Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d)

Verified step by step guidance

1. Identify the functional group in the given compound. The structure shows a six-membered cyclic ketone (cyclohexanone) with a carbonyl group (C=O).
2. Understand the role of LiAlH4 (Lithium Aluminum Hydride). It is a strong reducing agent that reduces ketones to secondary alcohols by adding hydrogens to the carbonyl group.
3. Write the mechanism of the reaction. LiAlH4 donates a hydride ion (H⁻) to the carbonyl carbon, breaking the double bond and forming an alkoxide intermediate.
4. Perform hydrolysis. The alkoxide intermediate reacts with water during the hydrolysis step to form the final alcohol product.
5. Predict the product. The ketone (cyclohexanone) is reduced to a secondary alcohol (cyclohexanol) with the hydroxyl group (-OH) replacing the carbonyl group.

Key Concepts

Lithium Aluminum Hydride (LiAlH4) Reactivity

LiAlH4 is a strong reducing agent commonly used in organic chemistry to reduce carbonyl compounds, such as aldehydes and ketones, to their corresponding alcohols. It can also reduce esters and carboxylic acids, making it a versatile reagent in organic synthesis. Understanding its reactivity is crucial for predicting the products of reactions involving carbonyl-containing compounds.

Hydrolysis of Alkoxides

After the reduction of a carbonyl compound by LiAlH4, the resulting alkoxide intermediate can be hydrolyzed by adding water or an alcohol, such as methanol. This hydrolysis step converts the alkoxide into an alcohol, which is the final product of the reaction. Recognizing the role of hydrolysis is essential for determining the final products in reduction reactions.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves as both a solvent and a reactant during hydrolysis. Understanding how solvents interact with reactants and products helps predict reaction mechanisms and product distributions, which is vital for accurately forecasting the results of the given reaction.