Which starting material produces the two products shown after ozonolysis and a reductive workup? 1. O3 ? 2. DMS А. С. В. D.

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### Understanding Ozonolysis in Organic Chemistry

**Question:**
Which starting material produces the two products shown after ozonolysis and a reductive workup?

**Diagram:**

The diagram consists of a chemical reaction setup and four potential starting materials labeled A, B, C, and D.

**Chemical Reaction:**
1. **Reactants and Reagents:** 
   - Reactant: ?
   - First Step: Ozone (O₃)
   - Second Step: DMS (Dimethyl Sulfide)

2. **Products:** 
   - Formaldehyde (structure: H₂C=O)
   - 5-oxohexanal (structure: OHC-(CH₂)₄-CHO)

**Starting Material Options:**
- **A:** Methylcyclopentane (a pentagon with a CH₃ group)
- **B:** Methylcyclopentene (a pentagon with one double bond and a CH₃ group)
- **C:** Cyclohexene (a hexagon with one double bond)
- **D:** Cyclohexane (a hexagon with no double bonds)

**Explanation of Ozonolysis:**
Ozonolysis is an organic reaction where ozone (O₃) is used to cleave alkenes or alkynes. The reaction proceeds as follows: The carbon-carbon double bonds are cleaved, and oxygen atoms are added to form carbonyl groups (C=O). Following this, a reductive workup (commonly using DMS) is performed to yield aldehydes or ketones.

**Answer:**
The correct starting material is **B: Methylcyclopentene**.

**Explanation:**
Methylcyclopentene has a structure that after ozonolysis would produce the two depicted products. The double bond of the cyclopentene breaks, forming formaldehyde (from the double-bonded carbon with no substituents) and 5-oxohexanal (from the other carbon from the double bond and the remaining chain).

Understanding such transformations is crucial in organic synthesis as it allows chemists to predict how molecular structures change during reactions.
Transcribed Image Text:### Understanding Ozonolysis in Organic Chemistry **Question:** Which starting material produces the two products shown after ozonolysis and a reductive workup? **Diagram:** The diagram consists of a chemical reaction setup and four potential starting materials labeled A, B, C, and D. **Chemical Reaction:** 1. **Reactants and Reagents:** - Reactant: ? - First Step: Ozone (O₃) - Second Step: DMS (Dimethyl Sulfide) 2. **Products:** - Formaldehyde (structure: H₂C=O) - 5-oxohexanal (structure: OHC-(CH₂)₄-CHO) **Starting Material Options:** - **A:** Methylcyclopentane (a pentagon with a CH₃ group) - **B:** Methylcyclopentene (a pentagon with one double bond and a CH₃ group) - **C:** Cyclohexene (a hexagon with one double bond) - **D:** Cyclohexane (a hexagon with no double bonds) **Explanation of Ozonolysis:** Ozonolysis is an organic reaction where ozone (O₃) is used to cleave alkenes or alkynes. The reaction proceeds as follows: The carbon-carbon double bonds are cleaved, and oxygen atoms are added to form carbonyl groups (C=O). Following this, a reductive workup (commonly using DMS) is performed to yield aldehydes or ketones. **Answer:** The correct starting material is **B: Methylcyclopentene**. **Explanation:** Methylcyclopentene has a structure that after ozonolysis would produce the two depicted products. The double bond of the cyclopentene breaks, forming formaldehyde (from the double-bonded carbon with no substituents) and 5-oxohexanal (from the other carbon from the double bond and the remaining chain). Understanding such transformations is crucial in organic synthesis as it allows chemists to predict how molecular structures change during reactions.
### Question: 
**What is the major isolated product for this series of reactions?**

### Reaction Sequence:
1. NaNH₂ (3 eq)
2. H₂O
3. NaH
4. CH₃Br
5. HgSO₄, H₂SO₄, H₂O

### Initial Compound:
\[ \begin{matrix} 
   Br \\
     | \\
CH₃-C-CH₃ \\
     | \\
  Br
\end{matrix} \]

### Options for the Major Isolated Product:
A. \[ \begin{array}{c c}
    & - C \equiv C - CH₃
\end{array} \]

B. \[ \begin{array}{c c}
    & - CH₃ - C \equiv C - 
\end{array} \]

C. \[ \begin{array}{c c}
    & CH₃ - CH₂ - C = O
\end{array} \]

D. \[ \begin{array}{c c}
    & CH₃ - C = O - CH₃
\end{array} \]

**Explanation:**
The reaction proceeds in multiple steps involving different reagents. The initial compound undergoes reactions that likely involve substitution and elimination mechanisms, leading to final product formation. Based on the nature of the reagents used:

1. NaNH₂ (sodium amide) is a strong base that can remove acidic protons and facilitate elimination in the first step.
2. H₂O (water) is added in the second step, potentially to terminate the reaction intermediate or hydrate it.
3. NaH (sodium hydride) in the third step is another strong base, often used to deprotonate compounds.
4. CH₃Br (methyl bromide) is likely used as a methylating agent.
5. HgSO₄ (mercuric sulfate), H₂SO₄ (sulfuric acid), and H₂O in the final step suggest a hydration or mercury-catalyzed reaction step, which is typically seen in alkyne reactions forming carbonyl compounds.

Analyzing this information, the major isolated product can be determined from the provided options.
Transcribed Image Text:### Question: **What is the major isolated product for this series of reactions?** ### Reaction Sequence: 1. NaNH₂ (3 eq) 2. H₂O 3. NaH 4. CH₃Br 5. HgSO₄, H₂SO₄, H₂O ### Initial Compound: \[ \begin{matrix} Br \\ | \\ CH₃-C-CH₃ \\ | \\ Br \end{matrix} \] ### Options for the Major Isolated Product: A. \[ \begin{array}{c c} & - C \equiv C - CH₃ \end{array} \] B. \[ \begin{array}{c c} & - CH₃ - C \equiv C - \end{array} \] C. \[ \begin{array}{c c} & CH₃ - CH₂ - C = O \end{array} \] D. \[ \begin{array}{c c} & CH₃ - C = O - CH₃ \end{array} \] **Explanation:** The reaction proceeds in multiple steps involving different reagents. The initial compound undergoes reactions that likely involve substitution and elimination mechanisms, leading to final product formation. Based on the nature of the reagents used: 1. NaNH₂ (sodium amide) is a strong base that can remove acidic protons and facilitate elimination in the first step. 2. H₂O (water) is added in the second step, potentially to terminate the reaction intermediate or hydrate it. 3. NaH (sodium hydride) in the third step is another strong base, often used to deprotonate compounds. 4. CH₃Br (methyl bromide) is likely used as a methylating agent. 5. HgSO₄ (mercuric sulfate), H₂SO₄ (sulfuric acid), and H₂O in the final step suggest a hydration or mercury-catalyzed reaction step, which is typically seen in alkyne reactions forming carbonyl compounds. Analyzing this information, the major isolated product can be determined from the provided options.
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