Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

The major product in the above reaction is

Options:

\(C_6H_5CH=CHC_6H_5\)

\(C_6H_5CH=CHCOC_6H_5\)

\(C_6H_5CH_2OH + C_6H_5CH(OH)C_6H_5\)

\(C_6H_5CH_2OH + C_6H_5COONa\)

Correct Answer:

\(C_6H_5CH=CHCOC_6H_5\)

Explanation:

The correct answer is option 2. \(C_6H_5CH=CHCOC_6H_5\).

The given reaction is Cross Aldol condensation.

The condensation reaction between two different molecules of an aldehyde or ketone in a protic solvent such as water or alcohol constitutes the crossed aldol reaction. When condensation is between two different carbonyl compounds, it is called crossed aldol condensation. When both aldehydes have alpha hydrogens, both can form carbanions and can also act as carbanion acceptors. Hence a mixture of four products is formed which has little synthetic value.

If one of the aldehydes has no alpha hydrogen then it can act only as a carbanion acceptor. In such a case, only two products are formed. A common substrate for the crossed aldol reaction is an aromatic aldehyde, which has no alpha position. Furthermore, dehydration of the initial condensation product is rapid which leads to the formation of the α, β – unsaturated ketone and prevents the retro-aldol reaction from taking place.

Mechanism :