Organic-Chemical Basic Internship

(OC-GPR)

Synthesis of Orange II

Student: Armir Zogu

Assistant:Theodor Peez
 Marburg, 17 December 2017

Contents

1. Synthesis of bromoform………………………………………………………………………………… 1

2. Experiment........................................................................................................................................... 3
Experimental Procedure:……………………………………………………………………………………………4

3.Results and Discussion..................................................................................................................... 5

4.Literature............................................................................................................................................... 6
Synthesis of Orange II

1. Synthesis of Orange II

In this mechanism hydroxile group from nitric acid gets protononated and then it takes
out the electrons from the bond since its unstable, the oxygen puts its electron in the
bond with nitrogen to stabilize it.
Now Nitrogen from amino group attacks nitrogen that is triple bonded to oxygen, the
oxygen take out electrons from the bond to stabilize it self, then each step oxygen gets
protonated and nitrogen puts its electron to form bond with the other nitrogen until
oxygen is removed as H2O and nitrogen forms triple bond.

There is an electrophilic substitution in the phenyl ring, where nitrogen is bonded in para
postion to hydroxile group.Oxygen forms a double bond to stabilize carbon
After that hydrogen is removed and carbon forms double bond and makes oxygen take
out its electron from double bond.

1. Experiment

Reactants or Molecular M(g/mol) M.p H- Mol of Mass or

product formula Sentences sub. volume

Sulphanilic acid C6H7NO3S 173.19 M.P H:315,317, 0.06 10.5g

288°C 319
Na2CO3 M.P
Sodiu carbonate 106 H:319 0.025 2.65g
851°C

Hydrochloric HCl 36.5 M.P H:290,314, 10.5ml

acid -30°C 335

B-Naphthol C10H8O 144.47 M.P H:302,317, 0.05 7.2g

121°C 319,332,33
5,400,410
Experimental Procedure:

Fit a 500ml three necked flask with a magnetic stirrer, a dropping funnel and another. In
a 250 ml conical flask place 10.5g of sulphinilic acid dihydrate, 2.65g of anhydrous
sodium carbonate dissolved in 100ml of water by heating the solution until 90°C. Cool
the solution and add a solution of 3.7g sodium nitrite in 10ml of water. Put the solution
by stirring in a 600ml beaker containing 10.5ml of conc. HCl and 60g of crushed
ice.Dissolve 7,2g of a good grade of B-naphthol in 40ml of cold 10% sodium hydroxide
solution in a 600ml beaker, cool to 5°C and stir until a clear solution is formed. Stir well,
and after 10 minutes heat the mixture until all the solid has dissolved. Add 20g of
sodium chloride to decrease solubility of product and warm until it dissolves. Allow the
solution to cool into the fridge for 12 hours, after that dry the solution in 80°C.
2. Results and Discussion

The mass of material isolated in this experiment is 31.78g The product was
analyzed by IR and melting point. The melting point of the material isolated in this
experiment is: 161°C

IR: 3373.84 (s), 1119.39(s), 1006.34(s), 1032.69(s), 825.93(s), 1169.76(s), 984.23(s),

1599.9(m),1570.74(m),1552.86(m), 1520.95(w),1395.13(w),1253.96(w),
730.84(w),1253.96(w),745.34(w),421.52(w),496.84(w),566.32(w),695.2(w),
3. Literature