Nucleophiles and Basicity - Online Tutor, Practice Problems & Exam Prep

Which nitrogen atom exhibits higher nucleophilicity between pyridine and piperidine? What factors contribute to its enhanced nucleophilicity?

Arrange the following anions in increasing order of their nucleophilic strength.

Which of the following would be a stronger nucleophile in DMSO?

• Cl⁻ or I⁻

Which of the following is the stronger nucleophile?

Which of the following nucleophiles would react more readily in an S _N2 reaction?

Which of the following amines would react more quickly as a nucleophile?

a. Which of the following species is a stronger nucleophile in water?

b. Which one is a stronger nucleophile in DMSO?

c. Which one is a stronger base?

• CH₃CH₂O⁻ or CH₃CH₂S⁻

Which of the following species is a better nucleophile?

a. CH₃O⁻ or CH₃NH⁻ in NH₃

b. CH₃O⁻ or CH₃NH⁻ in DMSO

Which of the following species is a stronger nucleophile in a polar protic solvent?

a. F⁻ or I⁻

b. F⁻ or Cl⁻

Arrange the members of each of the following groups from most nucleophilic to least nucleophilic in methanol.

a. NH₂⁻ and PH₂⁻

b. H₂O, H₂S, and H₂Se

What change would be observed in the ratio of substitution and elimination products of ethyl iodide in methanol if we change the nucleophile from HO⁻ to HS⁻?

Identify the stronger nucleophile in ethanol.

• CH₃CH₂O⁻ (ethanolate) or CH₃CH₂OH (ethanol)

Which of the following is the stronger nucleophile in ethanol?

• CH₃CH₂O⁻ (ethanolate) or CH₃CH₂OH (ethanol)

Arrange the following anions in decreasing order of their nucleophilicity in methanol.

Among the following pair of anions, identify the better nucleophile.

Show what will happen if the solvent behaves as a nucleophile rather than as a base in step 2 of an E1 reaction.

Using alcohol as the solvent, figure out which nucleophile in each pair is the stronger one in the S_N2 reaction and provide a brief explanation for your prediction.
(i) CH₃NH₂ or CH₃PH₂
(ii) CH₃O⁻ or H₂O

Using alcohol as the solvent, figure out which compound or ion in each pair is the stronger nucleophile in the S_N2 reaction. Explain your prediction.
(i) (CH₃CH₂)₃N or (CH₃CH₂)₂O
(ii) CH₃CH₂COO⁻ or CH₃CF₂COO⁻

The electrophilicity of carbonyls is demonstrated by its resonance form. What is the resonance form of the sulfonyloxonium ion? Why is the central X atom a great electrophile?

Which nucleophile would be more reactive?

Which of the following has a greater ratio of substitution-product-to-elimination-product?

In which solvent is the ethoxide ion expected to be a better nucleophile, dissolved in ethanol or dissolved in THF? Provide a brief explanation.

Determine which is the stronger between the given nucleophiles, using alcohol as the solvent, in the S_N2 reaction. Explain.

(i) CH₃CH₂CH(CH₃)O⁻ or CH₃CH₂CH₂CH₂O⁻

(ii) Br⁻ or F⁻

Using alcohol as a solvent, determine which is stronger between the given nucleophiles in the S_N2 reaction. Explain your prediction.

(i) (CH₃CH₂CH₂)₃N or (CH₃CH₃CH₂)₂NH

(ii) (CH₃CH₂)₂O or (CH₃CH₂)₂S

For the reaction:

Solvolysis of 2-chloro-2,3,3-trimethylpentane in ethanol

What is the function of solvent (ethanol) in E1 and S_N1 reactions?

Choose the better nucleophile between the two in the solvent given.

Which of the following species will have a higher ratio of S_N2 product compared to E2 product when it reacts with ethyl chloride in methanol: CH₃O⁻ or CH₃S⁻?