Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Fehling's solution can be used to distinguish between which of the following pairs of compounds?
Options
- ANone of the above pairs
- BCH ₃ CHO and CH ₃ COCH ₂ OH
- CBoth of the above pairs
- DCH ₃ CHO and C ₆ H ₅ CHO
Correct answer
D. CH ₃ CHO and C ₆ H ₅ CHO
Step-by-step solution
Fehling's solution is a mild oxidizing agent used to differentiate aliphatic aldehydes from aromatic aldehydes and ketones. Aliphatic aldehydes like CH ₃ CHO reduce Fehling's solution to form a red precipitate of Cu ₂ O . Aromatic aldehydes like C ₆ H ₅ CHO do not reduce Fehling's solution. -hydroxy ketones like CH ₃ COCH ₂ OH also reduce Fehling's solution because they tautomerize into an enediol intermediate in the alkaline medium, which then gets oxidized. Thus, both CH ₃ CHO and CH ₃ COCH ₂ OH give a positive F