Consider the following table of standard electrode potentials for a series of hypothetical reactions in aqueous solution:
(a) Which substance is the strongest oxidizing agent? Which is weakest?
(b) Which substance is the strongest reducing agent? Which is weakest?
(c) Which substance(s) can oxidize \(\mathrm{C}^{2+}\)? [Sections 20.4 and 20.5]
Text Transcription:
{C}^{2+}
Chapter 23 and 24 General Ketone with Base reaction Malonic ester synthesis ● Decarboxylation = loss of CO2 ● Carboxylic acid with 1 or 2 carbon chains attached to the α carbon Acetoacetic ester synthesis ● Methyl ketone with 1 or 2 R groups attached to the other α carbon Mechanism Acetoacetic ester synthesis How to Make Chapter 24 ● Enolate reacts with carbonyl compound Aldol Reaction ● 2 aldehydes or ketones react product is a β- hydroxy carbonyl Mechanism of aldol ● 2 Aldehydes = Aldol products favored ● 2 Ketones = Aldol starting materials favored ● β – hydroxyl carbonyl compounds can undergo base-catalyzed dehydration ● All alcohols undergo acid- catalyzed dehydration Mechanism ● This is likely to happen with conjugated molecules Aldol reaction ● Enolate (nucleophile) + aldehyde or ketone in base ● Product is β- hydroxyl carbonyl Crossed Aldol reaction ● Two different carbonyl compounds reacting ● ● Better results if only one compound has α-H’s or it's much more acidic ● Better if one is much more electrophilic Directed Aldol ● Selectively deprotonate 1 compound at low temperature with LDA ● Then add second compound 1:1 of Ketone: LDA ~100% of enolate formed Dicarbonyl compounds can do intramolecular aldol
