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Ethyl acetate on reaction with excess o...

Ethyl acetate on reaction with excess of methyl magnesium chloride and dil `H_(2)SO_(4)` gives .

A

dimethyl ketone

B

iso propyl alcohol

C

ethyl aceto acetate

D

t - butyl alcohol

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The correct Answer is:
To solve the question regarding the reaction of ethyl acetate with excess methyl magnesium chloride and dilute H₂SO₄, we can follow these steps: ### Step 1: Identify the Reactants We have ethyl acetate (C₂H₅COOCH₃) and excess methyl magnesium chloride (CH₃MgCl). Methyl magnesium chloride is a Grignard reagent, which acts as a nucleophile. **Hint:** Recognize the structure of ethyl acetate and the role of Grignard reagents in nucleophilic addition reactions. ### Step 2: Nucleophilic Attack The nucleophilic carbon (from the methyl group of the Grignard reagent) will attack the carbonyl carbon of ethyl acetate. This results in the formation of a tetrahedral intermediate. **Hint:** The carbonyl carbon is electrophilic, making it susceptible to nucleophilic attack. ### Step 3: Formation of the Tetrahedral Intermediate The tetrahedral intermediate can be represented as follows: - The oxygen of the carbonyl group becomes negatively charged (O⁻). - The structure now includes a new bond from the methyl group to the carbonyl carbon. **Hint:** Remember that the tetrahedral intermediate is a key step in nucleophilic addition reactions. ### Step 4: Collapse of the Tetrahedral Intermediate The tetrahedral intermediate will collapse, leading to the formation of a ketone (in this case, 3-methylbutan-2-one) and the release of the ethoxy group (C₂H₅O⁻) as a leaving group. **Hint:** Understand that the collapse of the tetrahedral intermediate regenerates the carbonyl functionality. ### Step 5: Second Nucleophilic Attack Since we have excess methyl magnesium chloride, the newly formed ketone (3-methylbutan-2-one) will again be attacked by another molecule of methyl magnesium chloride. This will form a new tetrahedral intermediate. **Hint:** Excess Grignard reagent means that the ketone can be further reacted. ### Step 6: Hydrolysis After the second nucleophilic attack, hydrolysis with dilute H₂SO₄ will convert the intermediate into a tertiary alcohol. The final product will be 2-methyl-2-propanol (tert-butanol). **Hint:** Hydrolysis is crucial for converting the Grignard adduct into the final alcohol product. ### Final Answer The final product of the reaction of ethyl acetate with excess methyl magnesium chloride and dilute H₂SO₄ is **tert-butanol (2-methyl-2-propanol)**. ### Summary of Steps: 1. Identify reactants (ethyl acetate and Grignard reagent). 2. Nucleophilic attack on the carbonyl carbon. 3. Formation of tetrahedral intermediate. 4. Collapse of the intermediate to form a ketone. 5. Second nucleophilic attack by Grignard reagent. 6. Hydrolysis to form tertiary alcohol.

To solve the question regarding the reaction of ethyl acetate with excess methyl magnesium chloride and dilute H₂SO₄, we can follow these steps: ### Step 1: Identify the Reactants We have ethyl acetate (C₂H₅COOCH₃) and excess methyl magnesium chloride (CH₃MgCl). Methyl magnesium chloride is a Grignard reagent, which acts as a nucleophile. **Hint:** Recognize the structure of ethyl acetate and the role of Grignard reagents in nucleophilic addition reactions. ### Step 2: Nucleophilic Attack ...
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Knowledge Check

  • Ethyl amine reacts with excess of methyl iodine to give

    A
    ethyl methyl amine
    B
    ethyl dimethyl amine
    C
    ethyl trimethyl ammonium iodie
    D
    all of these
  • Ethyl amine reacts with excess of methyl iodide to give

    A
    ethyl methyl amine
    B
    ethyl diemthyl amine
    C
    ethyl trimethyl ammonium iodide
    D
    All of these
  • Ethoxy ethane with dil. H_(2)SO_(4) gives

    A
    `C_(2)H_(5)OH`
    B
    `CH_(3) OH, C_(2)H_(5)HSO_(4)`
    C
    `C_(2)H_(5)OH, C_2H_(5)HSO_(4)`
    D
    `CH_(3)OH, C_(2)H_(4)`
  • FIITJEE-CARBOXYLIC ACIDS AND ITS DERIVATIVES-SOLVED PROBLEMS (OBJECTIVE )
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    2. overset(EtONa//EtOH)to (A) underset(EtNo)overset(CH(3)l)to (B) unders...

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    3. Ethyl acetate on reaction with excess of methyl magnesium chloride a...

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    4. The order of reactivity of the following ester towards hydrolysi...

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    5. The correct order of increaese rate of hydrolysis of the following ...

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    6. Which of the following is correct ?

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    7. The correct order of increasing bolling point of the following ...

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    8. Among the given compounds , the most susceptible to nuclephilic a...

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    9. When propanoic acid is treated with aqueous sodium bicarbonate, ...

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    10. underset((ii) CH(3)COCl)overset((i) NaH//THF")to (A) underset((ii) H(2...

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    11. overset(P(2)O(5)) to W underset(H(3)^(+)O)overset(CH(3)MgBr)to X und...

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    12. R - CH(2) - CH(2) - OH can be converted into R - CH(2) - CH(2) - COOH...

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    13. Identify the correct order of boiling points of the following co...

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    14. Chlorination of toluene in presence of light and heat followed by ...

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    15. Reaction of ethyl formate with excess of CH(3)Mgl followed by hyd...

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    16. P as major product must be .

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    17. Which of the following acid undergoes decarboxylation easily ?

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    18. Reaction of R - overset(O)overset(||)(C) - NH(2) with a mixture of B...

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    19. Identify the correct statement(s) about the above sequece of react...

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    20. Which of the following reagents are involved in the following tran...

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