Explain why when a solution of (S)-3-phenyl-2-butanone in aqueous ethanol is treated with acids or bases it gradually loses its optical activity. (b) Why does the racemization of the compound from the previous section in an acid medium occur at the same speed as the halogenation in an acid medium? (c) Why does the iodination of said compound in an acid medium occur at the same rate as acid-catalyzed bromination?

Treating cis -2-propyl-3-methyl-cyclopentanone with a weak base transforms it into its trans stereoisomer. Reason this phenomenon and draw the corresponding structures.

Write the structure of all the possible enolates of each ketone or aldehyde. Indicate which would be the most favored under kinetic or thermodynamic control. Explain.


Which of the following compounds would test positive for iodoform?: (a) Acetone; (b) Acetophenone; (c) Pentanal; (d) 1-Butanol; (e) 2-Pentanone; (f) 3-Pentanone.

Indicate the products (if any) with deuterium incorporation that are formed when treating the following compounds with D 2 O/NaOD.

(a). Cyclohexanone; (b) 2,2-Dimethylpropanal; (c) 3,3-Dimethyl-2-butanone; (d) statement

Draw the products of acid- and base-catalyzed bromination of acetylcyclopentane. Indicate the major product. Reason your answer.

Explain the fact that cyclohexanone enolate reacts with 2-bromobutane giving rise to two reaction products, while only one is formed with 2-bromo-2-methylpropane.

alkylation-intramolecular-statement Reaction of the indicated compound with base provides three isomeric C 8 H 12 O products resulting from intramolecular alkylations. Indicate what they are.

The alkylation of the enolate of ketone A is very difficult to stop before the dialkylation occurs, as indicated below. Show how the monoalkylated ketone B could be obtained.