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Alcohols Phenols and Ethers question

2021 · 20 Jul · Shift 1 · Q18
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Alcohols Phenols and Ethers question

2021 · 20 Jul · Shift 1 · Q18

JEE MainChemistryAlcohols Phenols and EthersNumerical+4 / −1
To synthesize 1.0 mole of 2-methylpropan-2-ol from Ethylethanoate ‾\underline{\hspace{2cm}}​ equivalents of CH3MgBrCH_3MgBrCH3​MgBr Reagent will be required. (Integer value)
Numerical answer
View written solutionFree

Correct answer: 2

  1. Identify the target alcohol

    The required product is 2-methylpropan-2-ol, whose structure is: (CH3)3COH(CH_3)_3COH(CH3​)3​COH

    This is a tertiary alcohol.

  2. Reaction of an ester with Grignard reagent

    Ethyl ethanoate is: CH3COOC2H5CH_3COOC_2H_5CH3​COOC2​H5​

    Esters react with Grignard reagents in such a way that 2 moles of Grignard reagent are needed per mole of ester to finally give a tertiary alcohol.

    General reaction: RCOOR′+2R′′MgX→R−C(OMgX)(R′′)2→H3O+R−C(OH)(R′′)2RCOOR' + 2R''MgX \rightarrow R-C(OMgX)(R'')_2 \xrightarrow{H_3O^+} R-C(OH)(R'')_2RCOOR′+2R′′MgX→R−C(OMgX)(R′′)2​H3​O+​R−C(OH)(R′′)2​

  3. Apply to the given case

    Here:

    • Ester: CH3COOC2H5CH_3COOC_2H_5CH3​COOC2​H5​
    • Grignard reagent: CH3MgBrCH_3MgBrCH3​MgBr

    First mole of CH3MgBrCH_3MgBrCH3​MgBr adds to the ester carbonyl, and after elimination of C2H5O−C_2H_5O^-C2​H5​O−, a ketone is formed: CH3COOC2H5+CH3MgBr→CH3COCH3CH_3COOC_2H_5 + CH_3MgBr \rightarrow CH_3COCH_3CH3​COOC2​H5​+CH3​MgBr→CH3​COCH3​ This ketone is propanone (acetone).

    Then a second mole of CH3MgBrCH_3MgBrCH3​MgBr adds to propanone: CH3COCH3+CH3MgBr→(CH3)3COMgBrCH_3COCH_3 + CH_3MgBr \rightarrow (CH_3)_3COMgBrCH3​COCH3​+CH3​MgBr→(CH3​)3​COMgBr

    On hydrolysis: (CH3)3COMgBr→H3O+(CH3)3COH(CH_3)_3COMgBr \xrightarrow{H_3O^+} (CH_3)_3COH(CH3​)3​COMgBrH3​O+​(CH3​)3​COH

  4. Mole ratio

    Thus, to form 1 mole of 2-methylpropan-2-ol2\text{-methylpropan-}2\text{-ol}2-methylpropan-2-ol from 1 mole of ethyl ethanoate, required moles of CH3MgBrCH_3MgBrCH3​MgBr are: 222

  5. Final integer answer

    2\boxed{2}2​

  6. Comparison with stored answer

    Stored correct answer = 2, which matches the derived result.

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