Daily answer writing · Tue, 20 Oct, 2026
Neopentyl bromide: why SN2 is very slow and solvolysis gives rearranged products
Neopentyl bromide, $\ce{(CH3)3C-CH2Br}$, is a primary alkyl halide, yet it reacts extremely slowly by the $S_N2$ mechanism. On solvolysis in aqueous ethanol it gives rearranged products such as 2-methylbut-2-ene and 2-methylbutan-2-ol. Explain with mechanisms.
Syllabus: Common to CSE Paper II, IFoS Paper II and Geo-Scientist Mains Paper III: nucleophilic substitution (SN1, SN2), carbocations, Wagner–Meerwein rearrangement.
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