Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.
(f) zinc amalgam and dilute hydrochloric acid

Verified step by step guidance

1. Identify the functional group in cyclohexanecarbaldehyde. The molecule contains an aldehyde group (-CHO) attached to a cyclohexane ring.
2. Understand the role of zinc amalgam and dilute hydrochloric acid. This combination is used in the Clemmensen reduction, which reduces aldehydes and ketones to their corresponding alkanes.
3. In the Clemmensen reduction, the aldehyde group (-CHO) is reduced to a -CH3 group. This involves the removal of the oxygen atom from the aldehyde and the addition of two hydrogen atoms.
4. Write the reaction mechanism conceptually: The aldehyde group undergoes reduction in the presence of zinc amalgam and HCl, resulting in the formation of cyclohexane with a methyl group attached (cyclohexylmethane).
5. Verify the product structure: The aldehyde group is completely reduced, and no other functional groups are present in the molecule. The final product is cyclohexylmethane.

Key Concepts

Wurtz Reaction

The Wurtz reaction involves the reduction of carbonyl compounds using zinc amalgam in the presence of an acid. In this context, cyclohexanecarbaldehyde is reduced to form cyclohexylmethanol. This reaction is significant in organic synthesis for converting aldehydes and ketones into alcohols.

Reduction Reactions

Reduction reactions in organic chemistry refer to the gain of electrons or decrease in oxidation state by a molecule. In the case of cyclohexanecarbaldehyde, the carbonyl group (C=O) is reduced to a hydroxyl group (C-OH), resulting in the formation of an alcohol. Understanding reduction mechanisms is crucial for predicting product formation.

Aldehyde Reactivity

Aldehydes are highly reactive due to the presence of the carbonyl group, which is polarized and susceptible to nucleophilic attack. In the reaction with zinc amalgam and dilute hydrochloric acid, the aldehyde undergoes reduction, highlighting its reactivity compared to other functional groups. Recognizing the behavior of aldehydes is essential for predicting reaction outcomes.