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JEE Main levelNumerical answerDifficulty 2 of 3o4251

The alcohol shown is dehydrated with acid. Assume no rearrangement and count E and Z isomers as different compounds. How many distinct alkenes can form? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 5

The alcohol is 3-methylhexan-3-ol and gives a tertiary cation. Loss of H from the methyl gives 2-ethylpent-1-ene (1). Loss from the ethyl CH2 gives (E)- and (Z)-3-methylhex-2-ene (2), and loss from the propyl CH2 gives (E)- and (Z)-3-methylhex-3-ene (2). The total is 1 + 2 + 2 = 5.
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