1

H-­‐NMR  Spectroscopy  Worksheet  

Part  I  

For  each  of  the  molecular  formulas  shown  below  calculate  the  index  of  hydrogen  deficiency  (IHD).    In  
addition,  suggest  three  possible  chemical  structures  that  are  consistent  with  the  degree  of  unsaturation.  
 
 
a) C7H14O2   DBE = 1 + 7 - 14/2 = 1
 
 
 
 
b) C4H10O   DBE = 1 + 4 - 10/2 = 0
 
 
 
 
c) C9H10O   DBE = 1 + 9 - 10/2 = 5
 

d) C8H9NO3   DBE = 1 + 8 - 9/2 = 4

 
 
 
 
 
e) C4H6O2  

f) C7H10Cl2  

   
Part  II  

For  each  of  the  following  chemical  structures  a  1H-­‐NMR  spectrum  is  provided  on  the  following  3  pages.    
Match  each  compound  with  its  1H-­‐NMR  spectrum.    Draw  the  structure  above  the  corresponding  
spectrum  and  clearly  assign  the  chemical  shifts  to  the  appropriate  protons  on  the  molecule.  

   

CH2 O
CH3

CH3
O
1-pentene 3-methylbutanal
p-ethylanisole
O O
O

O O
OH
Br

butanoic acid 2-bromobutane diethyl malonate

O O

OH Br
O O

1-propanol 1-bromopropane
diethyl ethylmalonate
 1.80 1.70 1.60 1.50 1.40 1.30
3.0

2.0 2.0
2.32 2.30 2.28 2.26 2.24 2.22 2.20 1.0

            3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8          
3.0

2.0

2.0

2.20 2.10 2.00 1.90 1.80 1.70 1.60

                    3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8  

 
4.20 4.15 4.10 4.05 4.00
  3.0 3.0

  2.0

1.0
 
1.90 1.85 1.80 1.75 1.70 1.65

 
4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8
 5.9

 
1.0

 
2.0
 
9.82 9.80 9.78 9.76 9.74 9.72 9.70

  0.9

 
2.50 2.40 2.30 2.20 2.10 2.00

5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 0.4 ppm

 
3.0

 
3.0
 

 
2.0 2.0
2.0  

7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 ppm
 

 
6.0
 
4.0
2.0
 

4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 ppm

 
   3.0

  1.9
2.0 2.0
 
5.80 5.60 5.40 5.20 5.00

 
1.0
 

 
1.60 1.50 1.40 1.30 1.20 1.10 1.00 0.90 0.80

 
5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
  ppm

 
3.0
 
2.0 2.0
 

 
Offset @ 11.8 ppm broad singlet
Integration 1.0
 

3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 0.6 0.4 ppm
 

 
6.0
 

  4.0

3.0
 

  2.0

 
1.0

4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 1.0 0.8 ppm
  

Part  III  

Shown  below  are  the  structures  of  two  esters.    They  are  isomers  and  the  only  difference  between  the  
two  compounds  is  the  orientation  around  the  ester  functional  group.    We  have  provided  the  1H-­‐NMR  of  
each  ester  in  the  next  page.  

1) Match  each  compound  with  its  1H-­‐NMR.  

2) Draw  the  structure  above  the  spectrum  and  assign  the  protons  to  their  appropriate  chemical  
shifts.  

    O
O
O
O

benzyl propionate ethyl phenylacetate

 5.0

3.0
2.0

2.0

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm  
 
 
2.0
3.0

4.9

2.0

7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm  

   
Part  IV  
 
The  1H-­‐NMR  spectra  of  the  following  pages  represent  mono,  di  and  trisubstituted  aromatic  compounds.    
Also  included  are  disubstituted  compounds  as  ortho,  meta  and  para.    The  compounds  representing  each  
spectrum  are  shown  below.  
 
a) Match  each  1H-­‐NMR  spectrum  to  its  compound.  
b) Draw  the  chemical  structure  above  the  spectrum  and  indicate  the  protons  on  each  chemical  
shift.    You  do  not  have  to  assign  each  specific  peak  on  the  aromatic  region.  

 
CH3
  O C
H2C H CH3 CH3
 
Cl

 
CH3
  O2N

2-chloro-5-nitrobenzaldehyde Isobutylbenzene m-xylene

 

  OH OH OH

NO2
 

 
NO2

  NO2

o-nitrophenol m-nitrophenol p-nitrophenol

 
O
  OH

  OH

 
O
 
CH3

  o-vanillin phenol

 
 2.0 2.0
 

  1.0
1.0
  5.1

  7.30 7.20 7.10 7.00 6.90 6.80 6.70

 
7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 ppm
 

 
3.0 6.0
 

  1.0

  3.0

 
1.0 7.40 7.30 7.20 7.10 7.00 6.90 6.80 6.70

 
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
ppm
 

 
1.0 1.0
1.0
 
8.90 8.80 8.70 8.60 8.50 8.40

Offset @ 10.5 ppm singlet  

Integration 1.0
 

9.8 9.6 9.4 9.2 9.0 8.8 8.6 8.4 8.2 8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm
  

 
Offset @ 11.2 ppm broad singlet
  Integration 1.0 1.0
3.0
 
2.0
  1.0

  9.90 9.85 9.80 9.75 9.70

7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 ppm
 
6.0

 
5.0 2.0
 

  1.0

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm
 

 
Offset @ 10.6 ppm broad singlet
  Integration 1.0

  1.0 1.0 1.0 1.0

8.4 8.2 8.0 7.8 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 ppm
 
  

Offset at 10.3 ppm small broad singlet

Integration 1.0

1.0

1.0

1.0
1.0

7.80 7.60 7.40 7.20 7.00 6.80

2.0 2.0

Offset @ 10.7 ppm broad singlet

Integration 1.0

9.2 9.0 8.8 8.6 8.4 8.2 8.0 7.8 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 ppm