Organic Compounds Preparations Laboratory

(CY-4701)

Prof. Bimalendu Adhikari

Department of Chemistry
NIT, Rourkela
Course objectives:

This course is designed to get the experience in synthetic organic chemistry by synthesizing small organic
compounds and characterizing them.

Course materials:
1. B. Mahapatra, A. Ghoshal, A. K. Nad, An Advanced Course in Practical Chemistry, NEW CENTRAL BOOK AGENCY, 2011
2. V. K. Ahluwali, R. Aggarwal, Comprehensive Practical Organic Chemistry, University Press , 2000
3. D. S. Gupta, Experimental Organic Chemistry, Qualitative & Quantitative, TATA MCGRAW HILL , 2004
4. A. Ault, Techniques & Experiments for Organic Chemistry, University Science Book , 1998.
Common laboratory glassware and apparatus
 Common laboratory glassware and apparatus for organic synthesis

Buchner funnel

Magnetic stirrer Magnetic bid

Sintered funnel

Guard tube or drying tube

Heating mantle
Fume hood
Weighing balance

Separatory funnel Hot air oven

pressure equalising dropping funnel
 Rotary evaporator

Distillation apparatus

Magnetic
stirrer
Reflux set up

MP determining apparatus

Vacuum filtration set up Nitrogen atmosphere reaction set up

Dropping funnel Column chromatography
Personal Protective Equipment (Basic Rules)

Safety Goggles Lab Coat Closed toed Shoes

Open toed High heals

No Food/Drink in the Lab No lab glassware as
drinks containers

Use Pipette Bulb

Basic requirements for laboratory class

1. Labcoat
2. Goggles
3. Two lab records
a) Rough record
b) Fair record for evaluation
List of experiments

1. Oxidation of p-nitrotoluene using potassium dichromate

2. Benzohydrol from benzophenone (reduction)
3 . Selective reduction of p-nitroacetophenone (NaBH4/MeOH or ethanol)
4. Benzoin condensation
5. Nitric Acid Oxidation of Benzoin
6. Benzilic Acid Rearrangement
7. Synthesis of 1,1’ -Ferrocenedicarboxylic Acid
a) Synthesis of 1,1’ -Diacetylferrocene
b) Synthesis of 1,1’ -Ferrocenedicarboxylic Acid
8. Synthesis of Boc-Phe-Phe-OMe
a)Protection of N-terminal of Phenylalanine
b)Protection of C-terminal of phenylalanine by methyl groups
c) amide coupling reaction
9. Reimer–Tiemann reaction
10. Indigo from o-nitrobenzaldehyde
11. Fries rearrangement
12. Skarup synthesis
13. Fisher-indole synthesis
Evaluation process

1. Continuous evaluation 60 marks

Performance in carrying out the experiments, record writing and presentation of experimental data

2. Viva-voce (20 marks)

3. Teacher’s assessment 20 marks

(Punctuality, Response in the laboratory class)

Record writing
1. Rough record
Write down all the experiments in the rough record
After every experiment, write-down the experimental data
Get it checked and signed from me or the TA

2. Fair record for evaluation

Aim and objective
Brief theory
Experimental procedure
Results
Important observations
 Synthesis of Indigo

i) On a watch glass, weigh 1.0 g of 2-nitrobenzaldehyde and transfer it to a 100 mL beaker.

ii) Pour 20 mL acetone into the beaker.
iii) Dilute the solution with 35 mL of deionised water.
iv) Add 5 mL of 2 M sodium hydroxide slowly (with stirring) into the beaker containing the mixture.
v) Upon addition of NaOH, the solution immediately turns a deep yellow, then darker and within 20
sec a dark blue precipitate of indigo appears.
vi) Continue to stir the mixture for 5 min.
vii) Collect the dark-blue precipitate by suction filtration.
viii) Wash the precipitate by deionised water until the washings becomes colourless, then with 20 mL
of ethanol.
Mechanism: