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Consider the reaction, (CH(3))(3)C-und...

Consider the reaction,
`(CH_(3))_(3)C-underset(CH_(3))underset("| ")"CH"-OH+"Conc. HCl"rarrX`.
The product (X) is

A

`(CH_(3))_(3)"CCH"(CH_(3))Cl`

B

`(CH_(3))_(2)"CCl"CH(CH_(3))_(2)`

C

Mixture of both A and B

D

`(CH_(3))_(2)CHCl(Cl)(CH_(3))_(2)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the given reaction, we will analyze the structure of the reactant and the mechanism of the reaction with concentrated HCl. ### Step-by-Step Solution: 1. **Identify the Reactant Structure**: The reactant is (CH₃)₃C-CH₂OH, which can be represented as: ``` CH₃ | CH₃-C-CH₂-OH | CH₃ ``` This is a tertiary alcohol (due to the presence of the -OH group on a carbon that is bonded to three other carbon atoms). 2. **Protonation of the Alcohol**: When concentrated HCl is added, the -OH group of the alcohol gets protonated to form a better leaving group (water): ``` CH₃ | CH₃-C-CH₂-OH + H⁺ → CH₃ | CH₃-C-CH₂-OH₂⁺ | CH₃ ``` 3. **Formation of Carbocation**: The protonated alcohol (oxonium ion) can lose a water molecule (H₂O), leading to the formation of a carbocation: ``` CH₃ | CH₃-C⁺-CH₂ + H₂O | CH₃ ``` 4. **Carbocation Rearrangement**: The carbocation formed is a tertiary carbocation, which is stable. However, to further stabilize it, a methyl group (CH₃) can shift from the adjacent carbon to the carbocation, resulting in a more stable carbocation: ``` CH₃ | CH₃-C-CH₃⁺ | CH₂ ``` 5. **Nucleophilic Attack by Chloride Ion**: The chloride ion (Cl⁻) from HCl will now attack the positively charged carbon to form the final product: ``` CH₃ | CH₃-C-CH₃ | CH₂-Cl ``` 6. **Final Product**: The final product (X) is 2-chloro-2-methylpropane, which can be represented as: ``` CH₃ | CH₃-C-CH₂-Cl | CH₃ ``` ### Final Answer: The product (X) is 2-chloro-2-methylpropane.
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