Chem 8361/4361: Interpretation of Organic Spectra
Problem Set 1
Due on Sept. 22, 2008
1) Work the following problems in Silverstein:
Chapter 1, 1.6, 1.8, 1.9
Mass
56.0264
73.0896
74.0363
89.0479
94.0535
96.0572
98.0736
100.0893
102.0678
113.0845
114.1043
116.0841
116.1206
122.0733
122.0733
126.1041
138.0687
150.0041
152.0476
156.9934
161.9637
169.9735
208.0094
1.6 (Spectrum)
1.8 (Formula)
1.9 (HDI)
Chapter 2, Student Exercises 2.2, 2.4, 2.5, 2.7, 2.9
notes:
1) For 2.2 “1-Nitropropane dioxane” is two separate compounds: 1-Nitropropane and 1,2dioxane
2) For 2.4, 2.5, and 2.7 the link to the required website can be found on the course website in
the “problem set” area.
3) For 2.9, the peaks you list as being absent should only be those that are diagnostic (e.g.
C=O, OH, NH, etc.). Also for any carbonyls you should list what type (e.g. aldehyde).
2) Propose structures for the following compounds. Be sure to identify key parts of the
spectral data.
2A) MW = 152
2B) C9H12
2C) MW = 94
2D) C10H12O