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
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...
icon
Related questions
icon
Concept explainers
Question
100%
### 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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Ethers
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY