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Choose the Best Answer · Q9

Q.(CH3)3C-CH(OH)-CH3 --Conc. H2SO4--> X (major product). X is (as printed in the textbook, options

(c) and
(d) are the same structure)
a) (CH3)3C-CH=CH2
b) (CH3)2C=C(CH3)2
c) CH2=C(CH3)-CH2-CH2-CH3
d) CH2=C(CH3)-CH2-CH2-CH3
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Step 1. (CH3)3C-CH(OH)-CH3 is 3,3-dimethylbutan-2-ol; protonation and loss of water first gives a SECONDARY carbocation at C2 (flanked by the bulky tert-butyl group).

Step 2. A 1,2-METHYL SHIFT from the adjacent tert-butyl carbon converts this secondary cation into a more stable TERTIARY carbocation. …

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