Chemistry Organic Chemistry

- Alkenes are used: In making polymers and alcohol.

―Alcohols‖
 Alcohol is a homologous series of hydrocarbon derivatives of general formula
(CnH2n+1OH).

 OH is the function group.

 Alkanol and the number in the name give the position of OH.
OH
CH3CH2CH2OH CH3CHCH3
[1-propanol] [2-propanol]

 Preparation of alcohols:
(1) Catalytic hydration of ethane (the chemical way):
OH
300°C / 60 atm
C═C + H ─ OH Phosphoric acid —C─C─
Ethene Ethanol

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The reaction is reversible and exothermic, high pressure and low temperature would
give the best yield. But in practice the reaction is carried out under optimum conditions
300°C, 60 atm and catalyst to give a decent rate.
(2) By fermentation of sugary solution (the biological way):
- Anaerobic fermentation by yeast fungus at 37°C and absence of O2.
- 37°C if higher temperature, the enzymes will be denatured.
- No oxygen to avoid oxidation of ethanol to ethanoic acid.
- The reaction stops after certain time because the % of ethanol reached the level that
killed the yeast or the mixture gets too warm.
Yeast fungus
C6H12O6(aq) Fermentation
2C2H5OH (aq) + 2CO2 (g) + energy

Ethanol by fermentation Ethanol by hydration

Advantages  Use of renewable resources  Fast reaction
 Waste plant material can be used  Run continually, just by removing
ethanol
 Produces pure ethanol. No need for
fractional distillation
Disadvantages  A lot of plant material used to  Made from non-renewable
make a liter of ethanol resources.
 Slow reaction.  Heat is needed which casts money.
 Yeast stops working after certain  The reaction is reversible. So the
time – even if glucose is left. Heat unreacted ethane and water must
of fraction distillation costs keep recycling.
money

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- Flammable, burns with clean blue flame

C2H5OH (l) + 3O2(g) 2CO2(g) + 3H2O(g)

- Less pollutant than petrol as no SO2.

 Ethanol is used:
- As fuel for cars (biofuel), as it is quite cheap, made from waste plant material
- Solvent in perfumes, glues (volatile) and food industry.
- Alcoholic drinks.
- Antiseptic.

― Organic Acids‖
 Organic or carboxylic acid is a homologous series of hydrocarbon derivatives of
general formula (CnH2n+1 COOH).

 Weak acid �partially ionized [pH ≈ 6]

 The function group is the carboxylic group (─ COOH)
 The name is alkanoic acid.

Ethanoic acid: CH3COOH

H O
H─C─ C─OH
H

 Ethanoic acid can be prepared by oxidizing ethanol.

[O]
C2H5OH CH3COOH

 The oxidation can be carried out in two ways.

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 Preparation of Ethanoic acid:

1) By fermentation- biological way:

Ethanol is left standing in air; bacteria bring about its oxidation to Vinegar or
Ethanoic acid (acid fermentation).

2) Using an oxidizing agent- Chemical way:

Ethanol is oxidized much faster by warming it with the powerful oxidizing agent
acidified potassium manganate (VII). The manganate (VII) ions Re reduced to Mn 2+
ions, with colour change. The acid provides the H+ ions for the reaction.
MnO4- + 8H+ + 5e- Mn2+ + 4H2O
Purple colourless
 Chemical properties:
1. Displacement reacts with metal forming salt and hydrogen
Mg(s) + 2CH3COOH (aq) (CH3COO)2Mg (aq) + H2(g)
Ethanoic acid Magnesium ethanoate

2. Esterification is a reaction between carboxylic acid and alcohol

Acid + Alcohol Ester + Water
HO H HO H
H-C-C-OH + HO-C-H H-C-C-O-C-H + H2O
H H H H
Ethanoic acid Methanol Methyl ethanoate Water
 Esterification is a condensation reaction
 The reaction is reversible; sulfuric acid acts as a catalyst.
 The alcohol part comes first in the name- but second in the formula (methyl
ethanoate / magnesium ethanoate).
 Many esters are having attractive smells and tastes. So they are added to
shampoos and soaps, and ice cream and foods as flavorings.

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Homologous Series:
 Is a family of similar compounds having:
1. Same functional group.
2. Similar chemical properties and reactions.
3. General formula.
4. Made by similar chemical reactions.
5. Their physical properties are predictable.
6. Each member differs by CH2 from the next one.

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Polymers
 Macromolecule: is a very large molecule made of repeating units.
 Polymer: is a very large molecule made of many monomer molecules.
 Monomer: is a small molecule that join together forming polymer.
 Addition polymerization: is the formation of polymer only by breaking double bond
of monomers. The monomers must have double bonds.
 Example:
Cl H Cl H
Δ / pressure
n C=C catalyst —C–C—
H H H H n
chloroethene poly chloroethene (PVC)
Plastic
The chains are not all the same length. This is why we cannot write exact formula for
PVC or any polymer.

 Plastic:
- Most plastics are made from chemicals in the naphtha fraction of petroleum
- Can be molded into shapes without breaking.
 (PVC): Used in hoses, water pipes & electric insulators.
 Polyethene: Can be used in making bowls, plastic bottles and plastic bags.

 Condensation polymerization: a reaction in which there are two products, the

polymer and a smaller one.
- Does not depend on C=C bonds
- Two types of monomer join. Each has two function groups.
- They join at their function groups by eliminating a small molecule.
 Example: in making synthetic fibers  (Teryelne & Nylon).

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Synthetic Polymers
Synthetic polymers : are polymers are made in factories. Ex. Terylene, lycra,
chewing gum, and plastics as polystyrene and Perspex.

 Nylon: [polyamide]
O O H H O O H H
HO – C – – C – OH + H – N – –N–H –C– –C–N– –N
n
+ n H2O
di carboxylic acid + diamine polyamide + water

O H
—C—N— (is amide linkage)
- Nylon is used in making tough, strong fibers which is used in threads, ropes, flying
kits, fishing nets. Parasails and parachutes.
 Terylene: [polyester]
O O O O
HO – C – –C–OH + HO – – OH – C– –C–O– –O–
n

+ n H2O
Dicarboxylic acid + diol polyester + water

O
—C—O— (is ester linkage)
- Polyester is used in making shirts, threads, and polyester-cotton blended fabrics
(more hard wearing than cotton and does not crease so easily).

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 Advantages of synthetic fibers:

1. Light and do not conduct heat or electricity(insulators)
2. Can be coloured.
3. Do not corrode, and durable (not affected by air water and chemicals) water proof.
4. Strong because their molecules are attracted to each other.
5. Their properties can be changed by changing the monomers and the reaction
conditions.

 Disadvantages of synthetic fibers:

Polyethene is the biggest problem. It is the most used plastic in the world as 5 trillion
plastic bags are made every year. So they cause many problems:
1. Fish, birds, and other animals eat them and starve to death.
2. They clog up drains and sewers, and cause flooding.
3. Some river beds now contain a thick layer of plastic getting in the way of fish.
4. Non-biodegradable: not broken-down in the environment by microorganisms.
5. Rubbish is collected and brought to landfill sights causing sight pollution.
6. Plastic is flammable, when burns releases toxic gases.
N.B. Polymer wastes can be recycled.
 Some are melted down and made into new products.
 Some are melted and cracked to make small molecules that are polymerized into new
plastic.
 Some are burnet, and heat is used to produce electricity.
What are the advantages and disadvantages of recycling polymers?
 The best long-term solution to disposal would be to work on degradable plastics
 Biodegradable plastics contain some additives as starch that bacteria can feed on.
 Photodegradable plastics contain additives that breakdown in sunlight.
 Biopolymers grow in plants, or made in tanks by bacteria.

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Natural Polymers
 Photosynthesis: is a photochemical reaction by which chlorophyll acts as a catalyst
that traps sunlight in presence of H2O and CO2 to produce glucose sugar.
 Plants use glucose as monomers to make starch and cellulose i.e. Carbohydrates.
 Plants use glucose, plus nitrates from the soil to make amino acids.
 Plants use amino acid molecules as monomers to make proteins.

Glucose sugar Polymerization Starch & Cellulose

enzymes
Energy store builds stem

and cell wall

Glucose sugar Enzymes Proteins & Fats

 The wood in trees is 50% cellulose

 The polymer in your hair and nails. And in wool and silk and animal horns and
claws, is called keratin.
 The polymer in your skin and bones is called collagen.

 Starch [polysaccharides]

HO – – OH + HO – – OH –– – O ––
n
Glucose
C6H12O6 C6H10O5
1:2:1 carbohydrates
+ nH2O

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 Protein:[polyamide / peptide]

O H O H O H O H
HO– C – – N –H +HO – C – –N–H –C– –N – C – –N–
n
+ n H2O
22 different amino acid are used in building proteins.
 N.B. Protein & Nylon have same amide linkage but different in their monomer.
O O O
HO – C – – NH2 HO – C – – C – OH + H – N – –N–H
amino acid dicarboxylic diamine

Fats / Oil: [polyester linkage]

H O H O
H – C – OH HO – C – H–C–O–C–
O O
H – C – OH HO – C – H–C–O–C–
O O
H – C – OH HO – C – H–C–O–C–
H H
Glycerol Fatty Acid Long-chain hydrocarbon

H2 / Δ
Saturated Ni Unsaturated
(Fats) (Oil)
[Harmful] [Useful]

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 Uses of fats:
1. Energy store.
2. Stored in cells to keep the body warm.
3. Cell membrane.

Hydrolysis of Polymer
- Is breaking down of long chain molecule by reaction with water.

Hydrolysis
Polymer Monomers
 Reagents for hydrolysis:
 Acidic: HCl(aq) / Δ + H2O [HCl is a catalyst]
 Alkaline: NaOH(aq) / Δ + H2O

 Acidic hydrolysis:
Terylene Diol + Dicarboxylic acid
Nylon Diamine + Dicarboxylic acid
Starch n Glucose
(Can be identified by chromatography using locating agent)
Protein Amino acid
Fat / Oil Glycerol + 3 Fatty acid

 N.B. Digestion is an acidic hydrolysis.

 Alkaline hydrolysis:
Δ
Fat / Oil + NaOH(aq) Glycerol + Sodium salt of fatty acid
(soap)
i.e. Saponification reaction

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