Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Consider the following reaction: The product mixture will contain:
Options
- ACH ₃ CHO + OHC - NH ₂ + CO ₂
- BCH ₃ CHO + OHC - COOR + NH ₃
- CCH ₃ COOH only
- DCH ₃ COOH + NH ₂ COOR + HCOOH
Correct answer
B. CH ₃ CHO + OHC - COOR + NH ₃
Step-by-step solution
The given reactant is CH₃-CH(OH)-CH(NH₂)-COOR , which contains an -amino alcohol moiety. Periodic acid ( HIO₄ ) oxidatively cleaves the C-C bond of -amino alcohols. The carbon atom bearing the - OH group is oxidized to a carbonyl group, and the carbon atom bearing the - NH₂ group is oxidized to an imine. Cleavage of the bond between CH(OH) and CH(NH₂) yields: CH₃-CH(OH)- CH₃-CHO - CH(NH₂)-COOR HN=CH-COOR In the second step, the intermediate imine undergoes hydrolysis with H₂O to form an aldehyde and ammonia: HN=CH-