Question

A researcher plans to make a library of compounds derived from the coupling of a mono-methyl- substituted 1-naphthol and the diazonium derivative of a mono-substituted hydroxyaniline. How many unique coupling products can be obtained if each different naphthol was reacted with each different diazonium compound? Note that the various reaction products will differ by the placement of the methyl group on the naphthol ring and the hydroxyl group on the phenyl ring. Assume each coupling gives only one product. Show your work.

Answer 1

possible structures of mono-methyl- substituted 1-naphthol :

Possible structures of mono-substituted hydroxyaniline :

Total numbers of effective coupling products : 7 * 3 = 21