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Misr International University

Faculty of Pharmacy
Pharmaceutical Chemistry Department

Practical
Pharmaceutical Organic Chemistry I

PHC 111

Dr. Ibrahim Elghamry


Contents
Page
Laboratory Safety 3
Tools and glassware 6
Identification and Classification of Organic Compounds 7
Collective Prospective: A- Physical Characterizations: 8
1- Conditions 8
2- Colour 8
3- Odour 8
4- Solubility 9
5- Dry heat 11
Working Sheets 13
B- Chemical Characterizations: 16
1- Action of Soda lime 16
2- Action of 30% NaOH 17
3- Action of Concentrated H2SO4 18
4- Reaction with FeCl3 19
Working Sheets 21
Organic Compounds and Functional Groups Identification 24
1- Aliphatic hydrocarbons (Alkenes) 24
Working Sheets 26
2- Alkyl Halides 28
Working Sheets 30
3- Alcohols 33
Working Sheets 37
4- Aldehydes and Ketones 40
Working Sheets 44
5- Aliphatic Carboxylic Acids 47
A- Aliphatic Monocarboxylic Acids 47
B- Aliphatic Polycarboxylic Acids 50
Working Sheets 53
6- Salts of Aliphatic Carboxylic Acids 56
Working Sheets 57
Working Sheets for Final Practice 61
Prelab Exercise:

Read this part carefully.

Locate the emergency eye-wash station,

Safety shower and fire extinguisher in your lab.

Check your safety glasses or goggles for size and transparency.

Learn:

How to someone help and how to put out a clothing fire.

First aid procedure for acid and alkali spills on the skin.

The procedures for properly disposing of solid and liquid waste in your

lab.
Important General Rules

Know:
The safety rules of your particular lab.
The locations of emergency eye washes and safety showers.

NEVER: :!
Eat,
Drink,
Or Smoke in the lab.

Do not
Work alone.
Perform no unauthorized experiments
Distract your fellow workers;
Horseplay has no place in the lab.

Eye protection is extremely important.


Safety glasses of some type must be worn at all times.
Contact lenses should not be worn
Because reagents can get under a lens and cause damage to the eye before the lens
can be removed.
It is very difficult to remove a contact lens from the eye after a chemical splash has
occurred.
Ordinary prescription eyeglasses do not offer adequate protection.

Dress sensibly in the lab.


Wear shoes, not sandals or cloth-top sneakers.

Confine long hair and loose clothes. Do not wear shorts.

Do not use mouth suction to fill a pipette.

Wash your hands before leaving the lab.


Do not use solvent to remove chemicals from your skin.
This will only hasten the absorption of the chemical through the skin.
TOOLS & GLASSWARES
Identification and Classification
of Organic Compounds

Collective prospective

For the purpose of identification of an organic functional group as well as an


organic compound, the following scheme for laboratory work should be applied

A) Physical Characteristics:

1. Condition
2. Colour
3. Odour
4. Solubility
5. Dry heat

B) Chemical Reactions:
1. Action of soda lime (on solid only)
2. Action of 30%NaOH
3. Action of conc. H2SO4
4. Reaction with FeCl3

C) General Class Reaction and Special Tests


A) Physical characteristics:
1. Conditions:

The material is either Solid or Liquid


a) Solid:
o Powder.
o Crystalline (shiny) which may be micro or macro crystals
(e.g. needles, plates, balls) according to the size

b) Liquid:
You have to determine whether the liquid is
• True liquid or solution:
By using anhydrous copper sulphate in a watch glass then add few drops of
the compound:
♦ True liquid: the colour does not change.
♦ Solution in water: the colour changes from green to blue.
• Mobility: viscous, oily

2. Colour:

o The colour of the original sample is noted


o Compounds may show colour due to impurities or chromophoric groups
o The colour observation may help to expect the unknown compound.

3. Odour:
o Some organic compounds have characteristic odour,
(Strong smelling is avoided)
e.g. Alcoholic odour: methanol, ethanol
Bitter almond odour: benzaldehyde
Mice like odour: acetamide
Pleasant fruity odour: esters
Vinegar odour: acetic acid.
4. Solubility:

Solubility is used to indicate the nature of the organic compound & its functional
group, by trying solubility at room temperature in:
1-H2O 2- dilute NaOH 3- dilute HCl

♦Solubility Test:

1- Few amount of solid (finely powdered) or (0.2 mL) of liquid in a test tube.
2. Add 5 mL solvent (H2O, dilute NaOH or dilute HCl) shake well at room
temperature, then notice the change:

A) Compounds soluble in water:


If the compound dissolves in water, test the aqueous solution with litmus
paper and observe whether it is:
Acidic (blue→red), basic (red→blue) or neutral (no change)

For example:

1. Aqueous solution acidic to litmus paper: carboxylic acids, phenols, salts of


amines.
2. Aqueous solution basic to litmus paper: sodium or potassium salts of
carboxylic acids
3. Aqueous solution neutral to litmus paper: alcohols, aldehydes, ketones or
sugars.

B) Compounds insoluble in water and soluble in 10% NaOH:


♦ If the compound is insoluble in water, try solubility in dilute NaOH
• If the compound is soluble in 10% NaOH, and reprecipitate by
adding conc. HCl, this indicates it is acidic substance
For example: Higher aliphatic acids

Sodium carbonate test:


• This test is carried out to differentiate between strong and weak acidic
organic compounds.
• This test is carried out for compounds:
a) Soluble in water & acidic to litmus paper
b) Insoluble in water & soluble in 10% NaOH

Procedures:
1. In a test tube, with 2 mL of Sodium carbonate solution add few crystals of
the substance. (warm if necessary)
2. Note the effervescence:

• If there is effervescence and evolution of CO2 then the substance is


strong acid e.g. carboxylic acids or aniline salts
• If there is no effervescence then the substance is weak acid eg:
phenols

C) Compounds insoluble in water, dilute. NaOH and soluble


in dilute HCl
• If the compound is insoluble in dilute NaOH, try solubility in dil HCL
• If the compound is soluble in dilute HCl, and reprecipitate by 30%
NaOH, this indicates it is basic substance e.g. Aromatic amines (Aniline,
Toluidine,..)[NOT INCLUDED IN THIS COURSE]

D) Compounds insoluble in dilute. NaOH and dilute HCl:


• if the compound is insoluble in all above reagents then this compound is
neutral

5) Dry heat:
• heat a small portion of the organic compound on inverted porcelain lid or
broken glass, note carefully:
1. Inflammability:
a) Inflammable or non inflammable
(Inflammable means that when you remove the substance from the flame it will
catch fire)
b) Luminous or non luminous
c) Smoky or non smoky: e.g.
I- Unsaturated, and higher aliphatic compounds give yellow and
smoky flame
II- Lower aliphatic compounds give yellow and non-smoky flame
III- Lower alcohols: Give clear bluish flame

2. Change in appearance:
As seen (melts, blackens, charring, swelling, evaporates)
3. Change in odour:
As detected (ammonia odour, burnt sugar odour,…)
4. Change in colour:

• Sodium salts: Golden yellow flame


• Potassium salts: Violet flame
• Organic halogen compounds: Green flame
5. Residue:
Notice, if there is a residue (remaining) after ignition or not
• if the residue is present, check if the residue is
A. Metallic residue: produced from ignition of metallic
derivatives e.g. alkali salts of carboxylic acids
B. Nonmetallic residue: residue of carbon which may be
very difficult to burn off completely
Procedure:
Allow the residue to cool then add few drops of dilute HCl and
observe the effervescence which appears in case of metallic
residue.
Working Sheet
Sample 1:

Chemical Name:

Chemical Structure:

Physical Characterizations
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Working Sheet
Sample 2:

Chemical Name:

Chemical Structure:

Physical Characterizations
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Working Sheet
Sample 3:

Chemical Name:

Chemical Structure:

Physical Characterizations
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B. Chemical Characteristics:

1. Action of Soda-Lime: (On Solids only)

• Soda lime is a fused mixture of NaOH and CaO.


• Its main action is based on the action of NaOH, while CaO decompose or
dehydrate the substance.
• This test is done on solid only.

• If your compound is a liquid, this test is not done.


Procedure:

In a mortar, mix one part of the compound with three parts of soda lime,
grind and notice any change at room temperature (r.t.) first (odour or any
change in the nature of the sample).
If no odour is produced at room temperature, transfer part of the mixture into
a dry test tube and heat (CAUTION!!!!).

The action of soda lime on organic compounds involves the following reactions:
• Decarboxylation
e.g. Carboxylic acids give parent hydrocarbon.
RCOOH ⎯⎯⎯→ R-H
• Hydrolysis
e.g. Amides give ammonia odor.
R-CO-NH2 ⎯⎯⎯→ R-COONa + NH3

• Dehydration
e.g. Carbohydrates give burnt sugar odor due to the removal of water
molecules.
• Neutralization
e.g. Amine salts give free amines.
R-NH2.HCl ⎯⎯⎯→ R-NH2
Some important observations are summarized in the following table:

Observation Expected substance

Ammonia odour at r.t. Ammonium salt of carboxylic


acids
Ammonia odour on hot Amides or imide
Fishy odour at r.t. Salts of amines
Burnet sugar like odour on hot Carbohydrates and some
aliphatic hydroxyl acids and
their salts.
Hydrocarbons evolved on hot Carboxylic acids or their salts

2. Action of 30% NaOH:

The action of 30% NaOH is done on both solids & liquids.


Procedure:
30% NaOH is added directly on the compound in a test tube.
Note any reaction on cold (odor-color).
If no reaction at room temperature, then heat and observe any change.

I-Odour:
Some important observations are summarized in the following table:

Observation Expected substance

Ammonia odour at r.t. Ammonium salt of carboxylic


acids
Ammonia odour on hot Amides or imide
II-Observation of any change in:
Some important observations are summarized in the following table:

Observation Expected substance

Brown resinous material on hot Aliphatic aldehydes


Yellow solution which rapidly Polyhydroxy compounds
darkens on shaking
White emulsion at r.t. Some esters

The action of 30% NaOH on organic compounds involves the following reactions:

• Neutralization: e.g.: amine salts to give free amines.


• Reaction with NH4 salts liberates NH3.
• Polymerization: e.g. acetaldehyde, gives yellow resin.

3- Action of concentrated. H2SO4:

The action of conc. H2SO4 is done on both solids & liquids.


Concentrated. H2SO4 is added directly on the compound.
Procedure:
1- In a dry test tube, place a small amount of the compound then add 1 mL
conc.H2SO4 (CAUTION!!!!!).
2- Note the reaction first on cold then warm gently.

Precautions in dealing with conc.H2SO4 :

™ Never use large quantities of conc.H2SO4.


™ Never heat excessively (never boil).
™ Discard in running water slowly.
Some important observations are summarized in the following table:

Observation Expected substance

Evolution of carbon monoxide Formic or oxalic acids and their


salts
without blackening
Yellow colour, effervescence and Citric acid and its salts
evolution of carbon monoxide
Blackening without effervescence Polyhydroxy compounds
(resorcinol)
Rapid charring without effervescence Tartaric or tartarate
Evolution of pungent vapours without Simple carboxylic acids and their
blackening and effervescence derivatives

4- Reaction with FeCl3:

• FeCl3 is a yellow colored solution.


• This test is done on solutions only (even if the compound is a liquid)
• The observation is usually a change in color.
♦Colorations are frequently given by the reaction of FeCl3 with :

a. Acids & their salts.

b. Phenols [NOT IN THIS COURSE]

c. Amines [NOT IN THIS COURSE]

Procedure:
1- In a test tube add a small amount of the substance (as a solution) then
add three drops of ferric chloride.
2- Notice any change in color.
™ This test depends on solubility results:
NOTE: Few amount of solid is dissolved in excess amount of solvent.
Dissolve in the proper solvent
The proper solvent must:
i) Dissolve the compound completely.
ii) Not interfere with the reaction.
If the compound is neutral, basic, or weakly acidic:

If the compound is strong acid: (free acid)


It must be neutralized by preparing a neutral solution, (N.S.) as follows:

1. In a beaker, add small amount of the acid + 25mL water + red


Litmus paper (L.p.). Then add NH4OH dropwisely till the red L.p.
turns blue.
2. Boil the beaker on direct flame to evaporate excess NH3.
3. Check the absence of ammonia (notice the color of the L.p.) then
cool.
4. Take some of the prepared N.S. in a test tube then add 3drops FeCl3.
Note: When a lemon yellow color is produced, blank solution should be prepared,
to differentiate between the lemon yellow color and the yellow color of FeCl3.

Blank Experiment:
Take 3 mL H2O in a test tube, add 3 drops FeCl3 then shake.
Compare between the colour produced with the compound and the color of the
blank experiment.
Working Sheet
Sample 1:

Chemical Name:

Chemical Structure:

Physical Characterizations
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Working Sheet
Sample 2:

Chemical Name:

Chemical Structure:

Physical Characterizations
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Working Sheet
Sample 3:

Chemical Name:

Chemical Structure:

Physical Characterizations
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