Fundamentals of Organic ChemistryChemistryBiomolecules
Consider the following sequence of reactions: The major product C is expected to be:
Options
- AMannose
- BFructose
- CArabinose
- DSorbitol
Correct answer
B. Fructose
Step-by-step solution
Reaction of glucose with excess phenylhydrazine ( PhNHNH ₂ ) yields glucosazone (A). Hydrolysis of glucosazone with H ₃ O ^+ and heat removes the phenylhydrazone groups, forming an osone called glucosone (B), which contains an aldehyde group at C-1 and a ketone group at C-2. Reduction of glucosone with Zn/AcOH selectively reduces the more reactive aldehyde group at C-1 to a primary alcohol ( CH ₂ OH ), while the ketone group at C-2 remains intact. This results in the formation of fructose (C). This entire sequence