1. COMBINED PROBLEM #1

2. C 4 H 10 O PROBLEM 1 INFRARED SPECTRUM

3. PROBLEM 1 NMR SPECTRUM C 4 H 10 O 6 1 1 2 doubletmultipletdoublet

4. COMBINED PROBLEM #2

5. C 9 H 10 O 2 PROBLEM 2 INFRARED SPECTRUM 1719

6. PROBLEM 2 NMR SPECTRUM C 9 H 10 O 2 5 2 3 quartettriplettwo multiplets

7. acid BASIC INFRARED KNOWLEDGE OH3600 NH3400 CH3000 C N2250 C C2150 C=O1715 C=C1650 C-O1100 33003100 2900 2850 2750 3000 180017351725171517101690 =C-H-C-H -CHO C-H ketone esteracid chloride aldehyde amide anhydride : 1810 and 1760 CH 2 and CH 3 bend : 1465 and 1365 BASE VALUES Also remember the effects of H-bonding, conjugation and ring size. benzene C=C : between 1400 and 1600 EXPANDED CH EXPANDED C=O

8. NMR Correlation Chart 1211109876543210 -OH-NH CH 2 F CH 2 Cl CH 2 Br CH 2 I CH 2 O CH 2 NO 2 CH 2 Ar CH 2 NR 2 CH 2 S C C-H C=C-CH 2 CH 2 -C- O C-CH-C C C-CH 2 -C C-CH 3 RCOOHRCHO C=C H TMS CHCl 3,  (ppm) DOWNFIELDUPFIELD DESHIELDEDSHIELDED Ranges can be defined for different general types of protons. This chart is general, the next slide is more definite.

9. APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS R-CH 3 0.7 - 1.3 R-C=C-C-H1.6 - 2.6 R-C-C-H2.1 - 2.4 O O RO-C-C-H2.1 - 2.5 O HO-C-C-H2.1 - 2.5 N C-C-H2.1 - 3.0 R-C C-C-H2.1 - 3.0 C-H 2.3 - 2.7 R-N-C-H2.2 - 2.9 R-S-C-H2.0 - 3.0 I-C-H2.0 - 4.0 Br-C-H2.7 - 4.1 Cl-C-H3.1 - 4.1 RO-C-H3.2 - 3.8 HO-C-H3.2 - 3.8 R-C-O-C-H 3.5 - 4.8 O R-C=C-H H 6.5 - 8.0 R-C-H O 9.0 - 10.0 R-C-O-H O 11.0 - 12.0 O 2 N-C-H4.1 - 4.3 F-C-H4.2 - 4.8 R 3 CH1.4 - 1.7 R-CH 2 -R1.2 - 1.4 4.5 - 6.5 R-N-H0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H R-O-H0.5 - 5.0 Ar-O-H 4.0 - 7.0 R-C-N-H O 5.0 - 9.0 1.0 - 4.0 R-C C-H1.7 - 2.7

10. Monosubstituted cis-1,2- trans-1,2- 1,1- Trisubstituted Tetrasubstituted Disubstituted 10 11 12 13 14 15 1000900800700cm -1 ss m s s s  =C-H OUT OF PLANE BENDING ALKENES

11. 10 11 12 13 14 15 1000900800700cm -1 Monosubstituted Disubstituted ortho meta para Trisubstituted 1,2,4 1,2,3 1,3,5 BENZENES  ss s ss s s s s m m m m OOPS RING H’s combination bands