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Ch. 18 - Ketones and Aldehydes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 18, Problema 50a

Propose mechanisms for the following reactions.
(a) Chemical reaction diagram showing nucleophilic addition of methanol to an aldehyde, forming an acetal.

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Step 1: Identify the starting material and the product. The starting material is benzaldehyde (Ph-CHO), and the product is an acetal (Ph-CH(OCH3)2). This reaction involves the conversion of an aldehyde into an acetal in the presence of methanol (CH3OH) and an acid catalyst (H+).
Step 2: Protonation of the carbonyl oxygen. The acid catalyst (H+) protonates the oxygen atom of the aldehyde group, increasing the electrophilicity of the carbonyl carbon and making it more susceptible to nucleophilic attack.
Step 3: Nucleophilic attack by methanol. Methanol (CH3OH) acts as a nucleophile and attacks the carbonyl carbon, forming a tetrahedral intermediate. This intermediate has a hydroxyl group (-OH) and a methoxy group (-OCH3) attached to the carbon.
Step 4: Formation of the hemiacetal. The intermediate undergoes deprotonation at the hydroxyl group, resulting in the formation of a hemiacetal (Ph-CH(OH)(OCH3)).
Step 5: Conversion to acetal. The hydroxyl group of the hemiacetal is protonated again by the acid catalyst, making it a good leaving group. A second molecule of methanol attacks the carbon, replacing the hydroxyl group with another methoxy group (-OCH3), and the acetal (Ph-CH(OCH3)2) is formed after deprotonation.

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