IDENTIFICATION OF AN UNKNOWN USING DU, IR, NMR, and

MS

Provides you with the opportunity to demonstrate your grasp of Spectroscopic (IR, NMR) and
Spectrometric (MS) data in conjunction with degrees of unsaturation (DU) in the identification of
Organic Substances

DEGREES OF UNSATURATION

1. Calculate Degrees of unsaturation for an unknown of

molecular formula C4H8O2
Degree of unsaturation= C + N/2 – H/2 – X/2 + 1

= 4 - 8/2 + 1

=1

2. On the basis of your calculation draw the possible type and

the number of functional groups that might be present in
your molecule
Carboxylic acid

Easter
 INFRARED SPECTROSCOPY

1. On the basis of the infrared spectrum draw all the functional groups present in the
molecule along with their respective wavenumbers

Functional Group Wavenumber

- …Alkane…………………. ……2980 …………..

- …carbonyl group………………….. …1750………………

 - …ether………………….. ……1200……………..

2. On the basis of the infrared spectrum draw all the oxygen-containing functional
groups (along with their respective wavenumbers) that are NOT present in the
molecule

Functional Group Wavenumber

- Alcohol……………………. …3200-3400……………..

- …carboxlic acid………………….. …3500………………

- …ester………………….. …1735………………..

DEGREES OF UNSATURATION AND INFRARED

SPECTROSCOPY

 One degree of unsaturation is equivalent to 1 ring or 1 double bond (1 ππ bond).

 Two degrees of unsaturation is equivalent to 2 double bonds, 1 ring and 1 double bond, 2 rings,
or 1 triple bond (2 ππ bonds).

Remember, the degrees of unsaturation only gives the sum of double bonds, triple bonds and/or rings.
For instance, a degree of unsaturation of 3 can contain 3 rings, 2 rings+1 double bond, 1 ring+2 double
bonds, 1 ring+1 triple bond, 1 double bond+1 triple bond, or 3 double bonds.
NMR (Nuclear Magnetic Resonance) DATA

1. Based on the number of signals how many TYPES of hydrogens are there in this molecule?
Starting from The 0 ppm ( reference for TMS upfield) and going downfield (towards 11 ppm) list
the various types along with their chemical shifts. Describe the splitting Pattern (singlet, doublet,
triplet, quartet,…)

TYPE Chemical Shift Splitting Pattern

- A ……1ppm…………..
triplet…………………….

- B 2.3ppm…………………
quartet……………………..
 - C 3.6ppm…………………..
singlet…………........

2. Integration
Fill in the table below with the missing information

TYPE Chemical Shift Splitting Pattern Integration

- A
- 2.30ppm…… doublet of doblet………… 3 Hydrogens

- B 2.3ppm…. doublet …… 2 Hydrogens

- C …1.2ppm……… quartet……… 3 Hydrogens

PUTTING FRAGMENTS TOGETHER

1. On the basis of the Integration Draw fragments A, B, and C

FRAGMENT A
 FRAGMENT B

FRAGMENT C

singlet

Have you made use so far of all the atoms provided in the molecular formula?
If not draw the remaining atom(s) with all its (their) bonds and lone pairs (if there are)

The first feature assures that each compound gives a single sharp resonance signal. The second allows
the pure (neat) substance to be poured into a sample tube and examined in a nmr spectrometer. In
order to take the nmr spectra of a solid, it is usually necessary to dissolve it in a suitable solvent. Early
studies used carbon tetrachloride for this purpose, since it has no hydrogen that could introduce an
interfering signal. Unfortunately, CCl4 is a poor solvent for many polar compounds and is also toxic.
Deuterium labeled compounds, such as deuterium oxide (D2O), chloroform-d (DCCl3), benzene-d6
(C6D6), acetone-d6 (CD3COCD3) and DMSO-d6 (CD3SOCD3) are now widely used as nmr solvents.
Since the deuterium isotope of hydrogen has a different magnetic moment and spin, it is invisible in a
spectrometer tuned to protons.

ASSEMBLE ALL YOUR FRAGMENTS IN A MANNER THAT IS CONSISTENT WITH THE

VALENCY OF EACH ATOM AND THE DATA PROVIDED. DRAW A REASONABLE
STRUCTURE OF YOUR UNKNOWN

MASS SPECTRUM OF YOUR UNKNOWN

a. Identify the molecular Ion. Does it support your proposed structure? Explain

The unknown compound is C5H12O

b. Identify one fragment in the mass spectrum of your unknown? Does it

support your proposed structure? Explain

The fragment of 57 is base peak which is more stable. The other fragment peak of
29 is also strong indicating that it is aliphatic alcohol.