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Chapter 11: 46aE (page 350)

Which reaction in each of the following pairs would you expect to be faster?

(a) TheSN2displacement byI-鈥�on鈥�CH3Cl鈥�or鈥�CH3OTs

Short Answer

Expert verified

CH3OTs鈥�shows鈥�fast鈥�reaction鈥�thanCH3Cl鈥�

Step by step solution

01

SN2reaction

It is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed both processes occur simultaneously. Hence, it鈥檚 a single-step reaction.

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 that are ready for bonding.

03

Species react faster I-

If the species areis a better leaving group then it reacts faster with the nucleophileCH3OTs

is a better leaving group than CH3Cl鈥�

CH3OTsis鈥嬧赌�show鈥�fast鈥�reaction鈥�than鈥�CH3Cl鈥�

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Most popular questions from this chapter

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Propose a structure for an alkyl halide that gives only (E)-3-methyl-2-phenyl-2-pentene on E2elimination. Make sure you indicate the stereochemistry.

What product would you expect from SN2reaction of 1-bromobutane with each of the following?

(a)NaI (b) KOH (c)H鈥�C鈮�C鈥�Li(d)NH3

Which substance in each of the following pairs is more reactive as a nucleophile? Explain.

(a)CH32N-orCH32NH(b) (CH3)3Bor(CH3)3N(c)H2OorH2S

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.

.
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