In each of the following indicate which reaction will occur faster. Explain your choice. A. BuBr...

In each of the following indicate which reaction will occur faster. Explain your choice.

A. BuBr or BuI with sodium cyanide in dimethyl sulfoxide (DMSO)
B. 1-Chloro-2-methylbutane or 1-chloropentane with sodium iodide in acetone
C. Hexyl chloride or cyclohexyl chloride with sodium azide in dimethyl formamide
D. Solvolysis of 1-bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol
E. Reaction of 1-chlorobutane with sodium acetate (NaOAc) in acetic acid or sodium methoxide in methanol
F.Reaction of 1-chlorobutane with sodium azide (NaN3) or sodium tosylate (NaOTs) in acetonitrile

Expert Solution

A) It is a SN2 reaction and Iodine is a better leaving group than Br so BuI react faster than BuBr.

B) it is a SN2 reaction and in 1-chloropentane has less sterically hindrance Alpha Hydrogen so easily attracks by the Nu- ion than 1-chloro-2-methylbutane so 1-Chloropentane react faster than 1-chloro-2-methylbutane.

C) Hexylchloride react with faster rate than cyclohexyl chloride because of in Hexylchloride less sterically hindrance Alpha Hydrogen than cyclohexyl chloride.

D) it is SN1 Reaction and tert.butyl Bromide produces more stable 3° Carbocation than in 1-bromo-2,2-dimethylpropane and more stable 3° carbocation give faster Reaction. Hence tert.butyl Bromide react with fater rate than 1-bromo-2,2-dimethylpropane.

E) sodium methoxide is stronger base it's give faster elemination reaction than other. Hence 1-chlorobutane react with fater rate in the presence of NaOCH3/HOCH3.

F) Faster Reaction in the presence of NaN3 because N3- ion stronger Nu- than -OTs ion

queen_honey_blossom answered 2 years ago

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