Diethylamine (DEA) reacts with l-bromobutane (BB) to form diethylbutylamine (DEBA) From the data given below (provided by N. Leininger, Univ. of Virginia), find the effect of solvent on the second-order rate constant.
Rate of reaction in acetonitrile is more than that in diol, because acetoniltrile is polar solvent and has ability to stabilize the transtion state which result in acceleration of reaction while diol is hydrogen bond donor solvent (HBD), has ability to form hydrogen bonding with nitrogen lone pair which reduce the nucleophilicity of amine therefore the rate is very slow.
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