The main organic product of the reaction of neopentyl bromide with aqueous NaOH is

Options

A. Neopentyl alcohol
B. Isobutyl alcohol
C. 3-Methylbutan-2-ol
D. 2-Methylbutan-2-ol

Explanation

To determine the main organic product of the reaction of neopentyl bromide with aqueous NaOH, we will follow these steps:

### Step 1: Identify the Structure of Neopentyl Bromide
Neopentyl bromide has the following structure:
- It consists of a central carbon atom bonded to four groups: three methyl groups (CH₃) and one bromine atom (Br).
- The structure can be represented as:
```
CH3
|
CH3 - C - CH2 - Br
|
CH3
```

### Step 2: Mechanism of Reaction
The reaction of neopentyl bromide with aqueous NaOH will proceed via an SN1 mechanism:
- In an SN1 reaction, the first step is the formation of a carbocation after the leaving group (Br) departs.
- The bromine atom leaves, resulting in the formation of a carbocation:
```
CH3
|
CH3 - C⁺ - CH2
|
CH3
```

### Step 3: Stability of Carbocation
- The carbocation formed is a primary (1°) carbocation, which is not very stable.
- To increase stability, a rearrangement can occur. In this case, a 1,2-methyl shift can take place where one of the methyl groups shifts to the adjacent carbon, leading to a more stable tertiary (3°) carbocation:
```
CH3
|
CH3 - C - CH2
|
CH3
```
After the shift, the structure becomes:
```
CH3
|
CH3 - C⁺ - CH3
|
CH2
```

### Step 4: Nucleophilic Attack
- The hydroxide ion (OH⁻) from NaOH acts as a nucleophile and attacks the positively charged carbon of the tertiary carbocation:
```
CH3
|
CH3 - C - OH
|
CH2
```

### Step 5: Final Product
- The final product of this reaction is 2-methylbutan-2-ol. The IUPAC naming involves:
- Counting the longest carbon chain (4 carbons) and identifying the position of the hydroxyl group (OH) and the methyl group (CH₃).
- The correct name is 2-methylbutan-2-ol.

### Conclusion
The main organic product of the reaction of neopentyl bromide with aqueous NaOH is **2-methylbutan-2-ol**.

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