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–
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8. Elimination Reactions
Nucleophiles and Basicity
Multiple Choice
Which of the following species is the least nucleophilic?
A
B
C
D
Verified step by step guidance1
Understand that nucleophilicity refers to the ability of a species to donate a pair of electrons to an electrophile, often influenced by charge, electronegativity, solvent effects, and steric hindrance.
Compare the given species: hydroxide ion (OH\(\textsuperscript{-}\)), methyl anion (CH\(\textsubscript{3}\[\textsuperscript{-}\)), water (H\(\textsubscript{2}\)O), and amide ion (NH\(\textsubscript{2}\]\textsuperscript{-}\)). Note their charges and electron density availability.
Recognize that negatively charged species (OH\(\textsuperscript{-}\), CH\(\textsubscript{3}\[\textsuperscript{-}\), NH\(\textsubscript{2}\]\textsuperscript{-}\)) generally have higher nucleophilicity than neutral species like H\(\textsubscript{2}\)O because the negative charge increases electron density and reactivity.
Consider that among the negatively charged species, factors like electronegativity and resonance can affect nucleophilicity, but since water is neutral and has lone pairs less available for donation, it is expected to be the least nucleophilic.
Conclude that water (H\(\textsubscript{2}\)O) is the least nucleophilic species among the options because it is neutral and its lone pairs are held more tightly compared to the negatively charged ions.
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