrightarrow[\Delta]{\mathrm{H}_{2} \mathrm{SO}_{4}}[\mathrm{~B}]$

(D) $\mathrm{CH}_{2}=\mathrm{CH}_{2}$

JEE Main · 2020 · 04 Sep 2020 · Shift 2 · Alcohols Phenols and Ethers

The major product [B] in the following reactions is:

(see structure)

HI Heat [A]

alcohol

H_{2} SO_{4} Δ [B]

(A)(see structure)
(B)(see structure)
✓ Correct
(C)(see structure)
(D) $CH_{2} = CH_{2}$

Answer: (B)

Solution

Heating the ether with

HI

cleaves it at the less hindered

C - O

bond to give an alcohol

[A]

, which on warming with concentrated

H_{2} S O_{4}

undergoes acid-catalysed dehydration. Elimination follows Saytzeff's rule, so the proton is lost from the carbon that yields the more substituted, more stable alkene, and that most-substituted alkene is the major product

[B]

JEE Main · 2020 · 04 Sep 2020 · Shift 2 · Single correct option

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