Consider the reaction of each of the following with 1-bromopentane. Which one would have the highest

Consider the reaction of each of the following with 1-bromopentane. Which one would have the highest elimination/substitution ratio? A. NaOCH2CH3, ethanol, 55°C B. NaSH, ethanol-water, 25°C C. KOC(CH3)3, (CH3)3COH, 55°C

D. KCN, DMSO, 40°C

Solution:

We want to favor elimination over substitution. The substrate is 1-bromopentane which means it is primary ( bromine is attached to carbon which is attached to one carbon only). For a primary substrate, elimination, E2 is preferred is the reactant is a strong hindered base such as tertbutoxide, which is choice C.

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