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Amongst the following pairs, predict which one would be the best nucleophile in a solution of...

Amongst the following pairs, predict which one would be the best nucleophile in a solution of ethanol. Justify your answer.

a). CH3CH2OH vs CH3CH2ONa

b) Br - vs I -

c) F3C-CH2-C(=O)-ONa vs H3C-C(=O)-ONa

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Answer #1

a) CH3CH2OH is the best nucleophile, whereas CH3CH2ONa will acts as a base.

b) I- is the best nucleophile compared to the Br- (in polar protic solvent such as ethanol, hydrogen bonding has a dramatic effect on nucleophilicity. In hydrogen bonding solvents (polar protic solvents) the most basic nucleophiles (e.g. Br-) are surrounded by an entourage of solvent molecules will decreases nucleophilicity).

c) F3C-CH2-C(=O)-ONa is the best nucleophile compared to H3C-C(=O)-ONa.

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