2-methyl-2hexanol is reacted with sulfuric acid at around 800C. The two products

Question

2-methyl-2hexanol is reacted with sulfuric acid at around 800C. The two products formed are 2-methyl-1-hexene (19%) and 2-methyl-2-hexene (81%). Show the chemical equation for this reaction. Explain fully why 2-methyl-2-hexene is the major product. (25 points)

Explanation / Answer

The method is "treating" the reactants "react" CH3(HO)C(CH3)CH2CH2CH2CH3 -------> alkene + H2O (dehydrated by H2SO4) the intermediate cation is (CH3)2C(+)CH2CH2CH2CH3; the products are ____CH3C(CH3)=CHCH2CH2CH3 (81%) CH2=C(CH3)CH2CH2CH2CH3 (19%) At the reaction temperature, the 2-ene is the more thermodynamically stable. Compare the pentane versions: dH (2-methyl-2-ene) = -14.96 kcal/mole; dH (2-methyl-1ene) = -13.56 kcal/mole

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