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Chapter 9: Q79P (page 452)

Would you expect methoxide ion to be a better nucleophile if it is dissolved in CH3OH or if it is dissolved in DMSO? Why?

Short Answer

Expert verified

Methoxide ion is better nucleophile in DMSO, because DMSO cannot stabilize the anion by hydrogen bonding.

Step by step solution

01

Structure of DMSO

As in this delocalization occurs so it is most stable compound so methoxide ion is not a better nucleophile if we dissolved in DMSO.

CH3OH can form hydrogen bonding with methoxide ion.

02

Final answer

Methoxide ion is better nucleophile in DMSO, because DMSO cannot stabilize the anion by hydrogen bonding.

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Most popular questions from this chapter

How will the rate of the reaction between bromomethane and hydroxide ion be affected if the following changes in concentration are made?

a. The concentration of the alkyl halide is not changed and the concentration of the nucleophile is tripled.

b. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is not changed.

c. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is doubled.

What percentage of the reaction described in Problem 31 takes place by the E2 pathway when [HO-] = 0.0025 M?

The reaction of chloromethane with hydroxide ion at 30°C has a ΔG° value of -21.7 kcal/mol. What is the equilibrium constant for the reaction?

Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?

Explain why only a substitution product and no elimination product is obtained when the following Compound reacts with sodium methoxide:
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