3 - methyl - 1 - butene on oxymercuration - demercuration yields . . . . . . As the major product

Options

A. 3-methyl-2-butanol
B. 2-methyl-3-butanol
C. 3-methyl-1-butanol
D. 2-methyl-1-butanol

Answer

To solve the problem of what product 3-methyl-1-butene yields upon oxymercuration-demercuration, we can follow these steps:

### Step-by-Step Solution:

1. **Identify the Structure of 3-Methyl-1-Butene**:
- 3-methyl-1-butene is an alkene with the following structure:
```
CH2=CH-CH(CH3)-CH3
```
- This structure indicates a double bond between the first and second carbon atoms, with a methyl group on the third carbon.

2. **Understand Oxymercuration-Demercuration**:
- The process involves two main steps:
1. **Oxymercuration**: The alkene reacts with mercuric acetate (Hg(OAc)2) in the presence of water. This leads to the formation of an organomercury intermediate.
2. **Demercuration**: The organomercury compound is then treated with sodium borohydride (NaBH4), which replaces the mercury with a hydrogen atom.

3. **Apply Markovnikov's Rule**:
- According to Markovnikov's rule, during the addition of water (H2O) to the alkene, the hydroxyl group (OH) will attach to the more substituted carbon atom (the one with fewer hydrogen atoms).
- In this case, the double bond is between C1 and C2. C1 has two hydrogens, while C2 has one hydrogen and is connected to a carbon chain (C3). Thus, the OH group will attach to C2.

4. **Draw the Product Structure**:
- After applying Markovnikov's rule, the addition of water results in:
```
CH3-CH(OH)-CH(CH3)-CH3
```
- This structure indicates that the hydroxyl group is on the second carbon (C2) and a methyl group is on the third carbon (C3).

5. **Name the Product**:
- The compound can be named as 3-methyl-2-butanol, where:
- The longest carbon chain is butanol (4 carbons).
- The hydroxyl group is on the second carbon.
- There is a methyl group on the third carbon.

6. **Select the Correct Answer**:
- Among the provided options, the major product formed from the reaction of 3-methyl-1-butene through oxymercuration-demercuration is:
- **Option 1: 3-methyl-2-butanol**.

### Final Answer:
The major product of the reaction of 3-methyl-1-butene on oxymercuration-demercuration is **3-methyl-2-butanol**.