ALCOHOL

The Alcohol Family

1. One of member of homologous series which contain carbon,
hydrogen and oxygen.

2. General formula for alcohol is CnH2n+1OH. [n=1,2,3..]

3. Alcohol contains the hydroxyl group, -OH as their functional

group. [notes: not hydroxide ion, OH- , alcohol not is alkaly ]

4. Alcohol is neutral compound.

5. Alcohol are named by replacing -e for alkane with –ol.

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6. Structural formula and molecule for few alcohol.

Molekul
n Name Mr Structural formula
Formula
H
|
12+3+ CH3OH
H— C — OH
1 Methanol 16+1 @
|
= 32 CH4O
H

H H
12x2 + | |
Ethanol C2H5OH
5 +16 H— C — C — OH
2 very @
+1= | |
important C2H6O
46 H H

H H H
| | |
Propan-1- H — C— C — C — OH
3 60 C3H7OH
ol | | |
H H H

Butan-1-
4 74 C4H9OH
ol

Pentan-1-
5 88 C5H11OH
ol

Hexan-1-
6 102 C6H13OH
ol
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Q: Give names for this alcohol.

OH

CH3  CH2  CH  CH2  CH2  CH3

Formula: C6H13OH

Name : HEXAN-3-OL

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Naming Alcohol
1. Find the longest continous carbon chain containing –OH.
2. Number the carbon beginning at the end nearer to the – OH,
write the number in front of the ending –ol.
3. Locate the alkyl group (branch chain), give number to the
carbon and named the alkyl group. Put the number in front of
the group.
 CH3 : methyl
 C2H5 atau CH2CH3 : ethyl
 C3H7 atau CH2CH2CH3 : propyl

4. Complete the name for the alcohol

(ii)

OH

CH3  CH2  C  CH2  CH2  CH3
|
CH3

Formula: C7H15OH
Name : 3-methyl hexan-3-ol

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(iii)

OH

CH3  CH2  CH  CH  CH2  CH3
|
CH3

Formula : C7H15OH
Name : 4-methyl hexan-3-ol

(iii)

OH

CH3  CH  CH  CH  CH2  CH2
| |‌‌ |
CH3 CH3 CH3

Formula : C9H19OH
Name : 2, 4 – dimethyl heptan-3-ol

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 (iv)

C 2H 5 OH
 
CH3  CH2  CH  CH2  CH  CH2 ─ CH3

Formula : C9H19OH
Name : 5-ethyl heptan-3-ol

Physical Properties
1. Liquid at room temperature. (pg. 62) [ no gas]
2. Simple alcohol are very soluble in water, infinite solubility.
Methanol, ethanol dan propan-1-ol is miscible in all proportions
(terlarut campur dengan air dalam semua kadaran).
The rest of the alcohol less soluble or insoluble.

Isomerism
Similar to alkenes, isomerism in alcohol results from the
branching of the carbon chain and the different location of the
hydroxyl group.

You only have to know the isomerism in propanol dan butanol.

Q : Draw 2 isomers for propanol and 4 isomers for butanol,

and dan named the isomers.

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Propanol

Butanol

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Propanol

H H H
│ │ │
H ─ C ─ C ─ C ─ OH
│ │ │
Molecular formula: C3H7OH
H H H
Name: Propan-1-ol

H H H
│ │ │ Molecular formula: C3H7OH
H─C─C─C─H
│ │ │ Name: Propan-2-ol
H OH H

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Butanol

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 H H H H
│ │ │ │ Molecular formula: C4H9OH
H ─ C ─ C ─ C ─ C ─ OH
│ │ │ │ Name: Butan-1-ol
H H H H

H H H H Molecular formula: C4H9OH

│ │ │ │
H─C─C─C─C─H
│ │ │ │ Name: Butan-2-ol
H H OH H

H H H
│ │ │ Molecular formula: C4H9OH
H ─ C ─── C ─── C ─ OH
│ │ │ Name: 2-methylpropan-1-ol
H H─C─H H
│
H

H OH H
│ │ │ Molecular formula: C4H9OH
H ─ C ─── C ─── C ─ H
│ │ │ Name: 2-methylpropan-2-ol
H H─C─H H
│
H

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ETHANOL
1. Preparation of ethanol.
i. Laboratory preparation (fermentation)
ii. Industrial production (hydration process)

Making Ethanol Fermentation

1. Two stages;
i. Fermentation
ii. Purification
- through fractional distillation at 78 oC
( boiling point of ETHANOL)

Fermentation of Glucose
1. Yeast is added to sugar or starch.

2. Anaerobic process ( takes place in the absence of oxygen).

3. Yeast releases enzymes. These enzymes break down the

sugars/starch into glucose, C6H12O6.

4. Zymase slowly decomposes the glucose to form ethanol and

carbon dioxide.

Zymase @ C2H5OH @ C2H6O

C6H12O6 (aq)  2CH3CH2OH (l) + 2CO2 (g)
o
30 C

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 Delivery tube

Conical flask
Beaker
Glucose + yeast Lime water

When the concentration of ethanol reach 15%, the yeast dies.

Q: How to produce pure alcohol?

A: Purified the ethanol through fractional distillation.

Purification of Ethanol
1. Ethanol produced from the fermentation process is impure,
because its mix with the glucose solution.

Q : Draw labeled diagram to carry out the purification of ethanol

through fractional distillation process.

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 ○
Thermometer

Water out
Fractioning
collum ●

Liebig
condenser

Retort stand
with clamp

Rounded
Water Water in
conical
Product from
fermentation Porcelain Distillate
Wire XXXXXXXXXXXXXXX chips (Ethanol)
gauge
Bunsen
burner

Q: Why the solution/filtrate in rounded conical must heated at

78oC.

A: The boiling point of ethanol is 78 oC.

Q: Ethanol produced may still contains of some water.

What should be done to be sure that ethanol is 100% pure?

A: Anhydrous calcium oxide or anhydrous calcium chloride is

add/put into the ethanol.

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Q: What is the function of;
- thermometer
- porcelain chips
- Liebig condenser

A: thermometer is used to ensure that temperature is always

at 78 oC.

B: Porcelain chips is used to avoid the solution jumped/

effervesence (breaking bubbles)

C: To cooled the ethanol vapour to become liquid.

Q: Named the process in Liebig condenser.

A: Condensation

Q: What is the properties of ethanol

A: Properties;
- colourless
- volatile
- good organic solvent
- miscible with water
- highly flammable
- antiseptic
- chemically reactive

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Q: What is the uses of ethanol

A: Uses;
- As a solvent in perfumes/cosmetics
- As a thinner in varnish, ink
- As a cleaner for compact disc.
- As a fuel for transport
- As a raw material for the manufacture of vinegar,
- As a raw material to make industrial product such as
antiseptic and cough syrup.

Industrial production of ethanol

Ethene is mix with steam is passed through concentrated

phosphoric acid (catalyst) at 300 oC (temperature) and 60
atmosphere (pressure).

H3PO4
@ C2H4 concentrsted C2H5OH
CH2 = CH2 + H2O —————→ CH3CH2OH
300 o C, 60 atm
[we already studied this prosess ok in alkene chemical properties]

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Chemical Properties

1. Combustion

i. Alcohol are very flammable sustances.

ii. Ethanol burns with non-smoky and blue flame and releases
lot of heat. Suitable for use as fuel, described as clean fuel.

C2H5OH + 3O2  2CO2 + 3H2O

Ethanol Oxygen Carbon Water
dioxide

Q: Write combustion equation for hexanol

C6H13OH + 9O2  6CO2 + 7H2O

hexanol Oxygen Carbon Water
dioxide

2. Oxidation
i. Ethanol can be oxidised into ethanoic acid by an oxidising agent.

[Ethanoic acid is a family of carboxylic acids]

CH3CH2OH + 2[O]  CH3COOH + H2O

Ethanol Ethanoic acid

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Q: Show the structural formula for the equation above.

H H H O
| | | ║
H — C — C — OH + 2[O] → H — C — C — OH + H2O
| | |
H H H

Q: Named 2 solutions are commonly used as oxidising agent.

(i) Acidified potassium manganate(VII), KMnO4

(purple to colourless / decolourised)

(ii) Acidified potassium dichromate(VI), K2Cr2O7

(orange to green)

Q: Draw a labeled diagram for the process.

Ethanol +
potassium dikromat(VI) +
concentrated sulfuric acid

Heat

Distillate Cold
(ethanoic acid) water

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Prosedure:
1. 10 cm3 of acidified potassium dichromate(VI), K2Cr2O7 /
acidified potassium manganate(VII), KMnO4 is poured into a
boiling tube.
2. 3-4 drops of alcohol is added
3. The mixture is heated gently until the mixture boils.

[practical book pg 42]

Distillate (ethanoic acid)

- Colourless
- Vinegar smell
- Blue litmus paper turns red (acidic properties)

3. Dehydration

- H2O
ALCOHOL → ALKENE

1. Converted ethanol into ethene and a molecule of water.

2. The elimination of water results the formation of a carbon-carbon

double bond.

3. Dehydration occur when

a. ethanol vapours is passed over a heated catalyst such as.
i- Porous pot / porcelain chips
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 ii- Purnice stone / aluminium oxide, Al2O3 /alumina

b. Ethanol is heated under reflux at 170 oC with excess

concentrated sulphuric acid.

CH3CH2OH  CH2 = CH2 + H2O

Ethanol Ethene

Q : Draw the structural molecule for the process

H H H H
| | | |
H—C—C—H → H — C ═ C — H + H 2O
| |
H OH

Q : Draw labeled diagram.

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 Glass wool
soaked with Porcelain
ethanol chips

Ethene
gas

Delivery Retort
Heat Heat Test stand
tube tube with
clamp

Water

Procedure at pg. 43-44 prac book must see

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com

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