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Select to Draw mCPBA Select to Draw OH PBr3 DMF H₂ Lindlar's catalyst HBr Select to Draw HCCNa THF Select to Draw Select to Draw

Select to Draw mCPBA Select to Draw OH PBr3 DMF H₂ Lindlar's catalyst HBr Select to Draw HCCNa THF Select to Draw Select to Draw

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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### Organic Synthesis Pathway Overview #### Reactants and Reagents: 1. **Starting Material:** - \( \text{OH} \) (alcohol group) on an alkyl chain (3 carbons). 2. **Reagent 1:** - **PBr₃ (Phosphorus Tribromide)** - **Solvent: DMF (Dimethylformamide)** 3. **Reagent 2:** - **HCCNa (Sodium Acetylide)** - **Solvent: THF (Tetrahydrofuran)** 4. **Reagent 3:** - **H₂ (Hydrogen)** - **Catalyst: Lindlar's Catalyst** 5. **Reagent 4:** - **mCPBA (m-Chloroperoxybenzoic Acid)** 6. **Reagent 5:** - **HBr (Hydrobromic Acid)** #### Reaction Pathway: 1. **First Step:** - The primary alcohol reacts with PBr₃ in DMF which transforms the alcohol into an alkyl bromide. (The product of this step is indicated as "Select to Draw"). 2. **Second Step:** - The formed alkyl bromide reacts with sodium acetylide (HCCNa) in THF, leading to the formation of an alkyne. (The product of this step is indicated as "Select to Draw"). 3. **Third Step:** - The alkyne undergoes partial reduction with hydrogen gas (H₂) in the presence of Lindlar's Catalyst, producing a cis-alkene. (The product of this step is indicated as "Select to Draw"). 4. **Fourth Step:** - The cis-alkene reacts with mCPBA to form an epoxide. (The product of this step is indicated as "Select to Draw"). 5. **Fifth Step:** - The epoxide reacts with HBr, leading to the ring opening and formation of a bromohydrin. (The product of this step is indicated as "Select to Draw"). #### Diagram Explanation: The diagram uses visual flow with arrows showing the sequence of reactions starting from a primary alcohol. Each intermediate product should be drawn (indicated by "Select to Draw") to accurately follow the changes at each step of
Transcribed Image Text:### Organic Synthesis Pathway Overview #### Reactants and Reagents: 1. **Starting Material:** - \( \text{OH} \) (alcohol group) on an alkyl chain (3 carbons). 2. **Reagent 1:** - **PBr₃ (Phosphorus Tribromide)** - **Solvent: DMF (Dimethylformamide)** 3. **Reagent 2:** - **HCCNa (Sodium Acetylide)** - **Solvent: THF (Tetrahydrofuran)** 4. **Reagent 3:** - **H₂ (Hydrogen)** - **Catalyst: Lindlar's Catalyst** 5. **Reagent 4:** - **mCPBA (m-Chloroperoxybenzoic Acid)** 6. **Reagent 5:** - **HBr (Hydrobromic Acid)** #### Reaction Pathway: 1. **First Step:** - The primary alcohol reacts with PBr₃ in DMF which transforms the alcohol into an alkyl bromide. (The product of this step is indicated as "Select to Draw"). 2. **Second Step:** - The formed alkyl bromide reacts with sodium acetylide (HCCNa) in THF, leading to the formation of an alkyne. (The product of this step is indicated as "Select to Draw"). 3. **Third Step:** - The alkyne undergoes partial reduction with hydrogen gas (H₂) in the presence of Lindlar's Catalyst, producing a cis-alkene. (The product of this step is indicated as "Select to Draw"). 4. **Fourth Step:** - The cis-alkene reacts with mCPBA to form an epoxide. (The product of this step is indicated as "Select to Draw"). 5. **Fifth Step:** - The epoxide reacts with HBr, leading to the ring opening and formation of a bromohydrin. (The product of this step is indicated as "Select to Draw"). #### Diagram Explanation: The diagram uses visual flow with arrows showing the sequence of reactions starting from a primary alcohol. Each intermediate product should be drawn (indicated by "Select to Draw") to accurately follow the changes at each step of
**Multistep Synthesis Reaction Pathway** ### Task Draw the missing products or reagents in the following multistep synthesis. Ignore any inorganic byproducts. #### Step-by-Step Reaction Process 1. **Reactant** - Chemical Structure: ``` CH3CH2CH2OH (1-Propanol) ``` 2. **First Reaction: Bromination** - Reagents: \( \text{PBr}_3 \), \( \text{DMF} \) - Expected Transformation: ``` 1-Propanol --> 1-Bromopropane ``` - Missing Structure for 1-Bromopropane. 3. **Second Reaction: Nucleophilic Substitution** - Reagent: Na-C≡CH (Sodium Acetylide), \( \text{THF} \) - Expected Transformation: ``` 1-Bromopropane --> 1-Butyne ``` - Missing Structure for 1-Butyne. 4. **Third Reaction: Partial Hydrogenation** - Reagents: \( \text{H}_2 \), Lindlar's Catalyst - Expected Transformation: ``` 1-Butyne --> cis-2-Butene ``` - Missing Structure for cis-2-Butene. 5. **Fourth Reaction: Epoxidation** - Reagent: mCPBA - Expected Transformation: ``` cis-2-Butene --> cis-2-Butene Oxide ``` - Missing Structure for cis-2-Butene Oxide. In each step, a specific chemical transformation is exhibited. Please select and draw the corresponding missing structures for a complete synthetic pathway.
Transcribed Image Text:**Multistep Synthesis Reaction Pathway** ### Task Draw the missing products or reagents in the following multistep synthesis. Ignore any inorganic byproducts. #### Step-by-Step Reaction Process 1. **Reactant** - Chemical Structure: ``` CH3CH2CH2OH (1-Propanol) ``` 2. **First Reaction: Bromination** - Reagents: \( \text{PBr}_3 \), \( \text{DMF} \) - Expected Transformation: ``` 1-Propanol --> 1-Bromopropane ``` - Missing Structure for 1-Bromopropane. 3. **Second Reaction: Nucleophilic Substitution** - Reagent: Na-C≡CH (Sodium Acetylide), \( \text{THF} \) - Expected Transformation: ``` 1-Bromopropane --> 1-Butyne ``` - Missing Structure for 1-Butyne. 4. **Third Reaction: Partial Hydrogenation** - Reagents: \( \text{H}_2 \), Lindlar's Catalyst - Expected Transformation: ``` 1-Butyne --> cis-2-Butene ``` - Missing Structure for cis-2-Butene. 5. **Fourth Reaction: Epoxidation** - Reagent: mCPBA - Expected Transformation: ``` cis-2-Butene --> cis-2-Butene Oxide ``` - Missing Structure for cis-2-Butene Oxide. In each step, a specific chemical transformation is exhibited. Please select and draw the corresponding missing structures for a complete synthetic pathway.
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