Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the major product formed in the following reaction:
Correct answer
3
Step-by-step solution
The given reactant, 2-methoxy-1,3-pentadiene, contains an enol ether functional group conjugated with an alkene. When treated with dilute H ₂ SO ₄ , the enol ether undergoes acid-catalyzed hydrolysis. The reaction initiates with the protonation of the more electron-rich double bond (the enol ether) at the terminal carbon to form a highly stable, resonance-stabilized oxonium ion: CH ₂= C ( OMe )- CH = CH - CH ₃ H ^+ CH ₃- C ^+( OMe )- CH = CH - CH ₃ CH ₃- C (= O ^+ Me )- CH = CH - CH ₃ Water then acts as a nucleophi