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Any compound or ion with at least one lone pair can be considered a base and/or

ID: 937490 • Letter: A

Question

Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp3-carbon atoms.

Please show an example of a) a species that is a strong nucleophile and a strong base, b) a species that is a weak nucleophile and a weak base.

c) a species that is a weak nucleophile and a strong base, d) a species that is a strong nucleophile and a weak base,

Explanation / Answer

1) a species that is a strong nucleophile and a strong base is LiCH3

2) a species that is a weak nucleophile and a weak base is H2O

3) a species that is a weak nucleophile and a strong base is t-BuLi

4) a species that is a strong nucleophile and a weak base is NH3

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