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Exercise · Q19

Q.1-Bromopropane and 2-bromo-2-methylpropane are both treated with NaOH\text{NaOH} in ethanol under conditions favouring SN2S_N2. Which reacts faster, and why?

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Under SN2S_N2-favouring conditions (here, hydroxide, a good nucleophile, in ethanol), rate depends heavily on how accessible the backside of the halogen-bearing carbon is to the incoming nucleophile. In 1-bromopropane (a primary substrate), that carbon carries only one other carbon and two hydrogens, leaving the rear face largely open for attack. In 2-bromo-2-methylpropane (a tertiary substrate), the reacting carbon is flanked by three bulky methyl groups, which sterically block the nucleophile's approach from behind almost completely. This steric hindrance dominates the rate comparison, so the primary substrate reacts very much faster by $ …

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