2-Chloro-1-phenylbutane `underset(EtOH)overset(NaOH)tounderset(NaBH_(4))overset(Hg(Oac)_(2))to` product is
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Text Solution
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The correct Answer is:
To solve the question step by step, let's break down the reaction process for 2-Chloro-1-phenylbutane with the given reagents.
### Step 1: Identify the Structure of the Substrate
The substrate is 2-Chloro-1-phenylbutane.
- The butane chain has four carbon atoms.
- The phenyl group (C6H5) is attached to the first carbon (C1).
- A chlorine atom (Cl) is attached to the second carbon (C2).
The structure can be represented as:
```
Cl
|
C1 - C2 - C3 - C4
|
Ph
```
### Step 2: Perform E2 Elimination Reaction
The first reagent is NaOH in ethanol (EtOH), which promotes an E2 elimination reaction.
- In E2 elimination, the base (NaOH) abstracts a proton from the β-carbon (C2), while the leaving group (Cl) departs from the α-carbon (C1).
- This results in the formation of a double bond between C1 and C2.
Since the phenyl group is attached to C1, the double bond formed will be between C1 and C2, leading to a more stable alkene due to conjugation with the phenyl ring.
The product after E2 elimination will be:
```
H
|
C1 = C2 - C3 - C4
|
Ph
```
This is 1-phenylbut-2-ene.
### Step 3: Oxymercuration-Demercuration
The next reagents are Hg(OAc)₂ followed by NaBH₄. This sequence is known as oxymercuration-demercuration.
- The oxymercuration step involves the addition of mercuric acetate (Hg(OAc)₂) to the alkene (1-phenylbut-2-ene).
- This reaction adds an -OH group to the more substituted carbon (C2) of the alkene, resulting in the formation of an organomercury intermediate.
### Step 4: Demercuration
- The subsequent treatment with NaBH₄ reduces the organomercury intermediate to form the final alcohol product.
- The -OH group replaces the mercury group, leading to the formation of 2-phenylbutan-2-ol.
The final product can be represented as:
```
OH
|
C1 - C2 - C3 - C4
|
Ph
```
### Final Product
The final product of the reaction is 2-phenylbutan-2-ol.
### Summary
The final product of the reaction of 2-Chloro-1-phenylbutane with NaOH in EtOH followed by Hg(OAc)₂ and NaBH₄ is **2-phenylbutan-2-ol**.
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