Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the major product of the following reaction. Conc. H ^+ ?
Correct answer
1
Step-by-step solution
In the presence of concentrated H ^+ , the tertiary allylic alcohol group in the reactant is protonated. Loss of a water molecule generates a tertiary allylic carbocation. This initial carbocation undergoes resonance stabilization. The -electrons of the adjacent double bond shift, moving the positive charge to the carbon atom that is attached to the propanoic acid side chain ( - CH ₂- CH ₂- COOH ). This new carbocation is also tertiary and allylic, making it highly stable. The molecule now has an electrophilic carb