JEE Main 2016 · 3 Apr · Shift 1 · Chemistry Q54

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ChemistrySingle correct+4 / -1Question 54 of 90

2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields :

(a) $\ce{C2H5CH2C(CH3)2OCH3}$ (b) $\ce{C2H5CH2C(CH3)=CH2}$ (c) $\ce{C2H5CH=C(CH3)CH3}$

All of these

(a) and (c)

(a) and (b)

Answer and worked solution

Official answer: A

A tertiary chloride with methoxide in methanol gives mainly elimination, both the Hofmann alkene (b) and the more substituted Saytzeff alkene (c), together with some substitution product (a), the methyl ether formed by solvolysis. So all three form.

Topics:Elimination reactions SN1 and SN2

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JEE Main 2016 · 3 Apr · Shift 1, Chemistry question 54