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Leaving Group and Nucleophile Problems

Leaving Group and Nucleophile Problems

Leaving Group and Nucleophile Problems

Leaving Group and Nucleophile Problems

Leaving Group and Nucleophile Problems

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.