What is the aldol addition product formed from the reaction of acetone, (ch3)2co, with itself?

In this reaction First Acetone is treated with Base, the base abstracts the mildly acidic proton present at alpha position to carbonyl group. The resulting specie called enolate act as a nucleophile and attacks on second Acetone molecule which upon acid treatment yields the Aldol Product (4-hydroxy-4-methylpentan-2-one). While, aldol upon dehydration yield Chalcone (4-methylpent-3-en-2-one). The Reaction is as follow,

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AkshayG AkshayG · Answer 2 · 2019-11-12T10:14:37+01:00

The aldol addition product of two molecules of acetone will give [tex]\boxed{{\text{4 - methylpent - 3 - en - 2 - one}}}[/tex]. .(Refer to the attached image).

Further explanation:

Aldol reaction is a reaction where enolate of an aldehyde or ketone reacts with of another carbonyl compound in an acidic and basic condition to produce . The contains which is highly acidic in nature due to polar carbonyl group adjacent to it and also the enolate ion formed by the abstraction of hydrogen is resonance stabilized.

In an aldol condensation reaction, [tex]{\beta -{\text{ hydroxy}}[/tex] aldehyde or ketone undergoes further dehydration to produce an [tex]{\alpha ,\beta - {\text{unsaturated}}\;{\text{aldehyde}}\;{\text{or}}\;{\text{ketone}}[/tex]. Aldol is an abbreviation formed for the reaction as the product of reaction yields a compound containing aldehyde and alcohol. This reaction is a nucleophilic addition reaction.

Mechanism of the reaction between two acetone molecules in the basic medium is as follows:

Step 1: Formation of enolate ion of an acetone molecule:

Hydroxide ion abstracts a [tex]{\alpha -{\text{hydrogen }}[/tex] present on [tex]{\alpha - {\text{Carbon}}[/tex] which leads to the formation of enolate ion.

Step 2: Formation of alkoxide ion of an acetone molecule:

The enolate ion adds to another acetone molecule by attacking the carbonyl carbon of it.

Step 3: Formation of [tex]{\mathbf{\beta - hydroxy}}[/tex] aldehyde or ketone (aldol):

Alkoxide ion is protonated by water molecule to form [tex]{\beta - {\text{hydroxy}}\;{\text{ketone}}[/tex] (aldol) which exists in equilibrium with enolate form in basic condition.

Step 4: Dehydration for the formation of [tex]{\mathbf{\alpha ,\beta - unsaturated}}\;{\mathbf{ketone}}[/tex].

[tex]{\beta - {\text{hydroxy}}\;{\text{ketone}}[/tex] loses a water molecule to form [tex]{\alpha ,\beta - {\text{unsaturated}}\;{\text{ketone}}[/tex].

The aldol addition product of two molecules of acetone is [tex]{\mathbf{4 - methylpent - 3 - en - 2 - one}}[/tex] .

Learn more:

1. Determination of heat of vaporization of benzaldehyde: https://brainly.com/question/7599651

2. Why extraction is useful as the pre-purification method for organic compounds: https://brainly.com/question/5881840

Answer details:

Grade: High school

Subject: Chemistry

Chapter: Carbonyl Compounds

Keywords: aldol condensation, 4-methylpent-3-en-2-one, ketones, addition product, alpha hydrogen, acidity, resonance, and alpha beta-unsaturated carbonyl compounds.