Question

1. Sketch the NMR spectrum you would expect to find each of the following compounds. a) 1-bromobutane b) 2,2-dibromobutane c) 1-butanol d) 2,2,3,3-tetrabromobutane e) butane ) 1,1,4-tribromobutane g) 1,4-dibromobutane h) 1,1,1-tribromobutane i) vinyl bromide j) 1,1-dibromoethene k) cis-1,2-dibromoethene 1) trans- 1,2-dibromoethene n) 2-methyl-2-butene m) allyl bromide

Answer 1

1) a) 1-bromobutane: a: 0.9 ppm: 3H, E HC Od Br b: 1.3ppm: 2H, sextet c: 1.8ppm: 2H, pentet d: 3.25ppm: 2H, t

2) 2,2-dibromobutane: a: 0.9 ppm: 3H, E b: 1.3ppm: 3H, S c: 1.8ppm: 2H, - H₃C Br 2.0 1.5 1.0 0.5 0.0

c) 1-butanol: н,съаов a: 0.9ppm: 3H, t b: 1.4ppm: 2H, sextet c: 1.7 ppm: 2H, pentet d: 3.3ppm: 2H, t e: variable position, 1H, broad singlet, exchangable 20 0.0

d) 2,2,3,3-tetrabromobutane: Br BrX CH₂ a: 6H, S

d) Butane: a: 0.9 ppm: 6H,t HC CH3 b: 1.25ppm: 4H. a b a

e) 1,1,4-tribromobutane: Br a: 1.9 ppm: 2H, pentet b: 2.1ppm: 2H, pentet c: 3.25ppm: 2H, t d: 4.98ppm: 1H, Bra ċ bd Br 2.02.0

Please note that there are many spectrums to solve, however due to time constraints I am unable to solve all of them.