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N X H 1. LDA 2. Ph O H ? H3O+ (excess) HO Ph O H I `H

N X H 1. LDA 2. Ph O H ? H3O+ (excess) HO Ph O H I `H

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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Draw a complete detailed mechanism for this reaction.

The image depicts a chemical reaction sequence used in organic synthesis. It outlines a transformation starting from a terminal alkyne and an aldehyde to produce a 1,2-diol. ### Reaction Sequence: 1. **Starting Materials:** - **Amine (Left):** An aldimine with a methyl group adjacent to the nitrogen (R = CH₃). - **Aldehyde (Added Intermediate):** Benzaldehyde (PhCHO), where "Ph" denotes a phenyl group. 2. **Reagents and Conditions:** - **Step 1:** Treatment with lithium diisopropylamide (LDA). LDA is a strong base used for deprotonation to form an enolate from benzaldehyde. - **Step 2:** Reaction with benzaldehyde to form an intermediate compound (unspecified). - **Followed by:** Acidic workup with excess hydronium ion (H₃O⁺) in aqueous conditions. 3. **Product:** - A 1,2-diol with a hydroxyl and a carbonyl group: - The structure includes a carbon chain where one carbon is doubly bonded to an oxygen (carbonyl), and two adjacent carbons each bear a hydroxyl group (-OH). - A phenyl group is bonded to the central carbon, indicating a benzylic position. ### Explanation: This sequence likely involves an initial enolate formation, followed by a nucleophilic addition to create a new carbon-carbon bond. The acidic workup facilitates the conversion of intermediate species into the final diol product, specifying syn-diol formation. Each step must be carefully controlled to ensure the correct stereochemistry and product yield. This transformation is a typical example of synthetic strategy in organic chemistry for constructing complex molecules from simpler precursors.
Transcribed Image Text:The image depicts a chemical reaction sequence used in organic synthesis. It outlines a transformation starting from a terminal alkyne and an aldehyde to produce a 1,2-diol. ### Reaction Sequence: 1. **Starting Materials:** - **Amine (Left):** An aldimine with a methyl group adjacent to the nitrogen (R = CH₃). - **Aldehyde (Added Intermediate):** Benzaldehyde (PhCHO), where "Ph" denotes a phenyl group. 2. **Reagents and Conditions:** - **Step 1:** Treatment with lithium diisopropylamide (LDA). LDA is a strong base used for deprotonation to form an enolate from benzaldehyde. - **Step 2:** Reaction with benzaldehyde to form an intermediate compound (unspecified). - **Followed by:** Acidic workup with excess hydronium ion (H₃O⁺) in aqueous conditions. 3. **Product:** - A 1,2-diol with a hydroxyl and a carbonyl group: - The structure includes a carbon chain where one carbon is doubly bonded to an oxygen (carbonyl), and two adjacent carbons each bear a hydroxyl group (-OH). - A phenyl group is bonded to the central carbon, indicating a benzylic position. ### Explanation: This sequence likely involves an initial enolate formation, followed by a nucleophilic addition to create a new carbon-carbon bond. The acidic workup facilitates the conversion of intermediate species into the final diol product, specifying syn-diol formation. Each step must be carefully controlled to ensure the correct stereochemistry and product yield. This transformation is a typical example of synthetic strategy in organic chemistry for constructing complex molecules from simpler precursors.
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