### 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 ![Cyclopentane](https://www.chemicalland21.com/specialtychem/finechem/CYCLOPENTANE.htm) - **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.

The reactions involves free radical halogenation of cyclopentane and then it's reaction with NaOH to…

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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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

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### 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
![Cyclopentane](https://www.chemicalland21.com/specialtychem/finechem/CYCLOPENTANE.htm)
- **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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