ORGANIC CHEMISTRY Second term 2021

2 Welcome back
 New Practical Exam Paper

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 PAPER EXAM TITLES
Physical properties: (State, Odor, Color, Dry ignition)

Solubility & Miscibility : (In 4 solvents)

General Test
Special Test

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Practical Marks Last
Practical exam Assignment

= 15 = 6
Year (25)
Book
= 4

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LAB SAFETY
Always replace the lids and caps on reagent bottles.
LAB SAFETY
Do Not return excess chemicals to the original container.
LAB SAFETY
Wash your hands and your lab bench after each experiment.
STATE
The simple observation as to whether the material is liquid or solid is a important
first guide for identification of the unknown compound.

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ODOR:
Many procedures suggest that the odor of the
compound should be noted. This practice is
strongly discouraged due to likely toxicity of
the unknown .
Many materials have disagreeable odors at
the very least. Smelling the sample must be
avoided, while any odor noticeable during
handling should not be ignored.

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SOLUBILITY / MISCIBILITY
Amount of material required: it is convenient to employ an arbitrary ratio of 0.10 g
of solid or 0.50 ml of liquid for 3 ml of solvent.
Solvents used are: Water, HCl, NaOH & Na2CO3.

Soluble Insoluble Miscible Immiscible 10

DRY IGNITION TEST
DRY IGNITION TEST
Heat a very small amount of material on the tip of a spatula in a flame lead to
Result of burn Type of compound
)on flame or powder(
Luminous sooty flame + powder charring  Aromatic compound
Blue flame + powder charring  Aliphatic compound
Residue remaining after burn and colorify the  Metal salt compound
flame depend on the metal for example : (Na &
K)
Ammonium odor  Ammonia containing
compound

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ALCOHOLS
R-OH

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OXIDATION OF ALCOHOLS

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 ALCOHOLS
(1. METHANOL)
Compound Class Structure formula

Methanol Alcohol

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 METHANOL
State Liquid

Color Colorless

Odor Alcoholic odor

Dry Ignition -ve

Volatile
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 METHANOL

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Few sample with

a lot of liquid

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 Methanol

General tests Dichromate test give green color

Estrification test give winter green odor

Special tests

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 1. DICHROMATE TEST
Primary alcohols (RCH2OH) are oxidized to aldehydes and then to acids.
Secondary alcohols (R2CHOH) are oxidized to ketones. Tertiary alcohols
(R3COH) will not oxidize with potassium dichromate.

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 1. DICHROMATE TEST

1ml of alcohol + 1 ml of a solution of potassium

dichromate in sulphuric acid and warm gently
gives (direct flame) green color

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POTASSIUM DICHROMATE
TEST Green color Result (+ve)
It is oxidation test so can oxidize sample and gives Cr+3
(green color) so,
 It is positive with
 alcohols (primary/secondary) Comment
 Aldehydes
 It is negative with
 3ry alcohols
 Ketones
 Acids
 Others
 Examples with
Potassium dichromate test
ve examples - ve examples+
2. ESTRIFICATION TEST

wintergreen odor

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 2. ESTRIFICATION TEST
1 ml of methanol + 0.5 g salicylic acid + 1 ml of conc. Sulfuric acid on the wall then
mix and warm gently in WB for 5 min to give wintergreen odor

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ESTERIFICATION TEST
Volatile Characteristic Odor Result (+ve)
It is reaction between alcohol & acid to form volatile
characteristic odor ester so,
 It is positive with
 alcohols
 Acids Comment
 It is negative with
 Aldehydes
 Ketones
 Others
 Examples with
Estrification test
ve examples - ve examples+
 METHANOL
State Liquid

Color Colorless

Odor Alcoholic Odor

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Dry Ignition - ve

General tests Dichromate test give green color

Special tests Estrification test give winter green odor

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 ALCOHOLS
(2. ETHANOL)
Compound Class Structure formula

Ethanol Alcohol

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 ETHANOL
State Liquid

Color Colorless

Odor Alcoholic odor

Dry Ignition -ve

Volatile
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 ETHANOL

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Few sample with

a lot of liquid

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 Ethanol

General tests Dichromate test give green color

• Iodoform test give yellow Crystal

Special tests
• Estrification test give rotten apple odor

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 DICHROMATE TEST
Primary alcohols (RCH2OH) are oxidized to aldehydes and then to acids.
Secondary alcohols (R2CHOH) are oxidized to ketones. Tertiary alcohols
(R3COH) will not oxidize with potassium dichromate.

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 1. DICHROMATE TEST

1ml of alcohol + 1 ml of a solution of

potassium dichromate in sulphuric acid and
warm gently gives green color

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2. ESTRIFICATION TEST

rotten apple odor

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 2. ESTRIFICATION TEST
1 ml of Ethanol + 1ml acetic acid + 1 ml of conc. Sulfuric acid on the wall then mix
and warm gently in WB for 5 min to give rotten apple odor

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 3. IODOFORM TEST
Alcohols only containing the group give the iodoform reaction such as
Ethanol and Isopropanol.

 Ethanol  Isopropanol

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 3. IODOFORM TEST
Alcohols only containing the group give the iodoform reaction such as
Ethanol and Isopropanol.

Methanol X Glycerol X

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 3. IODOFORM TEST
Alcohols only containing the group give the iodoform reaction such as
ethanol and isopropanol.

Weak
oxidizing agent

Protons
elimination

Yellow
Hydrolysis crystal
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 3. IODOFORM
1ml of ethanol + 4ml of 30% NaOH
TEST
then add iodine solution drop by drop
till a yellow is produced then warm
gently with shake in WB for 10-15 min
(while heating the yellow color of the
solution will become faint so add iodine
again to restore the yellow color
The Result : formation of a pale yellow
precipitate

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 ETHANOL
State Liquid

Color Colorless

Odor Alcoholic Odor

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Dry Ignition - ve

• Dichromate test give green color

General tests
• Iodoform test give yellow Crystal

Special tests Estrification test give rotten apple odor

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COMPARISON BETWEEN METHANOL &
ETHANOL
Ethanol Methanol Item
√ √ Miscibility
√ √ Dichromate test
√ X Iodoform test
X √ Estrification
)wintergreen odor(
√ X Estrification
)rotten apple odor(
X X Borax test
√ √ Volatility

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COMPARISON BETWEEN METHANOL &
ETHANOL
Ethanol Methanol Item
√ √ Miscibility
√ √ Dichromate test
√ X Iodoform test
X √ Estrification
)wintergreen odor(
√ X Estrification
)rotten apple odor(
X X Borax test
√ √ Volatility

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 ALCOHOLS
(3. ISOPROPANOL)
Compound Class Structure formula

Isopropanol
Alcohol

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 ISOPROPANOL
State Liquid

Color Colorless

Odor Alcoholic odor

Dry Ignition -ve

Volatile
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 ISOPROPANOL

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Few sample with

a lot of liquid

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 Isopropanol

General tests • Dichromate test give green color

Special tests • Iodoform test give yellow Crystal

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 DICHROMATE TEST
Primary alcohols (RCH2OH) are oxidized to aldehydes and then to acids.
Secondary alcohols (R2CHOH) are oxidized to ketones. Tertiary alcohols
(R3COH) will not oxidize with potassium dichromate.

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 DICHROMATE TEST

1ml of alcohol + 1 ml of a solution of

potassium dichromate in sulphuric acid and
warm gently gives green color

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 IODOFORM TEST
Alcohols only containing the group give the iodoform reaction such as
ethanol and isopropanol.

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 IODOFORM
1ml of ethanol + 4ml of 30% NaOH
TEST
then add iodine solution drop by drop
till a yellow is produced then warm
gently with shake in WB for 10-15 min
(while heating the yellow color of the
solution will become faint so add iodine
again to restore the yellow color
The Result : formation of a pale yellow
precipitate

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 ISOPROPANOL
State Liquid

Color Colorless

Odor Alcoholic Odor

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Dry Ignition - ve

General tests • Dichromate test give green color

Special tests • Iodoform test give yellow Crystal

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 ALCOHOLS
(4. GLYCEROL)
Compound Class Structure formula

Glycerol Alcohol

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 GLYCEROL
State Liquid

Color Colorless / Viscous

Odor Odorless

Dry Ignition -ve

Viscous Not Volatile

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 GLYCEROL

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Few sample with

a lot of liquid

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 Glycerol

General tests Dichromate test give green color

Special tests Borax test disappear of pink color

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 DICHROMATE TEST
Primary alcohols (RCH2OH) are oxidized to aldehydes and then to acids.
Secondary alcohols (R2CHOH) are oxidized to ketones. Tertiary alcohols
(R3COH) will not oxidize with potassium dichromate.

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 DICHROMATE TEST

1ml of alcohol + 1 ml of a solution of

potassium dichromate in sulphuric acid and
warm gently gives green color

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BORAX TEST

Sol. In water
Pink
with ph.ph.

colorless

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 BORAX
Dissolve 0.5 g of borax in 5ml
TEST
water then add 2 drops of
phenolphthalein (ph.ph.) to obtain a
pink color
Take 1 ml of this solution and add
to it 1 ml of glycerol
disappear of pink color (not faint in
color)

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 GLYCEROL
State Liquid

Color Colorless / Viscous

Odor Odorless

Solubility H2O C. HCL 30% NaOH Na22CO33 sol.

in Miscible Miscible Miscible Miscible

Dry Ignition - ve

General tests Dichromate test give green color

Special tests Borax test disappear of pink color

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SUMMARY OF ALCOHOLS
Glycerol Isopropanol Ethanol Methanol
Liquid Liquid Liquid Liquid State
X √ √ √ Odor
X √ √ √ Volatility
√ X X X Viscosity
√ √ √ √ Miscibility
√ √ √ √ Dichromate test
X √ √ X Iodoform test
X X X √ Estrification
)wintergreen odor(
X X √ X Estrification
)rotten apple odor(
√ X X X Borax test

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