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Predict the major organic product of methylpropan-2-ol reacted with H2SO4 and a free radical substitution reaction with CH4 and heat.

Predict the major organic products for the attached reactions.


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The starting material is a tertiary alcohol, methylpropan-2-ol. This is reacted with conc. H2SO4, which in this case acts as a dehydrating agent. The product is methylpropene.

The mechanism is an E1 elimination, typical of tertiary alcohols. The H2SO4 protonates the alcohol.

Water is lost from the molecule (this is the E1 part of things) - easily because a tertiary carbocation ...

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