COMBINED PROBLEM #1

C 4 H 10 O PROBLEM 1 INFRARED SPECTRUM

PROBLEM 1 NMR SPECTRUM C 4 H 10 O doubletmultipletdoublet

COMBINED PROBLEM #2

C 9 H 10 O 2 PROBLEM 2 INFRARED SPECTRUM 1719

PROBLEM 2 NMR SPECTRUM C 9 H 10 O quartettriplettwo multiplets

acid BASIC INFRARED KNOWLEDGE OH3600 NH3400 CH3000 C N2250 C C2150 C=O1715 C=C1650 C-O =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

NMR Correlation Chart 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.

APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS R-CH R-C=C-C-H R-C-C-H O O RO-C-C-H O HO-C-C-H N C-C-H R-C C-C-H C-H R-N-C-H R-S-C-H I-C-H Br-C-H Cl-C-H RO-C-H HO-C-H R-C-O-C-H O R-C=C-H H R-C-H O R-C-O-H O O 2 N-C-H F-C-H R 3 CH R-CH 2 -R R-N-H Ar-N-H R-S-H R-O-H Ar-O-H R-C-N-H O R-C C-H

Monosubstituted cis-1,2- trans-1,2- 1,1- Trisubstituted Tetrasubstituted Disubstituted cm -1 ss m s s s  =C-H OUT OF PLANE BENDING ALKENES

cm -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