Question

You’re developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you’ve performed a bromination reaction on phenol. According to the 1H-NMR, what is the product?

1. You're developing a regiospecific electrophilic aromatic substitution catalyst. To determine the regioselectivity, you've performed a bromination reaction on phenol. According to the 1H-NMR, what is the product? (5 pts) OH Bro (1 eq) Electrophilic Catalyst 'H NMR Spectrum (200 MHZ, CDCI, solution) expansion exchanges with D20 10 9 8 7 6 5 4 3 2 8 (ppm)

Answer 1

Br Brz (1 equiv.) Electrophillic catalyst Possible products 1H NMR data show four different peaks in NMR region other than penolic -OH spectra shows that there is two doublet and two triplet pattern with each peak further coupled. This data matches with ortho bromo benzene as each aromatic proton is chemically and magnetically different which is not the case with p-Bromo benzene. OH dd - H Br E 2-bromophenol HYH dd H