Download - TWELVE EASY PROBLEMS
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TWELVE EASY PROBLEMSTWELVE EASY PROBLEMS
COMBINED PROBLEMS
FORMULA + INFRARED + NMR
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SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (Mar 2002)
Spectra in these problems were obtained from:
Integrals (relative number of hydrogens)
are given as: 2
The integrals are the simplest ratio.
NOTE ON INTEGRALS:
Expansions are blue and printed above the baseline.
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COMBINED PROBLEM #1COMBINED PROBLEM #1
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C4H10O
PROBLEM 1 INFRARED SPECTRUMPROBLEM 1 INFRARED SPECTRUM
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PROBLEM 1 NMR SPECTRUMPROBLEM 1 NMR SPECTRUM
C4H10O
6
1
1
2
doublet multiplet doublet
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Answer to #1
• (CH3)2CHCH2OH
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COMBINED PROBLEM #2COMBINED PROBLEM #2
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C9H10O2
PROBLEM 2 INFRARED SPECTRUMPROBLEM 2 INFRARED SPECTRUM
1719
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PROBLEM 2 NMR SPECTRUMPROBLEM 2 NMR SPECTRUM
C9H10O2
5
23
quartet triplettwo multiplets
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Answer to 2
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COMBINED PROBLEM #3COMBINED PROBLEM #3
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C10H12O
PROBLEM 3 INFRARED SPECTRUMPROBLEM 3 INFRARED SPECTRUM
1688
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PROBLEM 3 NMR SPECTRUMPROBLEM 3 NMR SPECTRUM
C10H12O
5 1
6
doubletseptet
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Answer #3
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COMBINED PROBLEM #4COMBINED PROBLEM #4
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C5H10O2
PROBLEM 4 INFRARED SPECTRUMPROBLEM 4 INFRARED SPECTRUM
1712
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C5H10O2
PROBLEM 4 NMR SPECTRUMPROBLEM 4 NMR SPECTRUM
1
2
3
4
triplettriplet
two overlappingmultiplets (2 + 2)
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Answer
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COMBINED PROBLEM #5COMBINED PROBLEM #5
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C9H12
PROBLEM 5 INFRARED SPECTRUMPROBLEM 5 INFRARED SPECTRUM
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C9H12
PROBLEM 5 NMR SPECTRUMPROBLEM 5 NMR SPECTRUM
5
1
6
septet doublet
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Answer to 5
• Isopropyl benzene
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COMBINED PROBLEM #6COMBINED PROBLEM #6
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C9H12O
PROBLEM 6 INFRARED SPECTRUMPROBLEM 6 INFRARED SPECTRUM
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C9H12O
5
1 12
3
PROBLEM 6 NMR SPECTRUMPROBLEM 6 NMR SPECTRUM
triplet quintet triplet
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Answer 6
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CORRELATION CHARTSCORRELATION CHARTS
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acid
BASIC INFRARED KNOWLEDGEBASIC INFRARED KNOWLEDGE
OH 3600NH 3400
CH 3000
C N 2250C C 2150
C=O 1715
C=C 1650
C-O 1100
3300 3100 2900 2850 2750
3000
1800 1735 1725 1715 1710 1690
=C-H -C-H-CHO
C-H
ketoneesteracidchloride
aldehydeamide
anhydride : 1810 and 1760
CH2 and CH3 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
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NMR Correlation ChartNMR Correlation Chart
12 11 10 9 8 7 6 5 4 3 2 1 0
-OH -NH
CH2FCH2ClCH2BrCH2ICH2OCH2NO2
CH2ArCH2NR2
CH2SC C-HC=C-CH2
CH2-C-O
C-CH-C
C
C-CH2-CC-CH3
RCOOH RCHO C=C
H
TMS
HCHCl3 ,
(ppm)
DOWNFIELD UPFIELD
DESHIELDED SHIELDED
Ranges can be defined for different general types of protons.This chart is general, the next slide is more definite.
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APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS
R-CH3 0.7 - 1.3
R-C=C-C-H 1.6 - 2.6
R-C-C-H 2.1 - 2.4
O
O
RO-C-C-H 2.1 - 2.5O
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-N-C-H 2.2 - 2.9
R-S-C-H 2.0 - 3.0
I-C-H 2.0 - 4.0
Br-C-H 2.7 - 4.1
Cl-C-H 3.1 - 4.1
RO-C-H 3.2 - 3.8
HO-C-H 3.2 - 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
O2N-C-H 4.1 - 4.3
F-C-H 4.2 - 4.8
R3CH 1.4 - 1.7R-CH2-R 1.2 - 1.4 4.5 - 6.5
R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H
R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0
R-C-N-H
O
5.0 - 9.0
1.0 - 4.0R-C C-H 1.7 - 2.7
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Monosubstituted
cis-1,2-
trans-1,2-
1,1-
Trisubstituted
Tetrasubstituted
C CH
R H
H
C CH
R R
H
C CR
H R
H
C CR
R R
R
C CR
R R
H
C CR
R H
H
Disubstituted
10 11 12 13 14 15
1000 900 800 700 cm-1
s s
m
s
s
s
=C-H OUT OF PLANE BENDING
ALKENES
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10 11 12 13 14 15
1000 900 800 700 cm-1
Monosubstituted
Disubstituted
ortho
meta
para
Trisubstituted
1,2,4
1,2,3
1,3,5
BENZENES
s s
s
s s
s
s
s
s
m
m
m
mOOPS
RING H’s
combination bands