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Hi, can someone who is an expert in Organic Chemistry tell me if my answers are correct?

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1. How many signals are expected in the 13C—NMR spectrum for each of the following compounds? 5 signals 5 signals
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8. Propose a structure that is consistent with the following data:
Molecular
Formula
CsH13N
* TRANSMITTANCE
3086.21
1686.84
1317.35 -
1149.72
1845.55
IR
1462.23-
922. 89
2983. 12782.53
3020
1580
6H
1H-NMR
1H
4H
2H
2
PPM
13 C-NMR
200
180
160
140
120
CDS-07-466
100
60
ppm
40
20
CH3-CH2-CH-CH2-CH3
Structure
NH
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9. An unknown compound (B) has a molecular formula of C1oH120 and the following 1H—IsllVlR
spectrum. The IR spectrum of B has strong bands near 1715 cm'1 and in the range from 1600
1301450 cm“. (a) What is the index of hydrogen deficiency for compound B?
The index of hydrogen deficiency is 5. (b) How many aromatic protons are present in compound B?
The aromatic proton present in the structure are 5. (c) What is the structure of compound B? H2 H2
C TC —CH3
0 (d) How many signals are expected in the 13C-NMR spectrum for compound B? In the given structure 6 signal are expected.
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2. Propose a structure (molecular formula is C5H14) that would result in the following 1H—NMR data. 0.96 3 H30
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3. Circle the molecule that best fits each of the following 1H—NMR spectra. (a)
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The following 1H—NlVIR spectra represent three constitutional isomers with molecular
formula C5H12. Insert a structure corresponding to each spectrum. (Note: all signals appear in the range of 5 0.7 - 1.6)
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4. Butanoic acid, ethyl acetate, and 2-methylpropanoic acid are constitutional isomers of one
another. Determine which isomer gives rise to each of the following 'H-NMR spectra.
H-NMR Spectrum
Name of Isomer
o
CH 3
-C-
CH
12
1 10 9 8 7 41 ( 80m ) 5
-516.50
(113.51
106.21
98.94
9231
94 97
- 78.49
H3 C
CH3 -
OH
2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4
11
10 9
8 7 (1 ( ppm)
5 4
6 -0.97-
.OH
12
11
-1.24-
10
9
8 7
1 (8 pm ) 5 4 3
2
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5. Predict a structure for each the following 'H-NMR spectra. Insert your structure to the right of
each spectrum.
(a) C3H8O
3H
2H
CH3-CH2-CH2-OH
1H 2H
11
10 9
8
7
6
5 4 3
2
0
(b) C4H&C12
3H
CH3-CH-CH2-CH2-CI
CI
2H
2H
TF
11
10
9
8
7
6
5 4 3
2 1 0
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6. Propose a structure that is consistent with the following data:
Molecular
Formula
C4H100
1248
1367
1471-
IR
* TRANSMITTANCE
2874
2957
1041
3508
capillary film betwen salt plates
WAVENUMBERS
2020
1580
eset
Copyright 1992 680.
H-NMR
4.0
3.5
3.0
2.5
1.5
1.0 PPM
0.5
13 C-NMR
200
180
160 140 120
100
CDS-03-352
40
pom
20
O
OH
Structure
H3
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7. Propose a structure that is consistent with the following data:
Molecular
Formula
C&H8O
2922
* TRANSMITTANCE
1368
1307
IR
1217
1169 -
810-
4800
3080
2500
capillary film between salt plates WAVENUMBERS
1500
1000
Copyright 1992 680.0
1H-NMR
10 Proton NMR 9
2 PPM
13 C-NMR
200
180
160
140
120
100
80
60
CDS-03-079
40
20
O
pom
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