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Alcohols Phenols and Ethers question

2021 · 22 Jul · Shift 2 · Q3
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Alcohols Phenols and Ethers question

2021 · 22 Jul · Shift 2 · Q3

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Which of the following compounds will provide a tertiary alcohol or reaction with excess of CH3MgBrCH_3MgBrCH3​MgBr followed by hydrolysis?
  1. A
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 99 English Option 1
  2. B
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 99 English Option 2
  3. C
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 99 English Option 3
  4. D
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 99 English Option 4
View written solutionFree

Correct answer: A

  1. Key reaction to use

    Grignard reagent CH3MgBrCH_3MgBrCH3​MgBr adds a methyl group to carbonyl compounds, and after hydrolysis gives alcohols.

    The type of alcohol formed depends on the starting compound:

    • From formaldehyde →\rightarrow→ primary alcohol
    • From aldehyde (except formaldehyde) →\rightarrow→ secondary alcohol
    • From ketone →\rightarrow→ tertiary alcohol
    • From esters / acid chlorides with excess Grignard reagent →\rightarrow→ tertiary alcohol (because two alkyl groups from Grignard can ultimately be introduced)
  2. Condition for getting a tertiary alcohol with excess CH3MgBrCH_3MgBrCH3​MgBr

    Therefore, the compound must effectively behave like:

    • a ketone, or
    • an ester / acid derivative that on excess Grignard addition gives a tertiary alcohol.
  3. Issue with the given question

    The options labeled A, B, C, D are not visible in the prompt; they are blank. So the exact structures cannot be independently evaluated.

  4. Comparison with stored answer

    Since the actual options are missing, I cannot derive from the structures which one is correct by direct analysis. However, the stored correct answer is A.

    In the absence of visible options, I cannot rigorously verify it from the data provided. But if option A is the ketone/ester/acid derivative among the choices, then it would indeed give a tertiary alcohol with excess CH3MgBrCH_3MgBrCH3​MgBr followed by hydrolysis.

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