Naproxen: spot the regiochemistry flaw
Single questionThree-step route to naproxen: methylate the naphthol, Friedel-Crafts acetylate, then install the alpha-propionic acid. The reaction classes and reagents look right. Check where the acetyl group lands on the naphthalene.
Friedel-Crafts acylation on naphthalene
Methoxy directing effects across naphthalene rings
Regiochemistry of 2-methoxynaphthalene electrophilic substitution
Find the flaw
Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.