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Consider the following overall reaction and proposed mechanism. Evaluate whether each step of the mechanism is reasonable. For each step that is not reasonable, explain why.

Consider the following overall reaction and proposed mechanism. Evaluate whether each step of the mechanism is reasonable. For each step that is not reasonable, explain why.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Consider the following overall reaction and proposed mechanism. Evaluate whether each step of the mechanism is reasonable. For each step that is not reasonable, explain why. 

**Problem:** Consider the following overall reaction and proposed mechanism. Evaluate whether each step of the mechanism is reasonable. For each step that is not reasonable, explain why. **Overall Reaction:** - A carbonyl group (C=O) on a molecule reacts with methanol (CH₃OH) in the presence of an acid catalyst (H⁺) to form an acetal. **Proposed Mechanism:** 1. **First Intermediate Formation:** - The carbonyl oxygen is protonated by the acid catalyst (H⁺), forming a positively charged oxygen intermediate. This is shown by the movement of a pair of electrons from the oxygen to the hydrogen ion. - The methanol (CH₃OH) attacks the carbonyl carbon, resulting in the breakage of the double bond (C=O) and the formation of a bond between the carbon and oxygen of methanol. - Intermediate structure shows the oxygen from methanol with a positive charge, and the carbon bonded to both original oxygen and methanol. 2. **Second Intermediate Formation:** - The intermediate undergoes further rearrangement. A lone pair from the oxygen atom of methanol helps to push a proton onto the hydroxyl group (OH), converting it into a good leaving group, water (H₂O). - The carbon now forms a double bond with the other oxygen, which is then deprotonated to stabilize and form the acetal product structure. **Key Considerations:** - Evaluate each step for the feasibility of electron movement and the stability of intermediates. - Check if the methanol's oxygen can reasonably share or accept protons. - Consider the likelihood of forming a stable cation and facilitating nucleophilic attack or leaving group formation.
Transcribed Image Text:**Problem:** Consider the following overall reaction and proposed mechanism. Evaluate whether each step of the mechanism is reasonable. For each step that is not reasonable, explain why. **Overall Reaction:** - A carbonyl group (C=O) on a molecule reacts with methanol (CH₃OH) in the presence of an acid catalyst (H⁺) to form an acetal. **Proposed Mechanism:** 1. **First Intermediate Formation:** - The carbonyl oxygen is protonated by the acid catalyst (H⁺), forming a positively charged oxygen intermediate. This is shown by the movement of a pair of electrons from the oxygen to the hydrogen ion. - The methanol (CH₃OH) attacks the carbonyl carbon, resulting in the breakage of the double bond (C=O) and the formation of a bond between the carbon and oxygen of methanol. - Intermediate structure shows the oxygen from methanol with a positive charge, and the carbon bonded to both original oxygen and methanol. 2. **Second Intermediate Formation:** - The intermediate undergoes further rearrangement. A lone pair from the oxygen atom of methanol helps to push a proton onto the hydroxyl group (OH), converting it into a good leaving group, water (H₂O). - The carbon now forms a double bond with the other oxygen, which is then deprotonated to stabilize and form the acetal product structure. **Key Considerations:** - Evaluate each step for the feasibility of electron movement and the stability of intermediates. - Check if the methanol's oxygen can reasonably share or accept protons. - Consider the likelihood of forming a stable cation and facilitating nucleophilic attack or leaving group formation.
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