Deduce the structures of compound A,B,C and D

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Deduce the structures of compound A,B,C and D
**Reaction Sequence and Product Analysis**

1. **Initial Reaction with PCC:**
   - When the diol is treated with excess pyridinium chlorochromate (PCC), Compound A \((\text{C}_7\text{H}_{10}\text{O}_2)\) is formed as the major product.
   - Compound A gives a positive Tollens' test.

2. **Treatment with Ethylene Glycol:**
   - When Compound A is treated with 1 equivalent of ethylene glycol and a catalytic amount of sulfuric acid (\(\text{H}_2\text{SO}_4\)), Compound B \((\text{C}_9\text{H}_{14}\text{O}_2)\) is the major product.
   - Compound B gives a negative Tollens' test.

3. **Reaction with Methyl Magnesium Bromide:**
   - When Compound B is treated with methyl magnesium bromide followed by workup with aqueous acid, Compound C \((\text{C}_8\text{H}_{14}\text{O}_2)\) and ethylene glycol are the major organic products.
   - Compound C gives a positive Tollens' test.

4. **Heating with Hydrazine and Potassium Hydroxide:**
   - When Compound C is heated with hydrazine (\(\text{H}_2\text{NNH}_2\)) and potassium hydroxide (\(\text{KOH}\)), Compound D \((\text{C}_8\text{H}_{16}\text{O})\) is isolated as the major organic product.
   - Compound D gives a negative Tollens' test.

**Note:** There are no graphs or diagrams included in this text.
Transcribed Image Text:**Reaction Sequence and Product Analysis** 1. **Initial Reaction with PCC:** - When the diol is treated with excess pyridinium chlorochromate (PCC), Compound A \((\text{C}_7\text{H}_{10}\text{O}_2)\) is formed as the major product. - Compound A gives a positive Tollens' test. 2. **Treatment with Ethylene Glycol:** - When Compound A is treated with 1 equivalent of ethylene glycol and a catalytic amount of sulfuric acid (\(\text{H}_2\text{SO}_4\)), Compound B \((\text{C}_9\text{H}_{14}\text{O}_2)\) is the major product. - Compound B gives a negative Tollens' test. 3. **Reaction with Methyl Magnesium Bromide:** - When Compound B is treated with methyl magnesium bromide followed by workup with aqueous acid, Compound C \((\text{C}_8\text{H}_{14}\text{O}_2)\) and ethylene glycol are the major organic products. - Compound C gives a positive Tollens' test. 4. **Heating with Hydrazine and Potassium Hydroxide:** - When Compound C is heated with hydrazine (\(\text{H}_2\text{NNH}_2\)) and potassium hydroxide (\(\text{KOH}\)), Compound D \((\text{C}_8\text{H}_{16}\text{O})\) is isolated as the major organic product. - Compound D gives a negative Tollens' test. **Note:** There are no graphs or diagrams included in this text.
The diagram illustrates a multi-step organic synthesis starting with a cyclohexanol derivative and proceeding through several key reactions to reach compound D.

1. **First Step: Oxidation**
   - Starting Material: Cyclohexanol derivative.
   - Reactant: Excess PCC (pyridinium chlorochromate).
   - Product: Compound A with the molecular formula C₇H₁₀O₂.

2. **Second Step: Formation of an Acetal**
   - Reactants: 1 equivalent of ethylene glycol (HOCH₂CH₂OH) and catalytic H₂SO₄ (sulfuric acid).
   - Product: Compound B with the molecular formula C₉H₁₄O₃.

3. **Third Step: Grignard Reaction**
   - Reactants: Methylmagnesium bromide (CH₃MgBr) followed by aqueous acid workup (H₃O⁺).
   - Product: Compound C with the molecular formula C₈H₁₄O₂.

4. **Fourth Step: Wolff-Kishner Reduction**
   - Reactants: Hydrazine (H₂NNH₂), KOH, and heat.
   - Product: Compound D with the molecular formula C₈H₁₆.

Each step represents a typical transformation in organic chemistry, utilizing well-known reagents and conditions to achieve functional group interconversions and structural modifications. This pathway demonstrates the versatility in synthetic strategies to build complex organic molecules.
Transcribed Image Text:The diagram illustrates a multi-step organic synthesis starting with a cyclohexanol derivative and proceeding through several key reactions to reach compound D. 1. **First Step: Oxidation** - Starting Material: Cyclohexanol derivative. - Reactant: Excess PCC (pyridinium chlorochromate). - Product: Compound A with the molecular formula C₇H₁₀O₂. 2. **Second Step: Formation of an Acetal** - Reactants: 1 equivalent of ethylene glycol (HOCH₂CH₂OH) and catalytic H₂SO₄ (sulfuric acid). - Product: Compound B with the molecular formula C₉H₁₄O₃. 3. **Third Step: Grignard Reaction** - Reactants: Methylmagnesium bromide (CH₃MgBr) followed by aqueous acid workup (H₃O⁺). - Product: Compound C with the molecular formula C₈H₁₄O₂. 4. **Fourth Step: Wolff-Kishner Reduction** - Reactants: Hydrazine (H₂NNH₂), KOH, and heat. - Product: Compound D with the molecular formula C₈H₁₆. Each step represents a typical transformation in organic chemistry, utilizing well-known reagents and conditions to achieve functional group interconversions and structural modifications. This pathway demonstrates the versatility in synthetic strategies to build complex organic molecules.
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