TWELVE EASY PROBLEMS
COMBINED PROBLEMS FORMULA + INFRARED + NMR
Spectra in these problems were obtained from: SDBSWeb: [Link] 2002)
(Mar
NOTE ON INTEGRALS: Integrals (relative number of hydrogens) are given as: 2 The integrals are the simplest ratio. Expansions are blue and printed above the baseline.
PROBLEM 1 INFRARED SPECTRUM
C4H10 O
COMBINED PROBLEM #1
PROBLEM 1 NMR SPECTRUM 6
C4H10 O
doublet
multiplet
doublet
COMBINED PROBLEM #2
PROBLEM 2 INFRARED SPECTRUM
C9H10 O2
1719
PROBLEM 2 NMR SPECTRUM
C9H10 O2
5
3 2
two multiplets
quartet
triplet
COMBINED PROBLEM #3
PROBLEM 3 INFRARED SPECTRUM
C10H12 O
1688
PROBLEM 3 NMR SPECTRUM
C10H1 2O
septet
doublet
COMBINED PROBLEM #4
PROBLEM 4 INFRARED SPECTRUM
C5H10 O2
1712
PROBLEM 4 NMR SPECTRUM
C5H10 O2
two overlapping multiplets (2 + 2)
triplet
triplet
COMBINED PROBLEM #5
PROBLEM 5 INFRARED SPECTRUM
C9H 12
PROBLEM 5 NMR SPECTRUM
C9H 12
5
septet
doublet
COMBINED PROBLEM #6
PROBLEM 6 INFRARED SPECTRUM
C9H 12
1610
PROBLEM 6 NMR SPECTRUM
C9H 12
1
COMBINED PROBLEM #7
PROBLEM 7 INFRARED SPECTRUM
C6H10 O3
1731
1719
PROBLEM 7 NMR SPECTRUM
C6H10 O3
2 2
3 3
quartet
triplet
COMBINED PROBLEM #8
PROBLEM 8 INFRARED SPECTRUM
C5H7N O2
2266
1749
PROBLEM 8 NMR SPECTRUM
C5H7N O2
2 3
quarte t
triplet
COMBINED PROBLEM #9
PROBLEM 9 INFRARED SPECTRUM
C9H12 O
PROBLEM 9 NMR SPECTRUM
C9H12 O
5
3 1 1 2
triplet
quinte t
triplet
COMBINED PROBLEM #10
PROBLEM 10 INFRARED SPECTRUM
C8H12 O4
1730
PROBLEM 10 NMR SPECTRUM 400 MHz 3
C8H12 O4
1 2
quartet
triplet
COMBINED PROBLEM #11
PROBLEM 11 INFRARED SPECTRUM
C7H12 O4
1735
PROBLEM 11 NMR SPECTRUM 400 MHz 3
C7H12 O4
1 2
quartet
triplet
COMBINED PROBLEM #12
PROBLEM 12 INFRARED SPECTRUM
C8H7 N
2229
PROBLEM 12 NMR SPECTRUM 400 MHz 3
C8H7 N
CORRELATION CHARTS
BASIC INFRARED KNOWLEDGE
BASE VALUES
OH 3600 NH 3400 CH 3000 C N C C C=O C=C 2250 2150 1715 1650 3300 3000 3100
EXPANDED CH
2900
C-H =CH
-C-H
2850 2750
-CHO
CH2 and CH3 bend : 1465 and 1365
1800 1735 1725 1715 1710 1690
C-O 1100
aldehyd acid acid ester e keton chloride e anhydride : 1810 and 1760
amid e
EXPANDED C=O
benzene C=C : between 1400 and 1600 Also remember the effects of H-bonding, conjugation and ring
NMR Correlation Chart
DOWNFIELD DESHIELDED -OH -NH CHCl3 H , UPFIELD SHIELDED TMS
1 2
1 1
1 0
H RCOOH RCHO C= C
(ppm) CH2F CH2Cl CH2Br CH2I CH2O CH2NO 2 CH2Ar CH2NR2 CH2S C C-H C=CCH2 CH2-CO C-CH-C C C-CH2C C-CH3
Ranges can be defined for different general types of protons.
APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS
R-CH3 R-CH2-R R3CH
0.7 - 1.3 1.2 - 1.4 1.4 - 1.7 1.6 - 2.6
R-N-C-H R-S-C-H I-C-H Br-C-H
2.2 - 2.9 2.0 - 3.0 2.0 - 4.0 2.7 - 4.1
R-C=C-H 4.5 6.5 H 6.5 O8.0 R-C-N-H 5.0 9.0 O R-C-H 9.0 10.0 O R-C-O-H 11.0 12.0
R-C=C-C-H O R-C-C-H O
2.1 - 2.4
Cl-C-H 3.1 - 4.1 RO-C-H HO-C-H O R-C-O-C-H O2N-C-H F-C-H 3.2 - 3.8 3.2 - 3.8 3.5 - 4.8 4.1 - 4.3 4.2 - 4.8
RO-C-C-H 2.1 - 2.5 O HO-C-C-H 2.1 - 2.5 N C-C-H 2.1 - 3.0 R-C C-C-H 2.1 - 3.0
C-H 2.3 2.7 R-C C-H 1.7 - 2.7
R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 RR-O-H 0.5 - 5.0 Ar-O-H 4.0 - 1.0 S-H
ALKENES
10
R H C C H R C C H H R C C R R C C R R C C R R C C R R H R H R H H H H R
11 15 s s
12
13
14
Monosubstitute d Disubstitute d cis-1,2-
trans1,21,1-
Trisubstitute d Tetrasubstitute d
=C-H OUT OF PLANE BENDING
100
90
80
70 cm-
BENZENES
10 15
11
12
13 s s
14 s
Monosubstitute d Disubstitute d orth o met a par a Trisubstitute d 1,2, 4 1,2, 3 1,3, 5 s 100 90 80 m s s
RING Hs OOPS m s s m m 70 cm-
combination
