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Hydrocarbons question

2008 · Shift 0 · Q12
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Hydrocarbons question

2008 · Shift 0 · Q12

JEE MainChemistryHydrocarbonsMCQ+4 / −1
The treatment of CH3MgX  C{H_3}MgX\,\,CH3​MgX with CH3C≡C−HC{H_3}C \equiv C - HCH3​C≡C−H produces
  1. A
    CH3−CH=CH2C{H_3} - CH = C{H_2}CH3​−CH=CH2​
  2. B
    CH3C≡C−CH3C{H_3}C \equiv C - C{H_3}CH3​C≡C−CH3​
  3. C
    AIEEE 2008 Chemistry - Hydrocarbons Question 133 English Option 3
  4. D
    CH4C{H_4}CH4​
View written solutionFree

Correct answer: D

  1. Identify the reactants

    The reagent CH3MgXCH_3MgXCH3​MgX is a Grignard reagent. It behaves as a strong base as well as a nucleophile.

    The other reactant is propyne: CH3C≡C−HCH_3C \equiv C-HCH3​C≡C−H

    This is a terminal alkyne, and terminal alkynes contain an acidic hydrogen.

  2. Key concept: Grignard reagent + acidic hydrogen

    Grignard reagents react with compounds containing acidic hydrogen atoms.

    General reaction: RMgX+R′−H→RH+R′MgXRMgX + R'-H \rightarrow RH + R'MgXRMgX+R′−H→RH+R′MgX

    Here:

    • R=CH3−R = CH_3-R=CH3​−
    • R′−H=CH3C≡C−HR'-H = CH_3C \equiv C-HR′−H=CH3​C≡C−H

    So the methyl group abstracts the acidic hydrogen from the terminal alkyne.

  3. Write the reaction

    CH3MgX+CH3C≡C−H→CH4+CH3C≡C−MgXCH_3MgX + CH_3C \equiv C-H \rightarrow CH_4 + CH_3C \equiv C-MgXCH3​MgX+CH3​C≡C−H→CH4​+CH3​C≡C−MgX

    Thus, the organic product formed from the Grignard reagent is methane.

  4. Check the options

    • A: CH3−CH=CH2CH_3-CH=CH_2CH3​−CH=CH2​ → not formed
    • B: CH3C≡C−CH3CH_3C \equiv C-CH_3CH3​C≡C−CH3​ → not formed directly here
    • D: CH4CH_4CH4​ → formed
  5. Final answer

    The product is: CH4\boxed{CH_4}CH4​​

    Hence, Option D is correct.

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