Final answer:
The expected product of an aldol condensation of phenylacetaldehyde without dehydration is a β-hydroxyaldehyde, specifically formed through nucleophilic addition of an enolate anion to another aldehyde molecule.
Step-by-step explanation:
The expected product for the aldol condensation of phenylacetaldehyde without dehydration is called an aldol product. The reaction proceeds through a nucleophilic addition of one aldehyde molecule to another, forming a β-hydroxyaldehyde.
To illustrate the reaction, two molecules of phenylacetaldehyde will be involved. The first step is the formation of an enolate anion from one molecule of phenylacetaldehyde. This occurs by the removal of the alpha hydrogen (adjacent to the carbonyl group) by a base. The enolate anion then acts as a nucleophile and attacks the carbonyl carbon of a second molecule of phenylacetaldehyde. This results in the formation of the aldol addition product, which is still a β-hydroxyaldehyde because we are not dehydrating the product in this scenario.
The expected structure of the non-dehydrated aldol product from phenylacetaldehyde will have the following features: a phenyl ring, an aldehyde group (from the second phenylacetaldehyde molecule that did not form the enolate), and a hydroxyl group (β-hydroxy) next to the newly formed secondary alcohol carbon (which was the nucleophilic carbon of the enolate). Essentially, this aldol product will be a β-hydroxyaldehyde with a phenyl group attached to the β-carbon.
Since the question specifies not to worry about stereochemistry, we won't discuss potential isomers. Also, without dehydration, the β-hydroxyaldehyde formed is the final product, and no further elimination to form an α,β-unsaturated aldehyde will take place. Therefore, the product retains its hydroxyl group.