Draw the missing products or reagents in the following multistep synthesis. Ignore any inorganic byproducts. Cl2 (1 equiv) I Select to Draw hv NaOH cold DMSO I ■ Draw C5H10O I Select to Draw Na2Cr2O7 H₂O, CH3CO2H I I
Draw the missing products or reagents in the following multistep synthesis. Ignore any inorganic byproducts. Cl2 (1 equiv) I Select to Draw hv NaOH cold DMSO I ■ Draw C5H10O I Select to Draw Na2Cr2O7 H₂O, CH3CO2H I I
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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- **Reagents:** Cl₂ (1 equivalent), hv (light)
- **Intermediate Product:** (Select to Draw)
This step involves the chlorination of cyclopentane using chlorine and light, resulting in the formation of monochlorocyclopentane.
2. **Second Step:**
- **Reagent:** NaOH, cold DMSO
- **Resulting Intermediate Product:** (Select to Draw)
This step involves the substitution of the chlorine atom with a hydroxyl group, producing cyclopentanol.
3. **Third Step:**
- **Reagents:** Na₂Cr₂O₇, H₂O, CH₃CO₂H
- **Final Product:** (Draw C₅H₁₀O)
This step is an oxidation reaction where cyclopentanol is converted into cyclopentanone.
### Explanation of Steps:
1. **Chlorination of Cyclopentane:**
- **Mechanism:** The reaction occurs via a free radical mechanism where Cl₂ is split into two Cl radicals by UV light (hv). One Cl radical abstracts a hydrogen from cyclopentane, forming hydrochloric acid (HCl) and a cyclopentyl radical. The cyclopentyl radical then reacts with another Cl₂ molecule to form monochlorocyclopentane.
2. **Substitution Reaction:**
- **Mechanism:** In the presence of a strong base (NaOH) and a polar aprotic solvent (DMSO), the chlorine atom in monochlorocyclopentane is replaced by a hydroxyl group to form cyclopentanol.
3. **Oxidation of Cyclopentanol:**
- **Mechanism:** Using an oxidizing agent (sodium dichromate, Na₂Cr₂O₇) in an aqueous acidic environment (H₂O, CH₃CO₂H), cyclopentanol is oxidized to cyclopentanone.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fcce22567-888a-4fc7-8d95-6bafc98f7fb0%2F0aa9deed-1176-4370-9c28-799822b1f73f%2Fdzw9ok78_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Multistep Synthesis Problem
**Objective:**
Draw the missing products or reagents in the following multistep synthesis. Ignore any inorganic byproducts.
**Reaction Scheme:**
1. **First Step:**
- **Starting Material:** Cyclopentane
- **Reagents:** Cl₂ (1 equivalent), hv (light)
- **Intermediate Product:** (Select to Draw)
This step involves the chlorination of cyclopentane using chlorine and light, resulting in the formation of monochlorocyclopentane.
2. **Second Step:**
- **Reagent:** NaOH, cold DMSO
- **Resulting Intermediate Product:** (Select to Draw)
This step involves the substitution of the chlorine atom with a hydroxyl group, producing cyclopentanol.
3. **Third Step:**
- **Reagents:** Na₂Cr₂O₇, H₂O, CH₃CO₂H
- **Final Product:** (Draw C₅H₁₀O)
This step is an oxidation reaction where cyclopentanol is converted into cyclopentanone.
### Explanation of Steps:
1. **Chlorination of Cyclopentane:**
- **Mechanism:** The reaction occurs via a free radical mechanism where Cl₂ is split into two Cl radicals by UV light (hv). One Cl radical abstracts a hydrogen from cyclopentane, forming hydrochloric acid (HCl) and a cyclopentyl radical. The cyclopentyl radical then reacts with another Cl₂ molecule to form monochlorocyclopentane.
2. **Substitution Reaction:**
- **Mechanism:** In the presence of a strong base (NaOH) and a polar aprotic solvent (DMSO), the chlorine atom in monochlorocyclopentane is replaced by a hydroxyl group to form cyclopentanol.
3. **Oxidation of Cyclopentanol:**
- **Mechanism:** Using an oxidizing agent (sodium dichromate, Na₂Cr₂O₇) in an aqueous acidic environment (H₂O, CH₃CO₂H), cyclopentanol is oxidized to cyclopentanone.
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