Textbook Question
Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et2O is diethyl ether.)
a.
b.
c.
3
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7. Substitution Reactions
Good Leaving Groups
Multiple Choice
Which of the following is a good nucleophile and a strong base?
A
(nitrate ion)
B
(hydroxide ion)
C
(chloride ion)
D
(hydride ion)
Verified step by step guidance1
Understand the definitions: A good nucleophile is a species that donates an electron pair to an electrophile, and a strong base is a species that readily accepts a proton (H+). While nucleophilicity and basicity are related, they are not always the same; some ions can be strong bases but poor nucleophiles, and vice versa.
Analyze each ion given in the problem: Nitrate ion (NO\_3\^-), hydroxide ion (O\^-), chloride ion (Cl\^-), and hydride ion (H\^-). Consider their charge, electronegativity, and resonance stabilization to assess nucleophilicity and basicity.
Nitrate ion (NO\_3\^-) is resonance stabilized, which delocalizes its negative charge, making it a weak base and poor nucleophile.
Hydroxide ion (O\^-) has a localized negative charge on oxygen, making it both a strong base and a good nucleophile due to its high electron density and lack of resonance stabilization.
Chloride ion (Cl\^-) is a weaker base compared to hydroxide but can be a decent nucleophile; hydride ion (H\^-) is a very strong base but a poor nucleophile in typical organic reactions due to its high reactivity and instability.
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