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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the most acidic hydrogen among the indicated hydroxyl groups in the following compound:

Options

  1. AHydrogen of –OH(d)
  2. BHydrogen of –OH(b)
  3. CHydrogen of –OH(a)
  4. DHydrogen of –OH(c)

Correct answer

D. Hydrogen of –OH(c)

Step-by-step solution

To determine the most acidic hydrogen, we need to evaluate the stability of the conjugate base formed after the removal of a proton ( H^+ ) from each hydroxyl group. A more stable conjugate base corresponds to a more acidic hydrogen. First, let's classify the indicated hydroxyl groups based on the carbon atoms they are attached to: - –OH(b) and –OH(d) are attached to sp^3 hybridized carbon atoms. They are aliphatic alcohols and are generally less acidic. - –OH(a) and –OH(c) are attached to sp^2 hybridized carbon at

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