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How many unique 1H NMR and 13C NMR signals exist for the following compounds?

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Concepts and reason

There are two types of nuclear magnetic resonance spectroscopy:

1H NMR

13C NMR

• Both 1H NMR and 13C NMR gives the information about nonequivalent protons or nonequivalent carbons present in the structure.

• The resonance frequency is observed with reference to the standard compound (0 ppm) is represented as chemical shift.

• When the protons or carbons have same environment, same chemical shift value is observed and the chemical shift value is measured in ppm.

Fundamentals

The protons with same environment:

1.29
42
fo
0.90 H30
CH30.90
CH3
0.96

In the above structure, all the 6 carbons are attached to protons but only 4 signals are observed in 1H NMR because the right and left side of the protons have same environment. Therefore, those protons shows same chemical shift.

O
11.6 H3c
CH3 11.6
CH3
20.4

In the above structure, there are 6 carbons present but only 4 signals are observed in 13C NMR because, the right and left side of the carbons have same environment. Therefore, those carbons show same chemical shift.

1H NMR:

7.26
7.26 H
H726
7.28H
H7.26
7.26

13C NMR:

128.5
128.5Hс
сн 128.5
128.5 НС
сH 128.5
й
128.5

1H NMR:

7.06 H
H7.06
7.14H
H7.14
7.04

13C NMR:

CH3
138.40
129.0 HC
CH 129.0
128.6HC
CH 128.6
125.7

1H NMR:

2.34
CH3
7.34 H
CH,234
7.14H
H7 34
7.14

13C NMR:

18.8
CH3
136.8C
130.3 HC
CH2 18.8
C136.8
125.6 HC
CH 130.3
125.6

1H NMR:

CH3
7.04H
-H735
743 H
CH32,34
7.04

13C NMR:

CH
138.30
126.0 HC
CH 130.9
128.5HC
C
138.3
CH3 21.6
126.0

1H NMR:

7.11H
7.11H
CH3
2.34

13C NMR:

CH3
135.4C
128.9 HC
CH 128.9
128.9 HC
Z CH 128.9
128
1354
CH3
21.3

Ans:

The unique 1H NMR and 13C NMR signals shows for the given compounds are indicated below each structure.

H NMR = 1 signal
13C NMR = 1 signal
H NMR = 4 signals
13C NMR = 5 signals
H NMR = 3 signals
C NMR = 4 signals
H NMR = 4 s

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