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Which of the following sets contains only species that can act as nucleophiles?

1. Cl(-), OH(-), R(-) (carbanion),:CH2 (carbene)
2. CH3-C(=O)-O(-) (acetate), N3(-) (azide), H3O(+), SH(-)
3. CH2=CH2, CH3-NH2, CH3-CH2-OH, benzene
4. H(-) (hydride),:CN(-) (cyanide), CS2, toluene

Correct answer: CH2=CH2, CH3-NH2, CH3-CH2-OH, benzene

Solution

Set 2 contains H3O(+), a cation/electrophile, so it is not an all-nucleophile set. Set 1 includes:CH2 (carbene), which is electrophilic. Set 4 includes CS2 and toluene which are weak, and the inclusion of typical electrophilic considerations rules them out. Set 3 (ethene with pi electrons, methylamine with N lone pair, ethanol with O lone pair, benzene with aromatic pi cloud) are all electron-rich nucleophiles.

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