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Give the structure of the expected organic product in the reaction of 3−phenylpropanal with sodium hydroxide in ethanol at 70°C. If your structure contains an aldehyde do NOT use the condensed formula (−CHO), draw it out.

User Syltruong
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Answer:The expected product formed is 2-benzyl-5-phenylpent-2-enal .

Kindly refer the attachment for structure.

Step-by-step explanation:

3-phenylpropanal on reaction with sodium hydroxide undergoes an self- aldol condensation reaction and leads to formation of 2-benzyl-5-phenylpent-2-enal as final product.

In the first step of the reaction the highly basic hydroxide anions abstract a acidic hydrogen available at the carbon next to carbonyl carbon.These hydrogens are acidic because of the electron withdrawing effect of carbonyl group.

The proton abstraction leads to the generation of a carbanion and it further delocalizes forming an enolate anion.

The carbanion can behave as a nucleophile and can attack at the electrophilic carbon centers.

The carbonyl carbon is electrophilic in nature due to the electron withdrawl from oxygen which generates a partial positive charge on the carbonyl carbon.

The carbanion further reacts with another molecule of 3-phenylpropanal at its electrophilic carbonyl center and forms 2-benzyl-3-hydroxy-5-phenylpentanal. This reaction is known as self- aldol condensation reaction

2-benzyl-3-hydroxy-5-phenylpentanal has a OH group and this OH group is protonated through the available acidic protons from the solvent .

As OH is protonated it easily leaves leading to the formation of C=C double bond.

This reaction is one of the examples of Carbon-Carbon bond forming reaction.

Kindly refer attachments for reaction, structure and mechanism.

Give the structure of the expected organic product in the reaction of 3−phenylpropanal-example-1
User Swathy Krishnan
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