Deduce the structure of a compound with molecular formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: Proton NMR 10 Chemical Shift (ppm) Carbon NMR 128.8- 128.4 126.8 35.8 30.7 179.9 140.4 180 160 140 120 100 80 60 40 20

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Deduce the structure of C9H10O2 and determine the structure of an OH.
TABLE 16.2 CHEMICAL SHIFTS FOR PROTONS IN DIFFERENT ELECTRONIC ENVIRONMENTS
TYPE OF PROTON
CHEMICAL
TYPE OF PROTON
CHEMICAL
SHIFT (6)
SHIFT (6)
Deduce the structure of a compound with molecular
Alkyl halide
Methyl
R-CH3
0.9
2-4
formula C,H1002 that produces the following 'H NMR spectrum
and 13C NMR spectrum:
R-C-X
Mathylene
1.2
Alcohol
R-0-H
2-5
CH2
Proton NMR
Methine
1.7
Vinylic
4.5-6.5
-CH
Allylic
-2
Aryl
6.5–8
Alkynyl
R-=-H
~2.5
Aldehyde
- 10
10
H.
Chemical Shift (ppm)
Aromatic
~2.5
Carboxylic
acid
12
methyl
-CH3
Carbon NMR
128.8-
128.4
TABLE 16.3
MULTIPLICITY INDICATES
NUMBER OF
NEIGHBORING PROTONS
NUMBER OF NEIGHBORS
MULTIPLICITY
RELATIVE INTENSITIES
126.8
35.8-
-30.7
140.4 –
OF INDIVIDUAL PEAKS
179.9
1
Doublet
1:1
180
160
140
120
100
80
60
40
20
Triplet
1:2:1
Chemical Shift (ppm)
1:3:3:1
Quartet
Quintet
1:4: 6:4:1
Sextet
1:5:10:10:5:1
Septet
1:6:15:20:15:6:1
Determine the structure of an alcohol with molecular
formula CgH14O that exhibits the following DEPT-135 spectrum:
-C=C-
C-N
C-o
sp'-hybridized
carbon atoms.
p-hylridized carbon
atoms (methyl,
sp>-hybridized carbon methylene, and
methine groups).
Carbon atoms of
p-hybridized carbon
carbonyl groups. These
carbon atoms are highly
deshicldod.
atoms as well as
DEPT-135
atoms that are
deshielded by
electronegative atoms.
70
60
40
30
20
10
220
150
100
50
O ppm
Chemical Shift (ppm)
FIGURE 16.22
The general location of signals produced by different types of carbon atoms.
TABLE 16.4 SIGNAL PATTERNS FOR DEPT 13c
SPECTROSCOPY
CH,
CH2
CH
BROADBAND
DECOUPLED
DEPT -90
|
DEPT -135
Transcribed Image Text:TABLE 16.2 CHEMICAL SHIFTS FOR PROTONS IN DIFFERENT ELECTRONIC ENVIRONMENTS TYPE OF PROTON CHEMICAL TYPE OF PROTON CHEMICAL SHIFT (6) SHIFT (6) Deduce the structure of a compound with molecular Alkyl halide Methyl R-CH3 0.9 2-4 formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: R-C-X Mathylene 1.2 Alcohol R-0-H 2-5 CH2 Proton NMR Methine 1.7 Vinylic 4.5-6.5 -CH Allylic -2 Aryl 6.5–8 Alkynyl R-=-H ~2.5 Aldehyde - 10 10 H. Chemical Shift (ppm) Aromatic ~2.5 Carboxylic acid 12 methyl -CH3 Carbon NMR 128.8- 128.4 TABLE 16.3 MULTIPLICITY INDICATES NUMBER OF NEIGHBORING PROTONS NUMBER OF NEIGHBORS MULTIPLICITY RELATIVE INTENSITIES 126.8 35.8- -30.7 140.4 – OF INDIVIDUAL PEAKS 179.9 1 Doublet 1:1 180 160 140 120 100 80 60 40 20 Triplet 1:2:1 Chemical Shift (ppm) 1:3:3:1 Quartet Quintet 1:4: 6:4:1 Sextet 1:5:10:10:5:1 Septet 1:6:15:20:15:6:1 Determine the structure of an alcohol with molecular formula CgH14O that exhibits the following DEPT-135 spectrum: -C=C- C-N C-o sp'-hybridized carbon atoms. p-hylridized carbon atoms (methyl, sp>-hybridized carbon methylene, and methine groups). Carbon atoms of p-hybridized carbon carbonyl groups. These carbon atoms are highly deshicldod. atoms as well as DEPT-135 atoms that are deshielded by electronegative atoms. 70 60 40 30 20 10 220 150 100 50 O ppm Chemical Shift (ppm) FIGURE 16.22 The general location of signals produced by different types of carbon atoms. TABLE 16.4 SIGNAL PATTERNS FOR DEPT 13c SPECTROSCOPY CH, CH2 CH BROADBAND DECOUPLED DEPT -90 | DEPT -135
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