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Chapter 6: 6-22P (page 312)

Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.

Short Answer

Expert verified

Solvolysis is a type of substitution reaction in which solvent molecules act as nucleophiles.

Step by step solution

01

Step1: Definition of solvolysis

Solvolysis is a type of substitution reaction in which solvent molecules act as nucleophiles.

02

Step2: In SN1 mechanism reaction take place in two steps,

The first step is the formation of carbocation.

Second step is an attack of nucleophile on carbocation to give the final product.

03

Step3:

Here in above reaction first step is formation of carbocation take place with the removal of bromide ion. Since reaction take place in ethanol, in second step attack of ethanol on carbocation take place followed by removal of hydrogen results in final product.

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Most popular questions from this chapter

Draw the structures of the following compounds.

(a)sec-butyl bromide

(b)isobutyl chloride

(c) 1,2-chloro-3-methylpentane

(d) 2,2,2-tribromoethanol

(e) trans-1-bromo-2-methylcyclohexane

(f) methylene bromide

(g) iodoform

(h) 1-bromo-1-isopropylcyclopentane

(i) tert-pentyl bromide

Give the structures of the following compounds.

(a) Methylene chloride

(b) Carbon tetrachloride

(c) 3-iodo-2-methylpentane

(d) Chloroform

(e) 2-chloro-3-ethyl-2-methyhexane

(f) Isobutyl iodide

(g) Cis-1-chloro-3-(chloromethyl)cyclohexane

(h) Tert-butyl bromide

Predict the major product of the following substitutions.

Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered ring compounds. Show how these three pesticides are composed of two five-membered rings.

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

(a) ethyl chloride or ethyl iodide

(b) 1-bromopropane or cyclopropane

(c) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene

(d) cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane.
See all solutions

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