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(CH(3))(3)C-overset(O)overset(||)C-Cl+Li...

`(CH_(3))_(3)C-overset(O)overset(||)C-Cl+LiAlH_(4)" (excess)" to overset(H_(3)O^(o+))to X,X` is

A

`(CH_(3))_(3)C-overset(O)overset(||)C-H`

B

`CH_(3)-underset(CH_(3))underset(|)overset(CH_(3))overset(|)C-CH_(2)-OH`

C

`CH_(3)-underset(CH_(3))underset(|)(CH)-CH_(2)-CH_(2)-OH`

D

`CH_(3)-CH_(2)-CH_(2)-CH_(2)-CH_(2)-OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the reaction of the compound `(CH₃)₃C-C(=O)Cl` (which is a carbonyl compound with a chlorine atom) with Lithium Aluminum Hydride (LiAlH₄) in excess, followed by treatment with H₃O⁺ (acidic workup). ### Step-by-Step Solution: 1. **Identify the Reactant:** The reactant is `(CH₃)₃C-C(=O)Cl`, which can be broken down as follows: - It has a carbon chain with three methyl groups (tert-butyl group) attached to a carbon that is double-bonded to oxygen (carbonyl) and has a chlorine atom. 2. **First Reaction with LiAlH₄:** Lithium Aluminum Hydride (LiAlH₄) is a strong reducing agent. When it reacts with the carbonyl compound, it will provide a hydride ion (H⁻) that will attack the carbon atom of the carbonyl group. - The hydride ion attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate. The oxygen atom will gain a negative charge. 3. **Formation of Aldehyde:** After the hydride attack, the tetrahedral intermediate will collapse, resulting in the elimination of the chlorine atom (Cl⁻) as a leaving group. This will convert the carbonyl compound into an aldehyde: - The product at this stage is `(CH₃)₃C-CHO` (tert-butyl aldehyde). 4. **Second Reaction with Excess LiAlH₄:** Since LiAlH₄ is in excess, it will react again with the aldehyde. The hydride ion will again attack the carbonyl carbon of the aldehyde. - This leads to the formation of another tetrahedral intermediate, where the oxygen now has a negative charge. 5. **Formation of Alcohol:** The tetrahedral intermediate will again collapse, and the oxygen will be protonated by the subsequent treatment with H₃O⁺ (acidic workup). This will lead to the formation of an alcohol: - The final product is `(CH₃)₃C-CH₂OH` (tert-butyl alcohol). ### Final Answer: The final product (X) after the reaction is `(CH₃)₃C-CH₂OH`.
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