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JEE Main levelNumerical answerDifficulty 2 of 3o3018

Eight halides are heated separately in 80% aqueous ethanol at with no added strong nucleophile: 2-chloro-2-methylpropane, chlorodiphenylmethane, bromobenzene, 3-bromo-3-methylpentane, bromoethene, iodomethane, 1-bromo-1-methylcyclohexane and 1-bromobutane. For how many of them is substitution by the unimolecular SN1 pathway the dominant route? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 4

SN1 needs a reasonably stable carbocation. The tertiary halides (2-chloro-2-methylpropane, 3-bromo-3-methylpentane, 1-bromo-1-methylcyclohexane) and the diaryl-stabilised chlorodiphenylmethane qualify, giving 4. Bromobenzene and bromoethene would need aryl or vinyl cations, and iodomethane and 1-bromobutane would give methyl or primary cations, so they do not react by SN1. The count is 4.
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