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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 50d

Propose mechanisms for the following reactions.
(d) Chemical reaction diagram illustrating the conversion of a cyclic acetal to a carbonyl compound and alcohols.

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Step 1: Analyze the starting material, which is a bicyclic acetal. Acetals are typically hydrolyzed under acidic conditions to yield a carbonyl compound and alcohols.
Step 2: Protonation of one of the oxygen atoms in the acetal occurs first, facilitated by the acidic environment (H⁺). This makes the oxygen more electrophilic and susceptible to nucleophilic attack.
Step 3: Water (H₂O) acts as a nucleophile and attacks the carbon atom bonded to the protonated oxygen, leading to the cleavage of one of the C-O bonds and forming an intermediate hemiacetal.
Step 4: The intermediate hemiacetal undergoes further protonation and hydrolysis, resulting in the formation of a ketone (cyclopentanone) and a diol (ethylene glycol, HOCH₂CH₂OH).
Step 5: The final products are cyclopentanone and ethylene glycol, which are formed after the complete hydrolysis of the acetal under acidic conditions.

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