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Ch. 18 - Ketones and Aldehydes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
Chapter 18, Problem 10a,b

Predict the products of the following reactions:
(a) Chemical reaction diagram showing a carbonyl compound with a chlorine atom, and reduction steps using LiAlH4 and H3O+.
(b) Chemical structure of a carbonyl compound with a chlorine atom, alongside a reducing agent, LiAlH(O-t-Bu)3.

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1
Step 1: Analyze the reactants and reagents in each reaction. In both cases, the starting material is benzoyl chloride (C6H5COCl), which contains a benzene ring attached to a carbonyl group and a chlorine atom. The reagents differ between the two reactions.
Step 2: For reaction (a), the reagents are (1) LiAlH4 and (2) H3O+. Lithium aluminum hydride (LiAlH4) is a strong reducing agent that reduces acyl chlorides to primary alcohols. The H3O+ step is used to protonate the intermediate formed during the reduction.
Step 3: For reaction (b), the reagent is LiAlH(O-t-Bu)3, which is a bulky reducing agent. This reagent selectively reduces acyl chlorides to aldehydes instead of further reducing them to alcohols due to steric hindrance from the bulky tert-butoxy groups.
Step 4: Predict the product for reaction (a). The acyl chloride (C6H5COCl) will be reduced by LiAlH4 to form benzyl alcohol (C6H5CH2OH) after protonation with H3O+.
Step 5: Predict the product for reaction (b). The acyl chloride (C6H5COCl) will be reduced by LiAlH(O-t-Bu)3 to form benzaldehyde (C6H5CHO) due to the selective reduction to an aldehyde.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Reaction Mechanisms

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