Experimental

Organic
Chemistry
B.Sc. Students
Second Term

A.TA77AN
2011
www.Science-Union.com
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [1]
Synthesis of Phthalimide

1
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Materials

a) Phthalic unhydride ................... ( say 2 g )

b) Urea ................... (Xg)

Phthalic unhydride + Urea Phthalimide

1 mole 2 mole 1 mole
148 2 60 147
2 X Y

2 120
Wt. of Urea (X) = = 1.6 g
148

www.Science-Union.com
2
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [2]
Synthesis of Acetylsalicylic Acid
(Aspirin)
Equation
COOH COOH
OH O CH3
Conc. H2SO4 C
+ Ac2O
O
Salicylic acid Acetic Anhydride Aspirin
M.Wt. 138 102 M.Wt. 180
M.P. 160 oC B.P. 139 oC M.P. 135 oC
d 1.08 g/l

Mechanism [A] In the absence of tha acid

COOH O O
COOH
OH C C CH3 O
H3C O CH3
O C O C CH3
H O

COOH COOH
CH3 O
O CH3
C - CH3COOH O C O C CH3
O O H

3
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

4
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Method

- Put 5 g of Salicylic acid in a beaker.

- Add 10 ml of Ac2O .
- Add 1 ml of Conc. H2SO4 .
- Heat on the water bath for 5 min.
- Cool.
- Add 100 ml of water (help cooling and removal of acetic anhydride).
- Filter.
- Wash by water.
- Dry (air drying is the best drying way in the synthesis).
- Weigh the formed solid (this is the practical yeild weight).
- Recrystallize ( Water : Alcohol 2:1).
- Record M.P. - IR - MS - NMR.

www.Science-Union.com

5
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [3]
Synthesis of Picric Acid
Reaction
OH OH
O2N NO2
HNO3
H2SO4
NO2
Phenol Picric acid
M.Wt. 94 229
M.P. 40 - 42 oC 22 - 23 oC

Electrophilic Substitution Reaction

Mechanism

H
- H2O
H2SO4 + HO NO2 HSO4 + O NO2
H

OH OH
HSO4 NO2
NO2
H
act as E+
OH OH
NO2 NO2
and so on.

6
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Method

- Put 7.5 g of Phenol in a beaker.

- Add 20 ml of Conc. H2SO4 .
- Shake well.
- Heat on the water bath 30 min.
- Cool.
- Add 22 ml of Conc. HNO3 (portion by portion) , a brown f umes of
nitrogin oxides will evolved and the mixture turned red.
- Heat on the water bath 1 hr.
- Cool .
- Add 50 ml of water, picric acid will formed.
- Filter.
- Wash by water.
- Dry (air drying is the best drying way in the synthesis).
- Weigh the f ormed solid (this is the practical yeild weight).
- Recrystallize ( Water : Alcohol 2:1).
- Record M.P. - IR - MS - NMR.

7
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [4]
Synthesis of Phthalylglycine

8
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Method

- In a f lask place 6 g of phthalic anh. + 3 g of glycine.

- Fuse the mixture on hot plate f or 15-20 min.
- Cool.
- Add water.
- Fliter.
- Dry (air drying is the best drying way in the synthesis).
- Weigh the f ormed solid (this is the practical yeild weight).
- Recrystallize f rom Water.
- Record M.P. - IR - MS - NMR.

www.Science-Union.com
9
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [5]
Synthesis of Hippuric Acid
(Benzoylglycine)
Equation
Cl O H
C O N COOH
COOH C C
NaOH H2
H2C +
NH2

Glycine Benzyl chloride Hippuric acid

M.Wt. 75 140 179
M.P. 233 oC B.P. 197 oC 187 oC
d 1.21 g/l

Mechanism

H2 H2 OH H2
H2N C COOH H3N C COO Na H2N C COONa

O H O Cl O
H2 H H2 C
OOC C N C Cl OOC C N C Cl
H

H
O N COOH
C C
H2

10
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Method

- In a f lask dissolve 3.7 g of Glycine in 37.5 ml of 10% NaOH Soln.

- Add 7 ml of benzoylchloride (portion by portion) while strong shaking.
- Transf er the solution into a beaker containing crushed ice.
- Add Conc. HCl slowly while stirring until the soln becomes acidic (now
the solid product will f ormed).
- Filter.
- Wash by water.
- Dry (air drying is the best drying way in the synthesis).
- Weigh the f ormed solid (this is the practical yeild weight).
- Recrystallize from Water.
- Record M.P. - IR - MS - NMR.

www.Science-Union.com
11
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [5]
Synthesis of Acetanilide
Equation
NH2 H
O O N O
C
C C
+ H3C O CH3 CH3

Aniline Acetic Anhydride Acetanilide

M.Wt. 93 102 135
B.P. 184 oC 139 oC M.P. 114o C
d 1.02 g/l 1.08 g/l

Mechanism
NH2 O O
H O O
C C
+ H3C O CH3 N C O C CH3
H
CH3
OH O
H Proton Shift
N C O C CH3
CH3

H H
N OH N O
C CH3COO C + CH3COOH
CH3 CH3

12
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

www.Science-Union.com
13
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Experiment [7]
Synthesis of Dibenzalacetone

14
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Method

- Prepare an ice water bath.

- Mix 60 ml of ethanol with 80 ml of 10% NaOH Soln.
- Cool this mix in an ice water bath.
- mix 10 ml of benzaldehyde with 3.7 ml of acetone.
- Add both mixtures to each other.
- Stir for 30 min (or heat gentely for 5 min).
- Cool in an ice water bath.
- Filter.
- Dry (air drying is the best drying way in the synthesis).
- Weigh the f ormed solid (this is the practical yeild weight).
- Recrystallize f rom ethylacetate (or ethanol).
- Record M.P. - IR - MS - NMR.

15
Experimental Organic Chemistry B.Sc. Students Second Term A.TA77AN 2011

Calculations
Benzaldehyde Dibenzalacetone
2 mole 1 mole
2 106
212 g 234 g
212 g
= 203 ml
1.044 g/l
10 ml Y

10 234
Thoretical Yeild Wt. (Y) = = 11.5 g
203

Practical Yeild Wt.

Yeild % = 100
Theoretical Yeild Wt. (Y)

Best Wishes

A.TA77AN
www.Science-Union.com
16