Which of the compounds below undergoes SN1 and E1 reactions in aqueous ethanol m

Question

Which of the compounds below undergoes SN1 and E1 reactions in aqueous ethanol most rapidly? a. cyclohexyl bromide b. methyl iodide c. 3-iodo-3-methylpentane d. isopropyl chloride e. 3-chloropentane Which of the following alkyl halides will undergo SN2 region most readily? a. 1-cholro-4-methylpentane b. 2-chloro-4-methylpentane c. 2-chloro-3-methylpentane d. 3-chloro-2-methylpantane e. 2-chloro-2-methylpentane The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise? a. SN1 b. SN2 c. E1 d. E2 e. none of the above Which of the following alkyl halides can produce only a single alkene product when reacting with KOH? a. 2-chloro-2-methyl pentane b. 3-chloro-3-ethyl pentane c. 3-chloro-2-methyl pentane d. 2-chloro-4-methyl pentane

Explanation / Answer

1) Tertiary carbon will undergo SN1 and E1 faster.

So 3-iodo-3-methylpentane(e)  will undergo SN1 and E1.

2) Primary carbon will undergo SN2 faster.

So 1-Chloro-4-methylpentane (a) wiil undergo SN2.

3) 2-Chloro-2-methylpentane undergo only SN1 and E1 since the carbon attached to chlorine is tertiary. Elimination only gives alkenes. So in order to give ether it should undergo SN1.

4) Only 3-Chloro 3-ethylpentane is symmetric alkane so it will only give symmetric alkene.

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