Question

Draw the aldol product formed from each compound.

   Draw the aldol product formed from each compound.

Organic Chemistry

Organic Chemistry

Janice Gorzynski… 4th Edition

Chapter 24, Problem 1

Instant Answer

Solved by Expert Ian Kaigh

12/30/2019

Step 1

Discovered independently by the Russian chemist Alexander Borodin in 1869 and by the French chemist Charles-Adolphe Wurtz in 1872, the reaction combines two carbonyl compounds (the original experiments used aldehydes) to form a new β-hydroxy carbonyl compound. Show more…

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Draw the aldol product formed from each compound.

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Key Concepts

Carbonyl Electrophilicity

Carbonyl groups are polarized due to the electronegativity difference between carbon and oxygen, rendering the carbon atom electrophilic. This electrophilicity makes the carbonyl carbon susceptible to nucleophilic attack by the enolate ion formed in the reaction. Recognizing the electrophilic character of the carbonyl is essential for predicting the site of attack in the aldol reaction.

Aldol Condensation

In many cases, the initial aldol addition product undergoes dehydration to yield a conjugated enone system in a process known as aldol condensation. This dehydration step is typically catalyzed by acid or base and results in the formation of an ?,?-unsaturated carbonyl compound through the loss of water. The condensation product often exhibits increased stability due to conjugation.

Aldol Reaction Mechanism

This is a fundamental reaction in organic chemistry where an enolate ion, formed from the deprotonation of a carbonyl compound at the alpha position, adds to the electrophilic carbonyl carbon of another molecule. The reaction generally results in the formation of a ?-hydroxy carbonyl compound, known as the aldol addition product. This mechanism underpins many synthetic strategies by coupling two carbonyl-containing fragments together.

Enolate Ion Formation

A key step in the aldol reaction is the formation of the enolate ion. Under basic conditions, an alpha hydrogen is removed from a carbonyl compound to form a resonance-stabilized enolate. This enolate serves as the nucleophile in the subsequent addition step, attacking a second carbonyl compound. The stability and reactivity of enolates are central to understanding the aldol reaction.

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