The mechanism for the given acid-catalyzed aldol reaction and the dehydration of the resulting aldol product has to be proposed. Concept Introduction: The nucleophilic addition of the enolate anion of one aldehyde or ketone to the carbonyl group of another aldehyde or ketone is known as Aldol reaction. The product of an Aldol reaction is β-hydroxyaldehyde or β-hydroxyketone. In acid-catalyzed Aldol reaction, acid is regenerated at the end of the reaction. The dehydration of the Aldol product (β-hydroxy aldehyde or ketone) occurs under acidic or basic conditions and form α,β-unsaturated aldehyde or ketone.

Question

R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…

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Question

Chapter 19, Problem 19.28P

Interpretation Introduction

Interpretation:

The mechanism for the given acid-catalyzed aldol reaction and the dehydration of the resulting aldol product has to be proposed.

Concept Introduction:

The nucleophilic addition of the enolate anion of one aldehyde or ketone to the carbonyl group of another aldehyde or ketone is known as Aldol reaction. The product of an Aldol reaction is β-hydroxyaldehyde or β-hydroxyketone. In acid-catalyzed Aldol reaction, acid is regenerated at the end of the reaction.

The dehydration of the Aldol product (β-hydroxy aldehyde or ketone) occurs under acidic or basic conditions and form α,β-unsaturated aldehyde or ketone.

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