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Acetone on addition to methyl magnesium ...

Acetone on addition to methyl magnesium bromide forms a complex, which on decomposition with acid gives X and `Mg(OH)Br.` Which one of the following is X?

A

`CH_(3)OH`

B

`(CH_(3))_(3)COH`

C

`(CH_(3))_(2)CHOH`

D

`CH_(3)CH_(2)OH`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we will follow the steps of the reaction between acetone and methyl magnesium bromide (a Grignard reagent) and identify the product formed after hydrolysis. ### Step-by-Step Solution: 1. **Identify the Reactants**: - Acetone (CH₃COCH₃) is a ketone with the structure: ``` CH3 - C(=O) - CH3 ``` - Methyl magnesium bromide (CH₃MgBr) is a Grignard reagent. 2. **Formation of the Grignard Complex**: - When acetone reacts with methyl magnesium bromide, the nucleophilic methyl group (CH₃⁻) from the Grignard reagent attacks the electrophilic carbon of the carbonyl group (C=O) in acetone. - This results in the formation of a tetrahedral intermediate: ``` CH3 - C(OH)(CH3) - CH3 ``` - The magnesium bromide ion (MgBr⁺) associates with the oxygen atom, leading to a complex: ``` CH3 - C(OH)(CH3) - CH3 + MgBr⁺ ``` 3. **Decomposition with Acid**: - Upon hydrolysis (decomposition with acid), the tetrahedral intermediate undergoes protonation and rearrangement. - The negative charge on the oxygen atom is neutralized by a proton (H⁺) from the acid, forming an alcohol: ``` CH3 - C(OH)(CH3) - CH3 → (CH3)3C - OH (tert-butyl alcohol) ``` - The magnesium bromide ion combines with hydroxide ions (OH⁻) from the acid to form: ``` Mg(OH)Br ``` 4. **Identify the Product X**: - The product X formed after hydrolysis is tertiary butyl alcohol, which has the structure: ``` (CH3)3C - OH ``` ### Conclusion: The final product X is **tertiary butyl alcohol**. ### Answer: **X = Tertiary butyl alcohol (Option B)**
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Knowledge Check

  • Which of the following will give acetone?

    A
    `H_(3)C-C-=CHoverset(Hg^(+2),H_(2)SO_(4))rarr`
    B
    `CH_(3)-C-=CHunderset(overset(Theta)OH,H_(2)O)overset(B_(2)H_(6))rarr`
    C
    D
    `HC-=CH+CH_(3)OHrarr`
  • Which one of the following combination gives compound (X)?

    A
    B
    C
    D
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