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Experiment 4: NMR Analysis of a Constitutional Isomer

A student performed a series of experiments using hydrogen, carbon and oxygen. They made nine
different compounds all with the following elemental composition:
C 64.3%
O 28.6%
H 7.2%
and a relative molecular mass of 112.1 g mol-1. Using the following data draw and name viable
structures for compounds A to I:
Compound A

13

C NMR
H NMR

Compound B

13

C NMR
H NMR

Compound C

13

C NMR
H NMR

Compound D

13

C NMR
H NMR

Compound E

13

C NMR
H NMR

Compound F

13

C NMR
H NMR

Compound G

13

C NMR
H NMR

Compound H

13

C NMR
H NMR

Compound I

13

C NMR
H NMR

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, 97.4 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)

Note: for 1H NMR the number and letter(s) in brackets indicate how many protons are associated
with that signal and the splitting pattern; s - single, d - doublet, t - triplet, qrt - quartet, qnt - quintet
and sxt - sextet.

Figure 1 1H NMR Chemical Shifts

Figure 2 13C NMR Chemical Shifts

M
u
k
a
s
u
r
a
t