Results

Compounds
Compound A
Compound B
Compound C
Compound D
Compound E
Compound F
Compound G
Compound H
Compound I

NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
13
C NMR
1
H NMR
Table 4.8

Analysis
205.6, 189.8, 103.5, 82.8, 16.9 and 16.3
5.4 (1,s), 4.5 (1, qrt), 2.2 (3,s) and 1.4 (3,d)
194.0, 111.6, 30.1 and 5.7
2.4 (4,t), 2.2 (1, qrt) and 1.5 (3,d)
208.3 and 37.6
2.7 (8,t)
163.2, 147.0, 141.3, 121.7, 97.8 and 18.2
7.4 (1,t), 7.1 (1, qnt), 5.9 (1,d), 4.7 (2,d) and 1.9 (3,d)
164.3, 141.5, 135.5, 127.2, 97.8 and 18.2
7.3 (1, t), 6.0 (2,s), 4.7 (2,d) and 2.0 (3,s)
193.0, 104.3, 70.0, 32.3 and 21.1
11.3 (1,s), 5.5 (1,s), 2.5 (2,t), 2.4 (2,t) and 2.0 (2,qnt)
152.6, 152.1, 108.6, 106.3, 57.1 and 13.5
6.1 (1,d), 5.9 (1,d), 4.5 (2,s), 2.3 (1,s) and 2.3 (3,s)
203.8, 149.5, 145.9, 32.1, 27.3, and 14.4
6.7 (1,s), 2.4 (2,t), 2.3 (2,t) and 2.0 (3,s)
158.5, 92.6, 72.9, 21.0, 20.7 and 13.4
9.7 (1,s), 2.3 (2,t), 1.6 (2, sxt) and 1.0 (3,t)

13

C and 1H NMR analysis of compounds (A-I)

4.8

Discussion

The objective of this experiment is to identify compounds of constitutional isomer using

NMR analysis. There are 9 compounds (A-I) needed to be identified. The compounds are
constitutional isomers. The data analysis from 13C NMR and 1H NMR are given for each
compound. The constitutional isomers are made up from three different species element (C,
O, H). It is given the compounds having the following elemental composition
C 64.3%
O 28.6%
H 7.2 %
and a relative mass of 112.1 g/mol.

112.1 g/mol X %E = MWE

; let E to be the subject element

MWC = 112.1 g/mol X 64.3% = 72.08 g/mol

MWO = 112.1 g/mol X 28.6% = 32.06 g/mol
MWH = 112.1 g/mol X 7.2% = 8.07 g/mol
From the percentage and the total molecular mass we know that the compounds are made up
of 72.08 g/mol of C, 32.06 g/mol of O and 8.07 g/mol of H. It is known that the relative
atomic mass for; C is 12.011 g/mol, 15.999 g/mol and 1.008 g/mol.
NC =

72.08 g /mol
12.011 g /mol

= 6C

NO =

32.06/mol
15.999 g/mol

= 2O

NH =

8.07 g /mol
1.0888 g/mol

= 8H

From the two sets of data, we can get the ratio of the compounds to compose of C 6H8O2. In
identifying the structure of the compounds, graph of 1H NMR chemical shifts and 13C NMR
chemical shifts are used to determine and justified the structure constructed. The results are:

Compound A:

Buta-1,2-dien-1-yl acetate
13

C NMR

205.6
189.8
103.5
82.8
16.9
16.3

H NMR

Description

Description

ketone,
double bond,
double bond,
double bond,

5.4 (1,s)
4.5 (1,qrt)
2.2 (3,s)
1.4 (3,d)
sat. alkane,
sat. alkane

ester
double bond
sat. alkane
sat. alkane

13

C:

H:

Compound B:
2-methylcyclopentane-1,3-dione
13

C NMR

194.0
111.6
30.1
5.7

H NMR

Description

Description

ketone,
sat. alkane
sat. alkane

2.4 (4,t)
2.2 (1,qrt)
1.5 (3,d)
sat. alkane

sat. alkane
sat. alkane
sat. alkane

13

C:

H:

Compound C:
Cyclohexane-1,4-dione
13

C NMR

13

Description

208.3
37.6

ketone,

C:

H NMR

2.7 (8,t)
sat. alkane

Description
sat. alkane

H:

Compound D:
Ethenyl (2E)-but-2-enoate
13

C NMR

163.2
147.0
141.3
121.7
97.4
18.2
13

C:

Description
ester
double bond
double bond
double bond
double bond
sat alkane.

H NMR

7.4 (1,t)
7.1 (1,qnt)
5.9 (1,d)
4.7 (2,d)
1.9 (3,d)

Description
double bond,
double bond,
double bond,
double bond,
sat alkane.

Compound E:
Methyl-2-methylidenebut-3-enoate
13

C NMR

Description

164.3
141.5
135.5
127.2
97.8
18.2

ester
double bond
double bond
double bond
double bond,
Sat. alkane

H NMR

Description

7.3 (1,t)
6.0 (2,s)
4.7 (2,d)
2.0 (3,s)

double bond
double bond
double bond
sat. alkane

13

C:

H:

Compound F:

Cyclobutylideneacetic acid
13

C NMR

193.0
104.3
32.3
21.1
97.8
18.2

H NMR

Description

Description

carboxylic acid
double bond
sat. alkane
sat. alkane
double bond

11.3 (1,s)
5.5 (1,s)
2.5 (2,t)
2.4 (2,t)
2.0 (2,qnt)
sat. alkane

carboxylic acid
double bond
sat. alkane
sat. alkane
sat. alkane

13

C:

H:

Compound G:

(3E)-5-hydroxyhexa-3,5-dien-2-one
13

C NMR

13

H NMR

Description

Description

152.6
152.1
108.6
106.3
57.1
13.5

ketone
double bond
double bond
double bond
C-OH

6.1 (1,d)
5.9 (1,d)
4.5 (2,s)
2.3 (1,s)
2.3 (3,s)
sat. alkane

double bond
double bond
double bond
ROH
double bond

C:

H:

Compound H:

6-methyl-2,3-dihydro-4H-pyran-4-one
13

C NMR

203.8
149.5
145.9
32.1
27.3
14.4
13

C:

H:

H NMR

Description

Description

ketone,
double bond
double bond
sat. alkane

6.7 (1,s)
2.4 (2,t)
2.3 (2,t)
2.0(3,s)
sat. alkane
sat. alkane

double bond
sat. alkane
sat. alkane
sat. alkane

Compound I:

Hex-2-ynoic acid
13

C NMR

158.5
92.6
72.9
21.0
20.7
13.4
13

C:

H:

H NMR

Description

Description

carboxylic acid
triple bond
triple bond
sat. alkane

9.7 (1,s)
2.3 (2,t)
1.6 (2,sxt)
1.0 (3,t)
sat. alkane
sat. alkane

carboxylic acid
sat. alkane
sat. alkane
sat. alkane