C NMR - chemistry.creighton.educhemistry.creighton.edu/~mhulce/organic/323/323 slides/NMR...
Transcript of C NMR - chemistry.creighton.educhemistry.creighton.edu/~mhulce/organic/323/323 slides/NMR...
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13C NMR
< 13C has 1.1 % natural abundance
� 13C NMR is not very sensitive!
< 13C - 13C spin-spin splitting is never observed
almost no molecules have $ 2 13C in them:
for example, the probability of hexane having two adjacent 13C is
0.011 x 0.011 x 0.29 = 3.5 x 10 -6
< 13C NMR is a carbon counter
tells you the number of chemically nonequivalent carbons
carbons appear in a * 0 - 200 ppm region
< 13C NMR spectra normally are not integrated
peak intensities can be used to guess the “type” of carbon:
usually, CH3 > CH2 > CH > C
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< DEPT 13C NMR spectrum
tells you the number of chemically nonequivalent CH3 , CH2 , and CH carbons
C do not appear–they must be identifed by comparison with the normal 13C NMR spectrum
ways to present a DEPT 13C NMR spectrum:
Q (13C NMR spectrum) + (DEPT-90) + (DEPT-135)
(all carbons) + (only CH carbons) + (CH and CH3 carbons up, CH2 carbons down)
this is the textbook’s method
Q (13C NMR spectrum) + (CH3 subspectrum) + (CH2 subspectrum) + (CH subspectrum) + (all protonated carbons subspectrum)
Q 13C NMR spectrum with CH3 , CH2 , CH , and C resonances labeled
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13C NMR methanol
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13C NMR ethanol
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13C NMR ethyl acetate
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BASIC 13C NMR CHEMICAL SHIFTS
C Type Approximate *, ppm
Alkanes
Methyl 0 - 30
Methylene 15 - 55
Methine 25 - 55
Quaternary 30 - 40
Alkenes
C= C 80 - 145
Alkynes
C/C 70 - 90
Arenes 110 - 170
Benzene 128.7
Alcohols and Ethers
C–O 50 - 90
Amines
C–N 40 - 60
Halogens
C–F 70 - 80
C–Cl 25 - 50
C–Br 10 - 40
C–I -20 - 10
Car bonyls
R2C= O 190 - 220
RXC= O (X = O or N) 150 - 180
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13C NMR of a tribromobenzene, C6H3Br3
What’s the structural formula?
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13C NMR of 1,3,5-tribromobenzene
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13C NMR spectrum of a chloropentane
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Use of DEPT 13C NMR to identify chloropentane structural isomers
A C5H11Cl
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Use of DEPT 13C NMR to identify chloropentane structural isomers CH2 CH2
CH2
CH3
CH2
A C5H11Cl
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Use of DEPT 13C NMR to identify chloropentane structural isomers
CH2
CH
CH3
CH2 CH3
B C5H11Cl
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Use of DEPT 13C NMR to identify chloropentane structural isomers
CH2
CH2
CH3
CH3
C C5H11Cl
CH
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Use of DEPT 13C NMR to identify chloropentane structural isomers
CH3
CH2
D C5H11Cl
CH3
C
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Use of DEPT 13C NMR to identify chloropentane structural isomers
CH3
E C5H11Cl
CH2
C