Experiment 5: Qualitative Analysis

Name: Yashika Patil

November 22, 2014

Lab TA: Patrick Harrington, Alice Qin

Lab: Friday, 2 pm, Hutch 125

Introduction: In this experiment, qualitative tests and analysis of IR, NMR and mass spectra were
done to identify the two unknown liquids. First step of the process was to identify which one of
the two unknown liquids was an organohalide and which one the alcohol using the IR spectra.
The second step of the process included various qualitative tests like the Silver nitrate test,
Chromic acid test, etc., to identify the organohalide and the alcohol. The IR, NMR and mass
spectra were analyzed to find their structure and composition.
Data:
Test
Observed Boiling Range

Unknown #495
91-92oC
No reaction

Silver Nitrate test

NaI in Acetone test

N/A
No reaction within the first 5
minutes. Reaction occurred on
heating.

Lucas test

N/A

Chromic Acid test

N/A

Bromine in CCl4

No discoloration

Permanganate test

The color remained purple.

IR spectra attached.
NMR spectra attached.
Mass spectrum attached.
Results and Discussion:

Unknown #995
145-146oC

N/A
Layers did not form
immediately, but formed within
5 minutes. The color changed
from yellow to orange within 15
minutes.
An opaque greyish-green
solution formed immediately.
Slow dissipation of color which
eventually led to the solution
turning colorless.
The color of the solution slowly
changed from purple to brown.

Inference from the tests:

Test
Silver Nitrate test
NaI in Acetone test
Lucas test
Chromic Acid test
Bromine in CCl4
Permanganate test

Unknown #495
1o
1o or 2o organochloride
N/A
N/A
Saturated
Saturated

Unknown #995
N/A
N/A
o
2 alcohol
o
1 or 2o alcohol
Unsaturated
Unsaturated

Alcohol- Unknown #995

Observed boiling range- 145-146 oC
NMR AnalysisElements
C
H
O

% Composition
76.24
11.18
12.06

Molar weight
12.01
1.008
16.00

No. of moles
8.45
14.79
0.75

Simplest ratio
8
14
1

Molecular formula- C8H14O

Degree of unsaturation- 2

Chemical
shifts
Splitting
pattern
Normalized
integration

Peak A
2.5

Peak B
2.0

Peak C
1.9

Peak D
1.6

Peak E
1.5

Peak F

Singlet

Multiplet

Doublet

Doublet

Singlet

Triplet

1.0

Structure: 4-ethyl-1-hexyn-3-ol
Upon analyzing the IR spectra, there was a broad O-H absorption at 3394 cm-1, confirming that
the compound was an alcohol. It was also supported by the presence of absorptions at 1261 cm-1
and 1153 cm-1, which represents a C-O bond. The terminal C-C triple bond is supposed by
absorption at 3309 cm-1.
Electronic searching in an online organic compounds database from the library resources,
Organic Compounds Database produced no compounds. Searching the Combined Chemical

Dictionary produced 2 compounds but neither was an alcohol. The compound was predicted
from the SDBS Information by comparing the given data to the online IR and NMR spectra. The
closest match was 4-ethyl-1-hexyn-3-ol.
Thus the compound was identified to be 4-ethyl-1-hexyn-3-ol.
Literature boiling point: 160oC
The compound may have had a few impurities, which caused the observed boiling point to be 15o
lower than the literature b.p. This could also be because the identification of the compound may
be incorrect since no compound in the Library Resources matched closely with the experimental
observations. The tests for unsaturation showed results (Bromine test turned the brown solution
colorless and the Permanganate turned the solution from purple to brown) after 15-20 minutes
while they were expected to show the results within the first 5 minutes. This indicated that the
compound may be unsaturated. A very weak absorption is seen on the IR near 2150 cm-1 which
supposed the unsaturation. The degree of unsaturation for the compound is 2, also indicating that
that the molecule is unsaturated.
Organohalide- Unknown #495
Observed boiling range- 91-92oC
NMR AnalysisElements
C
H
Cl

% Composition
56.34
10.40
33.26

Molar weight
12.01
1.008
35.5

No. of moles
4.69
10.32
0.94

Simplest ratio
5
11
1

Peak A

Peak B

Peak C

Peak D

Chemical shifts

3.6

1.8

1.7

1.0

Splitting pattern

Triplet

Sextet

Quintet

Triplet

Normalized
integration

Molecular formula- C5H11O

Degree of unsaturation- 0

Structure: 1-chloropentane
Upon analyzing the IR spectra, the only major peak found was near 2960 cm-1, implying the
presence of alkyl C-H bonds. Several weak peaks wree found in 1300-1150 cm-1region, which is

usually indicative of the C-H bonds of the terminal alkyl halide. Also, the fingerprint region
demonstrates a peak 725 cm-1 which possibly indicates a C-Cl bond.
The color of the bromine and permanganate solutions stayed the same after having left the testtubes at rest indicating saturation. Also, the degree of unsaturation for the compound is 0,
indicating that that the molecule is saturated. The NaI and Silver Nitrate tests indicate the the
compound is primary.
Electronic searching in an online organic compounds database from the library resources
(http://www.colby.edu/chemistry/cmp/cmp.html) produced seven compound but neither was a
primary compound. Since the experiments showed that the compound was primary, the only
possible compound was 1-chloropentane. The literature boiling point was not very close to that
observed. However all the other experimental evidence supported this structural formular.
Thus the compound was identified to be 1-chloropentane.
Literature boiling point: 108 oC
The discrepancy in the boiling points may have arisen from contamination of the reagents.
The mass peak corresponding to the molar mass of 1-chloropentane (106 g/mol) is the last one
which is at 105. The fragments are represented the other peaks.
Conclusion: The two solutions were identified as 4-ethyl-1-hexyn-3-ol and 1-chloropentane
using various qualitative tests and analysis of IR and NMR spectra. Although some of the
literature data fails to match the experimental data, the closest matches were found and the
structure of the molecules predicted.