Use the NMR and IR data to identify the structure of the com

Use the NMR and IR data to identify the structure of the compound. Assign which proton belongs to which peak and identify the RELEVANT IR peaks.

Based on the NMRs what is the structure? Assume there is no symmetry and all carbons are unique. CnHmBr. You do not need to assign the vinylic hydrogens 40 80 PPM 60 20 2H 2H 2H 2H 1H 1H 1H PPM

Solution

From carbon spectrum,there are four Sp3 carbon atoms which has values from 25 to 35 ppm and two vinyl carbon atoms which has values at 115 and 140 ppm.From proton spectrum,6 protons at the range from 1.3 to 2.2 ppm,that suggests there are 6 sp3 protons present and these proton containing carbon atoms are at least 1 carbon away from the carbon that contains bromine atom.Protons at 3.5 ppm attached with a carbon atom which is directly attached with bromine atom.Among three vinylic protons 4.8 ppm is for cis proton and 5.2 ppm is for trans proton,5.9 ppm is for the proton which is attached with a carbon atom and that carbon atom contains the alkyl chain.So the desired compound is CH2=CH-CH2-CH2-CH2-CH2-Br.