CHEM 242 Organic Chemistry Lab II

Lab Exercise #6
Proton NMR: Spectra Interpretation II

PART I
INSTRUCTIONS:
Label each type of proton in the structure with a letter and place the same letter over the
corresponding peak on the NMR spectrum (see example below). Some NMR spectra show
a peak hovering above the baseline. This is a magnified view of one of the actual peaks, to
allow you to see splitting more clearly.

Example:
The 1H NMR spectrum of phenol is shown below. Assign the various resonances to the
hydrogen nuclei responsible for them.

b
c

NMR data for phenol(CDCl3).

Answer:

1
1.

NMR data for 1-chlorobutane (CDCl3).

2.

NMR data for 4-methyl-2-pentanol (CDCl3).

2
3.

NMR data for trans-4-methyl-2-pentene (CDCl3)

4.

NMR data for cis-4-methyl-2-pentene (CDCl3)

3
5.

NMR data for ethyl p-aminobenzoate (CDCl3)

4
 Part II

Instructions:
Use the spectra (A-F) below to determine their structure. Assign the various resonances to
the hydrogen nuclei responsible for them.

A.

C5H12O

B.

C8H9NO

5
C.

C4H9Br

D.

C4H6O

6
 E.
300 MHz ¹H NMR
In C DC l 3
1 .2

C6H12OS
1 .1

300 MHz ¹H NMR

1 .0
In C DC l 3
1 .2
0 .9
1 .1

1 .0
0 .8
0 .9

0 .8 0 .7
0 .7

0 .6
0 .6
0 .5
0 .5
0 .4

0 .3 0 .4
0 .2

0 .1 0 .3
0 .0
0 .2
-0.1
2 .2 5 2 .0 0 1 .7 5 1 .5 0 1 .2 5 1 .0 0 0 .7 5 0 .5 0 0 .2 5 -0.0 0
© Si g ma -Al d ri c h C o .
ALL R IGHTS R ESER VED
0 .1

0 .0

-0 .1
1 5 .0 1 2 .5 1 0 .0 7 .5 5 .0 2 .5 0 .0 -2 .5 -5 .0
© Si g ma -A l d ri c h C o .
A LL R IG HTS R ESER V ED

7
F.
300 MHz ¹H NMR
In C DC l 3
1 .2

1 .1

C8H5NO 300 MHz ¹H NMR

In C DC l 3
1.2

1.1
1 .0

0 .9
1.0
0 .8
0.9

0.8 0 .7
0.7
0 .6
0.6

0.5 0 .5
0.4
0 .4
0.3

0.2 0 .3
0.1
0 .2
0.0

-0.1 0 .1
9.00 8.75 8.50 8.25 8.00 7.75 7.50 7.25 7.00
© Si gma -Al dri c h C o.
ALL R IGHTS R ESER VED
0 .0

-0.1
10 9 8 7 6 5 4 3 2 1 0
© Si g ma -A l d ri c h C o .
A LL R IG HTS R ESER V ED

8
Following are the NMR spectra of three isomeric esters with the formula C7H14O2, all derived from propanoic acid.
Provide a structure for each and assign the various resonances to the hydrogen nuclei responsible for them.