1. Additional Office Hour Time Every Thursday, 2-3pm in Mol Sci 4100 (the person leading this office hours will be different each week) BEGINS TOMORROW and will go to the end of the quarter

2. NMR practice problems Sources: Web Spectra: http://www.chem.ucla.edu/~webspectra/ http://www.chem.ucla.edu/~webspectra/ Spectral Database of Organic Compounds (SDBS) http://riodb01.ibase.aist.go.jp/sdbs/cgi- bin/cre_index.cgi LEGEND: -1H means an integration value of “1”, while 2H means an intergration value of “2” etc. - s = singlet - d = doublet - t = triplet - m = multiplet Ch14C, Spring 2012 Prof. Dong

3. Rough 1 H-NMR guidelines Aldehyde10 ppm Aromatic7-9 Vinylic5-7 -OCH 3 3-4 Ketone (α position)2 H-C≡C-R2 -CH 3 0-1 TMS Si(CH 3 ) 4 0 (we use this as reference) For next several slides, the chemical structure and its 1 H-NMR spectra is given to you. Please try to assign as many of the protons to the peaks shown. Confirm the following 4 features: 1.Number of equivalent protons 2.Chemical shift 3.Integration 4.Splitting Also, using the molecular formula, calculate the DBE and confirm that it matches the structure shown

4. Position of peak on 1 H-NMR depends on the “chemical” environment around the proton Each of the molecules below give 1 peak on 1 H-NMR because all the protons experience the same chemical environment

5. Beginner #7, C 14 H 14 10H,m (overlap) 4H,s

6. Beginner #10, C 10 H 10 O 2 3H, s 1H,m

7. Beginner #12 C 6 H 12 O 2 3H,s 2H, t2H, pentet 2H, sextet 3H,t

8. Beginner #27, C 3 H 7 OCl 1H, s 2H, t 2H, pentet

9. Beginner #25, C 4 H 8 O 2H, q 3H, s 3H, t

10. Int1 #1, C 3 H 4 O 1H,d 3H (overlapping peaks)

11. Int2 #13, C 10 H 15 N 2H,m 3H,m 4H,q 6H,t

12. Int#12, C 7 H 9 NO 4H,m 2H,s 3H,s