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Leaving Group and Nucleophile Problems

Problem : Rank the leaving groups attached to the "R" in order of increasing nucleophilicity.

R-OEt < R-Br < R-OH2 +    

Water is extremely stable, and thus -OH2 + is a great leaving group. Br- is less basic and more stable than EtO- . Thus -Br is a better leaving group than -OEt .

Problem : Identify the α -carbon, β -carbon(s), and β -hydrogens in the following molecule.

The molecule does not have β -hydrogens.

Problem : Is ethoxide a better nucleophile in methanol or acetone?

Methanol is a polar, protic solvent. Acetone is polar and aprotic. Ethoxide ions in acetone will be more nucleophilic than ethoxide in methanol.