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Chapter 11: Q 11-11-41 E-b (page 350)

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(b) CH3CH2Iin ethanol or dimethyl sulfoxide

Short Answer

Expert verified

CH3CH2I

Step by step solution

01

SN2 reaction

An old bond is broken and a new bond is formed in this nucleophilic substitution reaction. This occurs simultaneously. The reaction is therefore single-step.

The two reacting species are involved in the rate determining steps.

02

Nucleophile

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons ready for bonding.

03

Species react faster with OH-

If the species is a better leaving group, it reacts faster with the nucleophile.

I am a better leaving group than dimethyl sulfoxide (DMSO) in ethanol, aprotic solvent, and form hydrogen bonds with hydroxide. It decreases the reactivity of the reaction.

CH3CH2I shows fast reaction than DMSO

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Most popular questions from this chapter

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.

.

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(d) NaCN

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

(b) CH3CO2-

Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB or E2:

a)

What product would you expect to obtain from SN2 reaction of OH-with (R)-2-bromobutane? Show the stereochemistry of both the reactant and product.
See all solutions

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