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Me. Ph A ? Me. Ph 1. OsO4 (cat.), NalO4 (2 equiv) tBuOH/H2O 2. OsO4 (cat.) TBHP (1 equiv) tBuOH/H₂O B Ph. Me C Me OH HO H Ph Me D Me. Ph E

Me. Ph A ? Me. Ph 1. OsO4 (cat.), NalO4 (2 equiv) tBuOH/H2O 2. OsO4 (cat.) TBHP (1 equiv) tBuOH/H₂O B Ph. Me C Me OH HO H Ph Me D Me. Ph E

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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What is the starting material for the following sequence?
### Organic Chemistry Puzzle: Reaction Pathway Identification In this educational example, we are given an organic reaction pathway where a starting compound undergoes a transformation to yield one of five possible products (A, B, C, D, E). The reaction involves osmium tetroxide (OsO₄) as a catalyst, which is known for its use in dihydroxylation reactions. #### Reaction Scheme Starting compound: - A complex molecule that includes a benzene ring, a hydroxyl group, and a terminal double bond. The molecule has the following structure: - Benzene (Ph) ring attached to a hydroxyl-substituted, chiral carbon center, which in turn is connected to a terminal double bond and an aldehyde group. Reaction conditions: 1. **First Transformation:** - Reagents: OsO₄ (catalyst), NaIO₄ (2 equivalents), tBuOH/H₂O (tert-butanol/water) - This step likely aims to perform an oxidative cleavage of the double bond. 2. **Second Transformation:** - Reagents: OsO₄ (catalyst), TBHP (1 equivalent, tert-butyl hydroperoxide), tBuOH/H₂O - This step likely continues oxidation, transforming resulting functionalities further. #### Possible Products Five possible products are provided, labeled A, B, C, D, and E. Each product consists of different organic structures, implying that identifying the correct product requires understanding the selective transformations catalyzed by OsO₄ under the given conditions: - **Product A:** - Structure: An α,β-unsaturated ketone - Formula: C₁₀H₁₀O - **Product B:** - Structure: Similar to A but with a different position of the double bond - Formula: C₁₀H₁₀O - **Product C:** - Structure: A diene with phenyl and methyl substitutions - Formula: C₁₁H₁₂ - **Product D:** - Structure: Another ketone with different methyl and phenyl positions - Formula: C₁₀H₁₀O - **Product E:** - Structure: An alkyne - Formula: C₁₀H₁₀
Transcribed Image Text:### Organic Chemistry Puzzle: Reaction Pathway Identification In this educational example, we are given an organic reaction pathway where a starting compound undergoes a transformation to yield one of five possible products (A, B, C, D, E). The reaction involves osmium tetroxide (OsO₄) as a catalyst, which is known for its use in dihydroxylation reactions. #### Reaction Scheme Starting compound: - A complex molecule that includes a benzene ring, a hydroxyl group, and a terminal double bond. The molecule has the following structure: - Benzene (Ph) ring attached to a hydroxyl-substituted, chiral carbon center, which in turn is connected to a terminal double bond and an aldehyde group. Reaction conditions: 1. **First Transformation:** - Reagents: OsO₄ (catalyst), NaIO₄ (2 equivalents), tBuOH/H₂O (tert-butanol/water) - This step likely aims to perform an oxidative cleavage of the double bond. 2. **Second Transformation:** - Reagents: OsO₄ (catalyst), TBHP (1 equivalent, tert-butyl hydroperoxide), tBuOH/H₂O - This step likely continues oxidation, transforming resulting functionalities further. #### Possible Products Five possible products are provided, labeled A, B, C, D, and E. Each product consists of different organic structures, implying that identifying the correct product requires understanding the selective transformations catalyzed by OsO₄ under the given conditions: - **Product A:** - Structure: An α,β-unsaturated ketone - Formula: C₁₀H₁₀O - **Product B:** - Structure: Similar to A but with a different position of the double bond - Formula: C₁₀H₁₀O - **Product C:** - Structure: A diene with phenyl and methyl substitutions - Formula: C₁₁H₁₂ - **Product D:** - Structure: Another ketone with different methyl and phenyl positions - Formula: C₁₀H₁₀O - **Product E:** - Structure: An alkyne - Formula: C₁₀H₁₀
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