Perales, Kent Benedict B.

2CHEM1 May 15, 2020

Group 9

Virtual Lab for Methyl Orange

Q1) Show the schematic diagram of the methyl orange synthesis from the
video and a schematic diagram of the one present in your lab manual and
compare them as to the differences in the methods.

Schematic diagram of Methyl Orange (video)

Part 1:

Part 2:
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

Schematic diagram of Methyl Orange (Lab Manual)

Part 1:
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

Part 2:
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

Aside from the differences in the weight and volume of the reagents used in both
experiments, it was observed that in our lab manual’s procedure, it required a gravity-
filter on the diazotization of sulfanilic acid. Furthermore, it was also seen that in the lab
manual that the synthesis of methyl orange needed to be vacuum filtered twice in the
procedure, wherein the first one was for the purification of the solution and the second
one was for the recovery of the final product, compared to the procedure in the video
which only required filtration once.
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9
Q2) Show the reaction mechanism of methyl orange synthesis.

Step 1:

Step 2:

Step 3:

Q3) Give at least 2 more azo dyes. Indicate the source of the diazo
compound and the source of the coupled compound. Also indicate the
colors at acidic and basic solutions.

Other azo dyes include Acid Orange 5 and Acid Orange 7. For Acid Orange 5 and Acid
Orange 7, their diazo compound is sulfanilic acid. The source of the coupled compound
in Acid Orange 5 is diphenylamine. The source of the coupled compound in Acid
Orange 7 is β-naphthol. The color of Acid Orange 5 in acid is red (at around pH less
than 1.4). The color of Acid Orange 7 in acid is amber (at around pH less than 7.4). The
color of Acid Orange 5 in the basic solution is yellow (at around pH greater than 3.2).
The color of Acid Orange 7 in the basic solution is red (at around pH greater than 11.8).

Q4) Give practical, industrial or commercial applications of azo dyes.

Azo dyes are utilized in dyeing textile fibers (like cotton, silk, wool, viscose) and
synthetic fibers. These dyes are also used in the fields of pharmacy, plastics, hypnotic
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9
medicine, living cells cancer and pharmacological activities, biological in high tech
applications, thermal transfer printers, and fuel cells.

Q5) Show the UV, NMR, IR and MS spectra of methyl orange and assign
important peaks just as you did during the prelims.

UV-Vis Spectrum of Methyl Orange

The graph above shows the UV-Vis spectrum of methyl orange, indicating two
absorption peaks at its maximum (lambda max). The first peak appeared at 275 nm and
the second peak, which is the tallest peak, appeared at 500 nm.

NMR Spectrum
a. 1H NMR Spectrum
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

The proton NMR spectrum shown above represents methyl orange. The spectrum
proved that there are protons attached in aromatic compounds and aliphatic
compounds. A tall peak at 3 ppm (shielded) appeared due to the (CH 3)2N- group. Next,
two small peaks, which are in the downfield direction, appeared at around 7 ppm due to
the H atoms attached on the two carbons of the benzene ring near the tertiary nitrogen.
Two peaks are found further in the downfield direction, at around 7.85 ppm due to the H
atoms attached on the other two carbons (closer to the electronegative atoms) of the
benzene ring near the N=N bond. Finally, four peaks are located on the farthest left of
the spectrum (the most deshielded) due to the H atoms attached on four carbon atoms,
which are near the electronegative atoms (oxygen atom and sulfur atom).

13
b. C NMR Spectrum
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

In the spectrum above, it can be observed that there are nine peaks, which means there
are nine different types of carbon atoms in methyl orange. The first peak can be found
at around 41.3 ppm due to the two CH 3 groups attached on the tertiary nitrogen, having
the same environment. The next peak can be located at around 111.7 ppm due to the
two carbons on the benzene ring near the tertiary nitrogen. A peak at 124 ppm can be
spotted on the spectrum due to the two carbon atoms on the benzene ring near the
N=N bond and SO3 group. Then, another peak appeared at 125.1 ppm due to the two
carbon atoms on the benzene ring near the N=N bond and the tertiary nitrogen. The fifth
peak can be seen at 128.6 ppm due to the two carbon atoms on the benzene ring near
the SO3 group. The sixth peak can be seen at 144.8 ppm due to the tertiary carbon
attached on the N=N bond and the benzene ring that is attached on the tertiary
nitrogen. The seventh peak can be found at 147.2 ppm due to the tertiary carbon that is
attached to the SO3 group. The eight peak is located at 153.3 ppm due to the tertiary
carbon that is attached to the tertiary nitrogen atom. The ninth peak is spotted at 157.7
ppm due to the tertiary carbon that is attached to the N=N bond and the benzene ring
that is attached to the SO3 group.

IR Spectrum
Perales, Kent Benedict B. 2CHEM1 May 15, 2020
Group 9

In the IR spectrum shown above, it can be seen that there is a broad absorption that is
close to 3400 cm-1. There is an absorption peak in between 1300 to 1400 cm -1 (S=O
stretching). Another absorption peak can be seen at 1600 cm -1 (N=N stretching). The
absorption peak of the C=C stretching can be spotted at 1510 cm -1. Between 1000 to
1100 cm-1, the peak of C-N is displayed. Lastly, the peaks of C-S stretching can be
spotted between 500 to 700 cm-1.

Mass Spectrum

The spectrum above shows the MS analysis of methyl orange. Both spectra show the
base peak of methyl orange, which is at m/z = 155. The base peak is the most abundant
and tallest peak that is displayed in any mass spectrum. The shortest peak is called
M+1 peak. In spectrum A, the M+1 peak is at m/z = 195. In spectrum B, the M+1 peak is
at m/z = 210. The rest of the peaks show the compound’s molecular weight fragments.