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8. Elimination Reactions

Nucleophiles and Basicity

8. Elimination Reactions

Nucleophiles and Basicity

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Understanding the difference between basicity and nucleophilicity.

Understanding the difference between basicity and nucleophilicity.

Johnny Betancourt

Practice this topic

Textbook Question

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent). Explain your prediction. e. (CH3)3N or (CH3)2O f. CH3COO- or CF3COO-

Textbook Question

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent). Explain your prediction. c. NH3 or PH3 d. CH3S- or H2S

Textbook Question

[FIGURE: KEY MECHANISM 7-1]

Show what happens in step 2 of the example if the solvent acts as a nucleophile (forming a bond to carbon) rather than as a base (removing a proton).

Textbook Question

a. Which is a stronger base: RO− or RS−? b. Which is a better nucleophile in an aqueous solution? c. Which is a better nucleophile in DMSO?

Textbook Question

Which is a better nucleophile? e. HO− or -NH2 in NH3 f. HO− or -NH2 in DMSO

Textbook Question

Which member of each pair is a better nucleophile in methanol? e. I− or Br− f. Cl− or Br−

Textbook Question

Rank the following species in each set from best nucleophile to poorest nucleophile. c. H2O and NH3 in methanol d. Br−, Cl−, I− in methanol

Textbook Question

How does the ratio of substitution product to elimination product formed from the reaction of propyl bromide with CH3O− in methanol change if the nucleophile is changed to CH3S−?

Textbook Question

Which is a better nucleophile? c. CH3O− or CH3OH in CH3OH

Textbook Question

Which is a better nucleophile? d. CH3O− or CH3OH in DMSO

Textbook Question

Rank the following species in each set from best nucleophile to poorest nucleophile. a.

Textbook Question

Rank the following species in each set from best nucleophile to poorest nucleophile. b.

Textbook Question

Rank the reactivity of the following anions with a general electrophile from least to most reactive.

Textbook Question

Which nucleophile would be more reactive in the solvent given? (a) vs.

Textbook Question

Which nucleophile would be more reactive in the solvent given? (b) vs.

Textbook Question

For each pair, choose the more reactive nucleophile. (a) vs.

Textbook Question

(•) For each pair, choose the nucleophile that would react most quickly in an Sₙ2 reaction (assume H₂O is the solvent). (a) vs.

Textbook Question

(•) For each pair, choose the nucleophile that would react most quickly in an Sₙ2 reaction (assume H₂O is the solvent). (b) vs.

Textbook Question

(•) For each pair, choose the nucleophile that would react most quickly in an Sₙ2 reaction (assume H₂O is the solvent). (d) vs.

Textbook Question

In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?

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Textbook Question

Between pyrrole and pyrrolidine, which nitrogen would be most nucleophilic? Why? vs.

Textbook Question

The zwitterionic form of carbonyls is often used to explain their electrophilicity. Draw the zwitterionic structure of NO⁺₂. Why is this such a great electrophile at the central nitrogen?

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Textbook Question

Would you expect the following bases to favor E1 or E2 elimination?

(c) <IMAGE>

Textbook Question

For each pair, choose the more reactive nucleophile.

(b) <IMAGE> vs. <IMAGE>

Textbook Question

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

Textbook Question

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

Textbook Question

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent).

Explain your prediction.

a. (CH3CH2)3N or (CH3CH2)2NH

b. (CH3)2O or (CH3)2S

Textbook Question

For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol as the solvent).

Explain your prediction.

g. (CH3)2CHO- or CH3CH2CH2O-

h. I- or Cl-

Textbook Question

SN1 substitution and E1 elimination frequently compete in the same reaction.

Compare the function of the solvent (methanol) in the E1 and SN1 reactions.

Textbook Question

Which nucleophile would be more reactive in the solvent given?

(c) <IMAGE> vs. <IMAGE>

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