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Consider the compound CH3CH2-C(Br)(CH3)-CH3. When this compound is treated with C2H5OH in the presence of heat, what is the major product formed?

1. CH3CH2-C(OC2H5)(CH3)-CH3
2. CH3-CH=C(CH3)2
3. CH3CH(OC2H5)CH(CH3)2
4. CH3CH2-C(=CH2)-CH3

Correct answer: CH3-CH=C(CH3)2

Solution

C2H5OH at high temperature promotes E2 elimination. Zaitsev's rule predicts the major product is the more substituted alkene, which is 2-methylbut-2-ene (CH3-CH=C(CH3)2) formed by losing HBr toward the more substituted carbon.

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