Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the most acidic hydrogen among the indicated hydroxyl groups in the following compound:
Options
- AHydrogen of –OH(d)
- BHydrogen of –OH(b)
- CHydrogen of –OH(a)
- 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