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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

What stereochemistry do you expect for the alkene obtained by E2 elimination of (1R, 2R)-1,2-dibromo-1,2-diphenylethane? Draw a Newman projection of the reacting conformation.

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?

(a)

Draw the structure and assign Z or E stereochemistry to the product you expect from E2 reaction of the following molecule with NaOH (green = Cl):

3-Bromo-1-butene and 1-bromo-2-butene undergoSN1 reaction at nearly the same rate, even though one is a secondary halide and the other is primary. Explain.

Predict the product(s) for each elimination reaction below. In each case show the mechanism. What do the mechanisms have in common? Why?

a.

b.

c.
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