Can carboxylic acids do aldol reaction?

They do, if you beat them to it: Dissolve the carboxylic acid in a polar, aprotic solvent, such as 1,2-dimethoxyethane, 1,4-dioxane, tetrahydrofuran, etc.

What is needed for an aldol reaction?

‘Aldol’ is an abbreviation of aldehyde and alcohol. When the enolate of an aldehyde or a ketone reacts at the α-carbon with the carbonyl of another molecule under basic or acidic conditions to obtain β-hydroxy aldehyde or ketone, this reaction is called Aldol Reaction.

Can acetic acid undergo aldol condensation?

In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. Independently synthesized TMSOAc also undergoes aldol additions under similar conditions.

Which compound give aldol reaction?

In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or “aldol” (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals….

Do Enolates react with carboxylic acid?

Esters contain acidic α protons which can be removed with a strong base to form enolate ions.

Can carboxylic acids form Enolates?

Ketones, carboxylic esters, carboxylic acids, and carboxamides can in general be converted to enolates by deprotonation with strong bases like lithium diisopropylamide. The enolates can also be formed by conjugate reduction reactions.

What are practical uses of the aldol reaction?

The reaction is commonly used to produce solvents such as alcohol isophorone and diacetone. It works as an intermediate for perfume production. It is also used in pharmaceutical manufacturing, unsaturated ketones and chalcones known as aromatic ketones. Usually, it is used to create plasticizers as well.

Which of the following carbonyl compound undergoes the aldol condensation reaction?

All carbonyl compounds containing α−H or α−D undergo aldol condensation. In given example, benzaldehyde does not contain α−H to -CHO, hence does not undergo aldol condensation.

Are carboxylic acids Enolizable?

An enolizable ester is a carboxylic acid ester whose molecule has one or more alpha hydrogens.

What are the reactions of carboxylic acid derivatives?

These reactions, which included halogenation, isotope exchange and the aldol reaction, take place by way of enol tautomer or enolate anion intermediates, a characteristic that requires at least one hydrogen on the α-carbon atom. In this section similar reactions of carboxylic acid derivatives will be examined.

Do carboxylic acids need to be activated for Alpha-halogenation?

Carboxylic acids that have a higher equilibrium enol concentration do not need to be activated for alpha-halogenation to occur, as demonstrated by the substituted malonic acid compound in the second equation below. The enol concentration of malonic acid (about 0.01\%) is roughly ten thousand times greater than that of acetic acid.

How is acyl chloride converted to carboxylic acid?

Thus, conversion of the acid to its acyl chloride derivative is followed by alpha-bromination or chlorination, and the resulting halogenated acyl chloride is then hydrolyzed to the carboxylic acid product.

How do aldehydes and ketones undergo electrophilic substitution at alpha carbon?

Many aldehydes and ketones were found to undergo electrophilic substitution at an alpha carbon. These reactions, which included halogenation, isotope exchange and the aldol reaction, take place by way of enol tautomer or enolate anion intermediates, a characteristic that requires at least one hydrogen on the α-carbon atom.