14. Choose the best reagent from the list below for carrying out each transformation. Place the letter of the reagent in the blank to the left of the reaction. a. C. e. g. 1. 2. 03 Zn, H3O+ CHCl3, KOH 1. 2. OSO4 NaHSO3, H₂O CH₂l2, Zn(Cu) CH3 CH3 CH3 CH3 b. H d. f. h. x CH3 OH CH3 H 1. 2. CH3 OH H₂SO4, HgSO4 heat BH3, THF H₂O2, NaOH, H₂O KMnO4, acid 1. 2. gula Hg(OAC)2, H₂O NaBH4 CH3

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**Problem 14: Reaction Reagent Selection**

Choose the best reagent from the list below for carrying out each transformation. Place the letter of the reagent in the blank to the left of the reaction.

**Reagents:**

a.  
1. \( \text{O}_3 \)  
2. \( \text{Zn, H}_3\text{O}^+ \)  

b.  
1. \( \text{BH}_3 \text{, THF} \)  
2. \( \text{H}_2\text{O}_2 \text{, NaOH, H}_2\text{O} \)  

c. \( \text{CHCl}_3 \text{, KOH} \)  

d. \( \text{H}_2\text{SO}_4 \text{, HgSO}_4 \text{, heat} \)  

e.  
1. \( \text{OsO}_4 \)  
2. \( \text{NaHSO}_3 \text{, H}_2\text{O} \)  

f. \( \text{KMnO}_4 \text{, acid} \)  

g. \( \text{CH}_2\text{I}_2 \text{, Zn(Cu)} \)  

h.  
1. \( \text{Hg(OAc)}_2 \text{, H}_2\text{O} \)  
2. \( \text{NaBH}_4 \)  

**Reactions:**

1. **Reaction 1:**  
   - Starting compound: Methylcyclohexene  
   - Product: Cyclohexanol with a methyl group attached 

2. **Reaction 2:**  
   - Starting compound: Methylcyclohexene  
   - Product: Hexane-1,6-dione

3. **Reaction 3:**  
   - Starting compound: Methylcyclohexene  
   - Product: Cyclopropane with a methyl group

4. **Reaction 4:**  
   - Starting compound: Methylcyclohexene  
   - Product: Cyclohexanol with a methyl group and hydrogen

**Diagrams Explanation:**

1. **Diagram 1:** Shows a double bond in the starting material being converted into an alcohol group on the product, indicative of a hydroxylation reaction.
   
2
Transcribed Image Text:**Problem 14: Reaction Reagent Selection** Choose the best reagent from the list below for carrying out each transformation. Place the letter of the reagent in the blank to the left of the reaction. **Reagents:** a. 1. \( \text{O}_3 \) 2. \( \text{Zn, H}_3\text{O}^+ \) b. 1. \( \text{BH}_3 \text{, THF} \) 2. \( \text{H}_2\text{O}_2 \text{, NaOH, H}_2\text{O} \) c. \( \text{CHCl}_3 \text{, KOH} \) d. \( \text{H}_2\text{SO}_4 \text{, HgSO}_4 \text{, heat} \) e. 1. \( \text{OsO}_4 \) 2. \( \text{NaHSO}_3 \text{, H}_2\text{O} \) f. \( \text{KMnO}_4 \text{, acid} \) g. \( \text{CH}_2\text{I}_2 \text{, Zn(Cu)} \) h. 1. \( \text{Hg(OAc)}_2 \text{, H}_2\text{O} \) 2. \( \text{NaBH}_4 \) **Reactions:** 1. **Reaction 1:** - Starting compound: Methylcyclohexene - Product: Cyclohexanol with a methyl group attached 2. **Reaction 2:** - Starting compound: Methylcyclohexene - Product: Hexane-1,6-dione 3. **Reaction 3:** - Starting compound: Methylcyclohexene - Product: Cyclopropane with a methyl group 4. **Reaction 4:** - Starting compound: Methylcyclohexene - Product: Cyclohexanol with a methyl group and hydrogen **Diagrams Explanation:** 1. **Diagram 1:** Shows a double bond in the starting material being converted into an alcohol group on the product, indicative of a hydroxylation reaction. 2
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