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Basics of Organic Chemistry question

2024 · 4 Apr · Shift 1 · Q2
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Basics of Organic Chemistry question

2024 · 4 Apr · Shift 1 · Q2

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
What will be the decreasing order of basic strength of the following conjugate bases? −OH,RO‾,CH3COO‾,Cl{ }^{-} \mathrm{OH}, \mathrm{R} \overline{\mathrm{O}}, \mathrm{CH}_3 \mathrm{CO} \overline{\mathrm{O}}, \mathrm{Cl}−OH,RO,CH3​COO,Cl
  1. A
    CI‾>RO‾>−OH>CH3COO‾\mathrm{C} \overline{\mathrm{I}}\gt \mathrm{R} \overline{\mathrm{O}}\gt { }^{-} \mathrm{OH}\gt \mathrm{CH}_3 \mathrm{CO} \overline{\mathrm{O}}CI>RO>−OH>CH3​COO
  2. B
    −OH>RO‾>CH3COO‾>C1‾{ }^{-} \mathrm{OH}\gt \mathrm{R} \overline{\mathrm{O}}\gt \mathrm{CH}_3 \mathrm{CO} \overline{\mathrm{O}}\gt \mathrm{C} \overline{1}−OH>RO>CH3​COO>C1
  3. C
    CI‾>−OH>RO‾>CH3COOˉ\mathrm{C} \overline{\mathrm{I}}\gt { }^{-} \mathrm{OH}\gt \mathrm{R} \overline{\mathrm{O}}\gt \mathrm{CH}_3 \mathrm{CO} \bar{O}CI>−OH>RO>CH3​COOˉ
  4. D
    RO‾>−OH>CH3COO‾>C1‾\mathrm{R} \overline{\mathrm{O}}\gt { }^{-} \mathrm{OH}\gt \mathrm{CH}_3 \mathrm{CO} \overline{\mathrm{O}}\gt \mathrm{C} \overline{1}RO>−OH>CH3​COO>C1
View written solutionFree

Correct answer: D

  1. Basic idea

    Basic strength of a conjugate base is inversely proportional to the acidity of its conjugate acid.

    So, compare the conjugate acids of the given bases:

    • \ceOH−\ce{OH^-}\ceOH− has conjugate acid \ceH2O\ce{H2O}\ceH2O
    • \ceRO−\ce{RO^-}\ceRO− has conjugate acid \ceROH\ce{ROH}\ceROH
    • \ceCH3COO−\ce{CH3COO^-}\ceCH3COO− has conjugate acid \ceCH3COOH\ce{CH3COOH}\ceCH3COOH
    • \ceCl−\ce{Cl^-}\ceCl− has conjugate acid \ceHCl\ce{HCl}\ceHCl
  2. Compare conjugate acids

    Their approximate acid strengths are:

    • \ceROH\ce{ROH}\ceROH is a very weak acid
    • \ceH2O\ce{H2O}\ceH2O is also a very weak acid, but alcohols are generally less acidic than water
    • \ceCH3COOH\ce{CH3COOH}\ceCH3COOH is a weak acid, much stronger than water/alcohol
    • \ceHCl\ce{HCl}\ceHCl is a strong acid

    Hence acidity order of conjugate acids is: \ceHCl>CH3COOH>H2O>ROH\ce{HCl > CH3COOH > H2O > ROH}\ceHCl>CH3COOH>H2O>ROH

  3. Therefore, reverse order for basic strength of conjugate bases

    Reverse the above order: \ceRO−>OH−>CH3COO−>Cl−\ce{RO^- > OH^- > CH3COO^- > Cl^-}\ceRO−>OH−>CH3COO−>Cl−

  4. Why this makes sense

    • \ceRO−\ce{RO^-}\ceRO− is stronger base than \ceOH−\ce{OH^-}\ceOH− because alkyl group shows +I+I+I effect and destabilizes the negative charge slightly, making it more eager to accept a proton.
    • \ceCH3COO−\ce{CH3COO^-}\ceCH3COO− is weaker because the negative charge is stabilized by resonance.
    • \ceCl−\ce{Cl^-}\ceCl− is the weakest base because its conjugate acid \ceHCl\ce{HCl}\ceHCl is very strong.
  5. Match with options

    The correct decreasing order is: \ceRO−>OH−>CH3COO−>Cl−\ce{RO^- > OH^- > CH3COO^- > Cl^-}\ceRO−>OH−>CH3COO−>Cl−

    This matches Option D.

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