1. Please name the unknown compound based on the images below. write notes that reasonably
justify the structure. be as detailed as possible and please write very clearly. WILL RATE
POSITIVE for a detailed answer!! hint: has 2 carbon atoms but no more than 7.
1. identify all major functional groups in the IR spectra.
2. identify all peaks and H and C-NMR spectra.
3. Identify the molecular mass of the unknown from the spectrum.
4. determine the pattern of fragmentation from the mass spectrum
5. generate a molecular formula.
6. determine the index of hydrogen deficiency.
7. Finally, determine the structure of the unknown compound and name it.
PLEASE DONT FORGET THE NAME AND THE STRUCTURE
w many tpes 200 18o 160 14o 120 10o 80 80 40 20 60 COS-00-151 ppm 10 9 6 4 3 2 HPH-00-
188 ppm 100 80 60 20- 10 15 20 25 30 35 40 45 50 55 60 65 70 75 m/ z
Solution
1. IR: The peak at arond 3200 cm-1 corresponds to NH and it being a doublet confirms presence
of NH 2 . The Peak at 2900 corresponds to sp 3
CH stretches or alkane streches. So the molecule
on the whole should be a alkyl primary amine.
2. Carbon NMR shows 2 peaks confirming that there are 2 types of carbon. Of the 2, one of th
epeaks has a higher intensity indicating that there are more carbons of that type. The peak at 44
(CH) should be next to an electronegative atom as it is downfield. So the CH group is next to NH
2

2. 1H NMR shows 2 peaks: one is a septet and the other being a doublet. The septet corresponds to
-CH, sicne the integration is 1 and the doublet has integration of 6, corresponding to 2 CH 3
groups.
3. Molecular mass should be 59.00 g/mol (from mass)
4. Fragmentation in mass:
a. Amines undergo alpha cleavge, leading to loss of a H radical, which gives a M-1 peak at 58.
b. Loss of NH 2 leads to formation of isopropyl carbocation: M-16, peak at 43.
c. Peak at 30 corresponds to immonium ion CH 2 =NH 2
+
5. C 3 H 9 N
6. Index of H deficeiny = 0
7. (CH 3 ) 2 CHNH 2 Propan-2-amine