Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by oxymercuration. CH3- CHOH 1. Hg(OAc)2, H₂O ? 2. NaBH4 CH3CH₂CH₂CHCH₂CH₂CH₂CH3

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**Drawing Structural Formulas for Alkenes in Oxymercuration Reactions**

*Objective:*
Determine the structural formulas for all alkenes that could be used to prepare the specified alcohol using the oxymercuration process.

*Process:*
The reaction specified here involves the transformation of an alkene into an alcohol via oxymercuration-demercuration. The reactants and conditions are as follows:
1. **Hg(OAc)2, H2O**
2. **NaBH4**

*Target Alcohol Structure:*
The desired alcohol product has the following structure:
```
    CH3
     |
     CHOH
     |
CH3CH2CH2CH2CHCH2CH2CH2CH3
```

This molecule is 4-methyl-1-decanol.

*Task:*
Identify all possible alkenes that could lead to this target alcohol upon undergoing the oxymercuration-demercuration process.

*Detailed Examination:*

For oxymercuration to give the tertiary alcohol (4-methyl-1-decanol), the double bond must be present between the fourth and fifth carbon atoms in all cases to place the OH group at the correct position on the carbon chain. We explore each potential alkene isomer in this context:

1. **4-Methyl-1-decene:**
   ```
   CH3CH2CH2CH2CH=CHCH2CH2CH3
   ```
   
   In this structure, the double bond between the 4th and 5th carbon atoms ensures correct placement of the hydroxyl group after oxymercuration.

2. **5-Methyl-2-decene:**
   ```
   CH3CH2CH2CH2C(CH3)=CHCH2CH2CH3
   ```

   By positioning the double bond between the 4th and 5th carbons, we again get the desired product upon reaction.

By examining stereochemistry and possible chain branching, these two isomers are relevant for synthesis via oxymercuration to achieve the target product.

*Conclusion:*
The alkenes suitable for producing 4-methyl-1-decanol via oxymercuration-demercuration are primarily 4-methyl-1-decene and 5-methyl-2-decene. Both these alkenes, upon correct reaction conditions, will yield the required tertiary alcohol.

*Note:* The hypothetical question mark in the react
Transcribed Image Text:**Drawing Structural Formulas for Alkenes in Oxymercuration Reactions** *Objective:* Determine the structural formulas for all alkenes that could be used to prepare the specified alcohol using the oxymercuration process. *Process:* The reaction specified here involves the transformation of an alkene into an alcohol via oxymercuration-demercuration. The reactants and conditions are as follows: 1. **Hg(OAc)2, H2O** 2. **NaBH4** *Target Alcohol Structure:* The desired alcohol product has the following structure: ``` CH3 | CHOH | CH3CH2CH2CH2CHCH2CH2CH2CH3 ``` This molecule is 4-methyl-1-decanol. *Task:* Identify all possible alkenes that could lead to this target alcohol upon undergoing the oxymercuration-demercuration process. *Detailed Examination:* For oxymercuration to give the tertiary alcohol (4-methyl-1-decanol), the double bond must be present between the fourth and fifth carbon atoms in all cases to place the OH group at the correct position on the carbon chain. We explore each potential alkene isomer in this context: 1. **4-Methyl-1-decene:** ``` CH3CH2CH2CH2CH=CHCH2CH2CH3 ``` In this structure, the double bond between the 4th and 5th carbon atoms ensures correct placement of the hydroxyl group after oxymercuration. 2. **5-Methyl-2-decene:** ``` CH3CH2CH2CH2C(CH3)=CHCH2CH2CH3 ``` By positioning the double bond between the 4th and 5th carbons, we again get the desired product upon reaction. By examining stereochemistry and possible chain branching, these two isomers are relevant for synthesis via oxymercuration to achieve the target product. *Conclusion:* The alkenes suitable for producing 4-methyl-1-decanol via oxymercuration-demercuration are primarily 4-methyl-1-decene and 5-methyl-2-decene. Both these alkenes, upon correct reaction conditions, will yield the required tertiary alcohol. *Note:* The hypothetical question mark in the react
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