By K.R. Desai
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A 3 0 carbocation is 340 kJ/mol more stable than a 10 carbocation! As a result, it is much easier for (CH)3CBr to form a carbocation intermediate than it is for CH3Br to undergo a similar reaction. In theory, both starting materials could undergo both reaction mechanisms. But the rate of SN2 reactions for CH3Br are much faster than the corresponding SN I reactions, whereas the rate of SN I reactions for (CH3)3CBr are very much faster than SN2 reactions. Elimination Reactions Why do we need to worry about whether a nucleophilic substitution reaction occurs by an SNI or SN2 mechanism?
Mechanism The reaction proceeds by activation of the triphenylphosphine by reaction with the tetrahalomethane, followed by attack of the alcohol oxygen at phosphorus to generate an oxyphosphonium intermediate. The oxygen is then transformed into a leaving group, Organic Reaction Mechanism 42 and an SN2 displacement by halide takes place, proceeding with inversion of configuration if the carbon is asymmetric. ~. ~ Ph 3 PI' Br cAl • Br"\" Br Br Ph Ph )~Br Ph I Ph + ~Iql Ph/~~~ Y' ARBUZOV REACTION EtO....
Why, then, does (CH3)3CBr react with the OH- ion by the SN1 mechanism if CH3Br does not? The SN 1 reaction proceeds through a carbocation intermediate, and the stability of these ions decreases in the following order. " They can donate electron density to a neighbouring group. This tends to delocalize the charge over a larger volume of the molecule, which stabilizes the carbocation. When we encountered a similar phenomenon in the chemistry of free radicals we noted that 3° radicals are roughly 30 kJ/mo) more 22 Organic Reaction Mechanism stable than I radicals.
Organic Name Reactions by K.R. Desai