Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Are the following two reactions valid methods of synthesizing the same organic compound?

### Transcription of Reaction Pathways

This diagram illustrates two reaction mechanisms starting from acetylene (H-C≡C-H).

#### Reaction 1:

1. **Hydrogenation Step:**
   - Reactant: Acetylene (H-C≡C-H)
   - Catalyst: Palladium (Pd)
   - Reagent: Hydrogen (H₂)
   - Product: Ethylene (H₂C=CH₂)

2. **Epoxidation and Acid-Catalyzed Opening:**
   - Reagent: m-CPBA (meta-Chloroperoxybenzoic acid)
   - Intermediate: Epoxide forming an oxirane
   - Additional Catalysts: Sulfuric acid (H₂SO₄) for ring-opening
   - Final Product: 1,2-Ethanediol (OH-CH₂-CH₂-OH)

#### Reaction 2:

1. **Hydrogenation Step:**
   - Reactant: Acetylene (H-C≡C-H)
   - Catalyst: Palladium (Pd)
   - Reagent: Hydrogen (H₂)
   - Product: Ethylene (H₂C=CH₂)

2. **Bromination and Formation of Halohydrin:**
   - Reagent: Br₂ (Bromine), H₂O (Water)
   - Intermediate: Bromonium ion with water opening to form a halohydrin
   - Stereochemistry: Attack of the nucleophile (OH⁻) forms the halohydrin 

3. **Elimination and Hydroboration-Oxidation:**
   - Heat is applied to convert to a cyclic ether
   - Reagents: BH₃ for Hydroboration, followed by H₂O₂ and NaOH (sodium hydroxide) for oxidation
   - Final Product: 1,2-Ethanediol (CH₃-CH₂-OH)

### Diagram Explanation

- **Flow**: Each pathway follows a series of chemical reactions, depicted with arrows indicating the direction of reactions.
- **Green Curved Arrows**: Indicate electron movement during the formation of intermediate structures in the bromination step.

This educational illustration provides a clear view of multiple reaction pathways beginning with the same starting material, highlighting changes in functional groups and molecular structure.
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Transcribed Image Text:### Transcription of Reaction Pathways This diagram illustrates two reaction mechanisms starting from acetylene (H-C≡C-H). #### Reaction 1: 1. **Hydrogenation Step:** - Reactant: Acetylene (H-C≡C-H) - Catalyst: Palladium (Pd) - Reagent: Hydrogen (H₂) - Product: Ethylene (H₂C=CH₂) 2. **Epoxidation and Acid-Catalyzed Opening:** - Reagent: m-CPBA (meta-Chloroperoxybenzoic acid) - Intermediate: Epoxide forming an oxirane - Additional Catalysts: Sulfuric acid (H₂SO₄) for ring-opening - Final Product: 1,2-Ethanediol (OH-CH₂-CH₂-OH) #### Reaction 2: 1. **Hydrogenation Step:** - Reactant: Acetylene (H-C≡C-H) - Catalyst: Palladium (Pd) - Reagent: Hydrogen (H₂) - Product: Ethylene (H₂C=CH₂) 2. **Bromination and Formation of Halohydrin:** - Reagent: Br₂ (Bromine), H₂O (Water) - Intermediate: Bromonium ion with water opening to form a halohydrin - Stereochemistry: Attack of the nucleophile (OH⁻) forms the halohydrin 3. **Elimination and Hydroboration-Oxidation:** - Heat is applied to convert to a cyclic ether - Reagents: BH₃ for Hydroboration, followed by H₂O₂ and NaOH (sodium hydroxide) for oxidation - Final Product: 1,2-Ethanediol (CH₃-CH₂-OH) ### Diagram Explanation - **Flow**: Each pathway follows a series of chemical reactions, depicted with arrows indicating the direction of reactions. - **Green Curved Arrows**: Indicate electron movement during the formation of intermediate structures in the bromination step. This educational illustration provides a clear view of multiple reaction pathways beginning with the same starting material, highlighting changes in functional groups and molecular structure.
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