organic chemistry

1. Synthesis of Dye para Red from Aniline
Via a Multi step sequence
Step 1:preparation of acetanilide
prepared by :
Aras Jabar
Shaxawan Rahim & Tishko Mhamad
University of slemani
School of science
Chemistry department

2. Content
• Introduction
• Reactions
• Mechanism
• I.R spectrum
• NMR 1H Estimation
• Property
• Uses
• Toxicology

3. introduction
• Para Red is prepared by diazotisation of para-nitroaniline at
ice-cold temperatures, followed by coupling with β-naphthol
• Chemical formula:C16H11N3O3
• Molar mass: 293.28gm/mol
• Appearance: Red solid
• Melting point: 248 to 252 °C

4. Reaction of synthesis Azo Dye para red
Nitric acid will react with
NH2 to form a salt or it
will oxidise the NH2 to
NO2

5. Synthesis of acetanalide

6. Mechanism of acetylation reaction:

7. Mechanism of acetylation reaction by
using acid catalyst:

8. I.R spectrum
IR for reactant(aniline) IR for product(Acetanilide)

9. NMR 1H Estimation

10. NMR 1H Estimation

11. Chemical and physical properties of
acetanilide
Appearance: It is a white solid with a flaky appearance.
Odor: This is an odorless compound.
Solubility: Acetanilide is a little soluble in water. It is also
soluble in diethyl ether, ethanol, benzene and acetone.
Molecular Weight: Its molecular weight is 135.17 g/mol.
Melting Point: It has a melting point of 114.3 °C.
Boiling Point: The boiling point for this substance is 304
°C.
Density: The density of Acetanilide is 1.219 g/ cm3.
Specific Gravity: It has a specific gravity of 1.214.

12. Uses
• It has application as an inhibitor in hydrogen peroxide.
• This compound is also used for stabilizing cellulose ester
varnishes.
• It is applied in the intermediation in accelerator synthesis of
rubber.
• This organic compound is used for manufacturing 4-
acetamidobenzenesulfonyl chloride which is one of the key
ingredients for producing sulfa drugs.
• This compound is used as a precursor for synthesizing
pharmaceuticals like penicillin.
• It was experimentally used as a photographic developer in the
19th century.

13. Toxicology
Direct skin and eye contact will result in severe
irritation. It can cause skin allergies and
irritation of the respiratory tract. More serious
effects may include blood abnormalities. This
organic powder targets different human
organs including blood, central nervous
system, kidney and skin

14. procedure:

15. Thank you for
listening