In an attempt to brominate butyraldehyde, a student learned a valuable lesson regarding solvent compatibility with reaction conditions, Specifically how strong acids and THF are incompatible. Given the 'H NMR spectrum and molecular formula propose a structure for the MAJOR product. Br2 THF 0 C H + C,H, Bro THF Br minor major major product 35 2007 1661 086T 1.967 1954 1.758 1.744 1.730 912'T 1.702 1423 1420 CH, Bro 500 MHZ *H NMR spectrum in COCI, Source: Chris Jeffrey, Tom Hoye 1417 2.03 204 2.07 2.07 9 EOT 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 2.8 2.6 2.4 2.2 3.0 ppm 2.0 1.8 1.6 1.4 1.2