5. Which of the following diols are likely to undergo oxidative cleavage with H;CrO4? Select all that apply. OH OH OH Он II III HO. IV

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**Chemistry Questions and Exercises**

**5. Which of the following diols are likely to undergo oxidative cleavage with \( \text{H}_2\text{CrO}_4 \)? Select all that apply:**

   **Diagram of diols:**

   - Structure I: Cyclopentane with diol at 1,2-position
   - Structure II: Cyclopentane with diol at 1,3-position
   - Structure III: Cyclohexane with diol at 1,2-position
   - Structure IV: Cyclohexane with diol at 1,3-position (axial and equatorial)
   - Structure V: Cyclohexane with diol at 1,2-position (axial and axial)

**6. Draw the most stable enol tautomer of 8-methylcycloocta-3,5-dien-1-one:**

   - Structure of 8-methylcycloocta-3,5-dien-1-one is provided, showing a cyclooctene ring with a ketone and methyl group.

**7. Rank the following enols in order of increasing stability:**

   **Diagram of enols:**

   - Structure I: Cyclohexene with hydroxyl at 1-position
   - Structure II: Cyclohexene with hydroxyl at 2-position
   - Structure III: Cyclohexene with hydroxyl at 3-position

**8. Using the correct catalysts and solvents, what are the likely product outcomes of steps I and III of the following reaction?**

   - Reaction scheme showing a compound undergoing a reaction with the sequence: 
     1. \( \text{PBr}_3 \)
     2. \( \text{Br}_2 \)
     3. \( \text{H}_2\text{O} \)

   - Initial compound: A carboxylic acid with a methyl group at the 3-position and a cyclohexane ring.
Transcribed Image Text:**Chemistry Questions and Exercises** **5. Which of the following diols are likely to undergo oxidative cleavage with \( \text{H}_2\text{CrO}_4 \)? Select all that apply:** **Diagram of diols:** - Structure I: Cyclopentane with diol at 1,2-position - Structure II: Cyclopentane with diol at 1,3-position - Structure III: Cyclohexane with diol at 1,2-position - Structure IV: Cyclohexane with diol at 1,3-position (axial and equatorial) - Structure V: Cyclohexane with diol at 1,2-position (axial and axial) **6. Draw the most stable enol tautomer of 8-methylcycloocta-3,5-dien-1-one:** - Structure of 8-methylcycloocta-3,5-dien-1-one is provided, showing a cyclooctene ring with a ketone and methyl group. **7. Rank the following enols in order of increasing stability:** **Diagram of enols:** - Structure I: Cyclohexene with hydroxyl at 1-position - Structure II: Cyclohexene with hydroxyl at 2-position - Structure III: Cyclohexene with hydroxyl at 3-position **8. Using the correct catalysts and solvents, what are the likely product outcomes of steps I and III of the following reaction?** - Reaction scheme showing a compound undergoing a reaction with the sequence: 1. \( \text{PBr}_3 \) 2. \( \text{Br}_2 \) 3. \( \text{H}_2\text{O} \) - Initial compound: A carboxylic acid with a methyl group at the 3-position and a cyclohexane ring.
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