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ClCH2 CH3
ClCH2CH2CH2CH2CH3
10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
ClCH2CH2CH2CH2CH3
a separate, distinct
peak appears for
each of the 5
carbons CDCl3
A) B)
C) D)
13C Chemical Shifts
A. A = 7; B = 3; C = 1; D = 1; E = 3
B. A = 7; B = 4; C = 0; D = 3; E = 2
C. A = 7; B = 3; C = 1; D = 2; E = 2
D. A = 8; B = 4; C = 0; D = 1; E = 3
E. A = 8; B = 4; C = 1; D = 2; E = 1
Types of Carbons
CH4 0.2 -2
CH3CH3 primary 0.9 8
CH3CH2CH3 secondary 1.3 16
(CH3)3CH tertiary 1.7 25
(CH3)4C quaternary 28
Replacing H with C (more electronegative) deshields
C to which it is attached.
Electronegativity Effects on CH3
Chemical shift, d
1H 13C
CH4 0.2 -2
CH3NH2 2.5 27
CH3OH 3.4 50
CH3F 4.3 75
Electronegativity Effects and Chain Length
Chemical 45 33 29 22 14
shift, d
sp3 hybridized
carbon is more
114 36
shielded than sp2.
138 36 126-142
sp hybridized
carbon is
more H C C CH2 CH2 CH3
shielded than 68 84 22 20 13
sp2, but less
shielded than
sp3.
Carbonyl Carbons are Especially Deshielded
Type of carbon Chemical shift (d), Type of carbon Chemical shift (d),
ppm ppm
R3CH 25-50
110-175
R4C 30-40
Table
Type of carbon Chemical shift (d), Type of carbon Chemical shift (d),
ppm ppm
RCH2OH 50-65 O
A) B)
C) D)
Proton-Decoupled 13C NMR of
2-Butanol
Using DEPT to Count the Hydrogens
Attached to 13C
Distortionless Enhancement
of Polarization Transfer
(De-coupling)
Measuring a 13C NMR spectrum involves
CCH2CH2CH2CH3
CH CH
CH2
CH CH2
O
CH2 CH3
C
C
CCH2CH2CH2CH3
CH CH
CH3
CH
CH2 CH2
CH2
200 180 160 140 120 100 80 60 40 20 0
CCH2CH2CH2CH3
CH CH
CH3
CH
CH and CH3
unaffected
CH2 CH2
C and C=O nulled CH2
CH inverted
200 2 180 160 140 120 100 80 60 40 20 0
A) 2
B) 3
C) 4
D) 5
E) 6
Question
Of the total number of possible isomers of C7H5Cl3O they
produce two 13C NMR sets: one set respectively has 5 peaks and
the other 7 peaks in the decoupled 13C NMR spectra? Which tri-
chloro substitution pattern would produce 5 peaks?
A) 2,4,5
B) 2,3,4
C) 2,3,5
D) 2,4,6
E) 2,3,6
http://chemconnections.org/organic/Movies%20Org%20Flash/nmr-C13-flash/AADFQQZ0.swf
Question
Which compound corresponds to the 13C NMR spectrum below?
A. B
B. D
C. E
D. F
E. G
2D NMR Methods
1H
O
CH3CCH2CH2CH2CH3
1H
The COSY spectrum identifies protons that are coupled
COSY: Correlation Spectroscopy
13C
O
CH3CCH2CH2CH2CH3
1H
The HETCOR spectrum of 2-methyl-3-pentanone
indicates coupling between protons and the carbon to
which they are attached