Organic Chemistry
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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?
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?
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.
Which of the following is the stronger nucleophile in 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 SN2 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 SN2 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 SN2 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 SN2 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 SN1 reactions?
Choose the better nucleophile between the two in the solvent given.
Which of the following species will have a higher ratio of SN2 product compared to E2 product when it reacts with ethyl chloride in methanol: CH3O− or CH3S−?