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Chapter 9: Q58P (page 442)

Would you expect acetate ion (CH3CO2-) to be a better nucleophile in an SN2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?

Short Answer

Expert verified

Yes,acetate ion (CH3CO2-) to be a better nucleophile in an SN2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide.

Step by step solution

01

Explanation

Acetate ion will be a better nucleophile in dimethyl sulfoxide because dimethyl sulfoxide will not stabilize the negatively charged nucleophile by ion-dipole interactions, whereas methanol will stablize it by ion-dipole interactions

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Most popular questions from this chapter

Which member of each pair is a better nucleophile in methanol?

a. H2O or HO-

b. NH3 or H2O

c. H2O or H2S

d. HO- or HS-

e. I- or Br-

f. Cl-or Br-

A chemist wanted to synthesize the aesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:

a. trans-1-chloro-2-methylcyclohexane + CH3O-

b. cis-1-chloro-2-methylcyclohexane + CH3O鈭�

c. 1-chloro-1-methylcyclohexane + CH3O-

d. 1-chloro-1-methylcyclohexane + CH3OH

When the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation of these products.

What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with the hydroxide ion?
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