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Rank the relative nucleophilicity of the indicated species in ethanol.

CH3COOH

CH3OH

CH3COO-

CH3S-

CH3O-

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The more basic the substance is then it will also be a stronger nucleophile. We can first eliminate the substances that are not negatively charged. This is because nucleophiles are substances that are more negatively charged or are likely to form bonds with other species to become neutral. Then we are left with CH3OO-, CH3S- and CH3O-. Off the bat we can conclude that CH3OO- is not the strongest nucleophile because there is a extra oxygen that serves as a electron withdrawing group that makes the substance more stable. Afterwards we have to look at whether sulfur or oxygen will be more reactive. Oxygen is a more electronegative atom which means that it will be less likely to react since it tends to hold onto electrons more tightly than sulfur. Therefore CH3S- would be the strongest nucleophile. The order will go from strongest to weakest: as CH3S-, CH3O-, CH3OO-, CH3OH, CH3COOH

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