SUNWAY COLLEGE JOHOR BAHRU

AUSTRALIAN MATRICULATION PROGRAMME

CHEMISTRY UNIT 4 – ORGANIC CHEMISTRY AND CHEMICAL SYNTHESIS

ORGANIC REACTIONS

REACTIONS OF HYDROCARBONS

Addition Reaction of Alkene

1. Characteristics of addition reaction:

 occurs when two or more reactants combine to form a _________________.

 only occurs with _________________ compounds where the unsaturated bonds
are replaced by other atoms.
 2 new atoms are added ‘across the double bond’ and the double bond becomes a
single bond.
 occurs at a much faster rate than substitution reactions.
 general equation:

2. Alkenes or alkynes undergo addition reactions with substances like

_________________________________________________________________

3. Types of addition reactions:

Hydrogenation (H2(g))
Reagent Condition Example Product Observation

H2(g)

Halogenation (X2)
Reagent Condition Example Product Observation

Br2(aq) / no specific
bromine condition
water required

Unit 4 – Hydrocarbons 1
 Hydrohalogenation (HX)
Reagent Condition Example Product Observation

no specific
condition
HCl(g) required

Hydration (H2O(g))
Reagent Condition Example Product Observation

H2O(g)

4. Reaction with Br2 water is an identification test for alkene.

e.g. alkane can be distinguished from an alkene by adding an aqueous solution of

bromine, Br2(aq).

Observations with Alkene Observations with Alkane

the orange colour of the bromine water the orange colour of bromine water takes
disappeared rapidly / rapid a much longer time to disappear and uv-
decolourised, light is required / bromine water remained
orange.

Note:
For unsymmetrical alkene, the added H atom attaches to the C of the double bond already
having the most attached H atoms.
e.g. what is/are the products when but-1-ene reacts with HCl?

Unit 4 – Hydrocarbons 2
Substitution Reaction of Alkane
1. Alkanes and aromatic compounds are generally considered inert because of the strong
C–C and C–H bonds as well as being non-polar.

2. Common reactions of alkanes are: combustion and substitution.

3. Characteristics of substitution reaction:

 one atom is swapped with another atom.
 a H atom in alkanes or aromatic compounds is replaced by another atom
 need to occur at high T or in the presence of ____________________.
 slower than addition reactions.
 general equation:

4. For instance, in ultraviolet light, methane reacts with halogen molecules such as
chlorine and bromine.

Write equations for the reactions that occur.

Combustion of Hydrocarbon
1. Alkanes undergo combustion in air making them good fuels.

2. 2 types of combustion reactions:

Complete Combustion Incomplete Combustion

 produced CO2 and water vapour  produced CO, CO2, carbon and
water vapour

Unit 4 – Hydrocarbons 3
 OXIDATION OF ALCOHOLS

1. Two important oxidizing agents:

a) acidified potassium permanganate (MnO4–(aq)/H+ or acidified MnO4–(aq))
b) acidified potassium dichromate (Cr2O72–(aq)/H+ or acidified Cr2O72–(aq))

Which is a stronger oxidizing agent? _______________________

2. Oxidation of different types of alcohol:

 1o alcohols → ________________ → ___________________

 achieving partial oxidation is hard as there is strong tendency for the

aldehyde to oxidized to carboxylic acid once it is formed.
1o
 aldehyde can be produced by using an excess alcohol with the weaker
oxidizing agent. The mixture is also heated sufficiently to distill off the
aldehyde as soon as it forms.

 2o alcohols → __________________
2o
 ketones are resistant to further oxidation.

 no reaction as it is resistant to oxidation.

3o

Unit 4 – Hydrocarbons 4
3. You must be able to write equations and observations for these reactions.

Exam 2016 Section 2 Q27(iii) (2 marks)

Write observations for the changes occurring when the substances below are mixed. In your
answers include the appearance of the reactants and any product(s) that form.
(iii) acidified potassium permanganate solution and excess propan-2-ol

Exam 2016 Section 2 Q27(b) (3 marks)

Name the organic product and write the equation for the reaction when pentanal is added to
a solution containing acidified sodium dichromate.

REACTIONS OF CARBOXYLIC ACIDS

Acid-Base Reactions
1. Only the H atom of the –COOH
group that shows acidic
properties.

2. Has typical acid properties:

 turn blue litmus to red, taste sour
 produce H2(g) with reactive metals
 neutralized by a base
 produce CO2(g) with CO32– and HCO3–.

3. The reaction with NaHCO3 is used to distinguish carboxylic acid from other organic
compounds.

Adding NaHCO3 to a carboxylic acid gives effervescence / fizzing reaction, produces

colourless, odourless gas.

Unit 4 – Hydrocarbons 5
Esterification/Condensation and Hydrolysis Reactions
1. Esterification is a reversible equilibrium reaction between an alcohol and a carboxylic
acid to produce ________________________.

2. The reaction is catalysed by ______________________ and heated.

3. Write an equation to represent the reaction between methanoic acid and ethanol.

4. Esters can be converted back to the original carboxylic acid and alcohol when heated
with an acid or base. This reaction is hydrolysis. It is the reaction with water.

The products of hydrolysis depend on the conditions used.

acidic condition basic condition

Reagent used Products formed Reagent used Products formed
Heating with Heating with
H2SO4 or HCl strong alkali
(NaOH)

5. Equations for hydrolysis:

Acidic condition

Basic condition

Reaction with Ammonia

1. Carboxylic acid reacts with ammonia to produce _______________ and water.

Unit 4 – Hydrocarbons 6
 POLYMERISATION

Introduction
1. ________________are very large molecules made from the joining of many small
molecules known as _________________, in a process called polymerization.

2. Examples of polymers: nylon, DNA, protein, silk, wool, cellulose, polyester, oil, rubber,
Teflon etc.

3. A repeat unit is a part of a polymer whose repetition would produce the complete
polymer chain by linking the repeat units together successively along the chain.

4. Write ‘polymer’ and ‘monomer’ in the appropriate box for the following polymerization
process. Draw the structure of the repeating unit.

5. Two distinct processes are used for producing polymers:

(a) addition polymerization
(b) condensation polymerization

Addition Polymerisation
1. Alkenes can join together to form addition polymers.

2. Each monomer undergoes an addition reaction in which the double bond is broken
and new single C–C bonds form.

Unit 4 – Hydrocarbons 7
3. n – used to represent a large number of monomer units (monomer is repeated n times).

4. Name of the polymer includes prefix ‘poly’, followed by the name of the monomer, e.g.
polyethene.

5. Depending on the conditions, the addition polymer chain can form a:

(a) predominantly linear chain with little

branching – chains are closer and thus
dispersion forces are stronger, e.g. HDPE.

(b) chain with large amount of branching –

much weaker dispersion forces, e.g. LDPE.

6. Complete the following table (pg. 110 TB):

Polymer with at least 3 repeat

Name of Polymer Use and Property
units
polyethene / packaging, bottles, cling
polyethylene (PE) wrap, cable insulation

(soft, high strength, flexible,

heat resistance)

polyvinyl chloride pipes, water tanks, cable

(PVC) insulation, footwear, hose,
flooring, construction

(high strength, hard, stiff

and brittle)

polypropene / rope, carpet, plastic parts of

polypropylene (PP) cars, cup, bottle, luggage,
textiles, laboratory
containers

(tough, high strength,

flexible)

Unit 4 – Hydrocarbons 8
 Polymer with at least 3 repeat
Name of Polymer Use and Property
units
polytetrafluoroethene non-stick coatings for
/ Teflon (PTFE) cooking utensils, clothing,
cable insulation

(chemically very stable,

heat resistance, low friction)

polystyrene (PS) containers, disposable

cutlery and dinnerware,
packing material

(hard, brittle, flexible, heat

resistance).

Condensation Polymerisation
1. Condensation polymerisation:

(a) involves the joining of individual monomers by the loss of small molecules
(b) each monomer has two reactive functional groups
(c) produces a large molecule by eliminating a small molecule, like H2O.
(d) e.g. Kevlar, nylon, wool, silk, starch, cellulose.

2. Reactive functional groups involved are:

(a) di-carboxylic acid and di-alcohol – forming _________________

 joined by ___________________________.

Unit 4 – Hydrocarbons 9
  _______________________ present between the chains of linear polyesters,
such as poly(ethylene terephthalate), or PET and Terylene.

This strong force makes polyester extremely strong, durable and resistant to
most chemicals. They do not stretch, shrink and are resistant to wrinkles, mildew
and abrasion.

 The followings are the monomers for PET. Show the structure of PET formed.

(b) di-carboxylic acid and di-amine – forming __________________

 e.g. nylon, Kevlar, silk, wool and protein.

 joined by ____________________.

Unit 4 – Hydrocarbons 10
  able to form _________________ between the linear polymer chains. The
lone pair of electrons on the O atom from the carbonyl group (–C=O) of
one molecule able to form hydrogen bonds with a H atom from the N—H
group of another.

This ability greatly increases the tensile strength and stiffness of

polyamide.

 Draw the two monomers from which the following polymer is derived.

Types of Polymers

Thermoplastic
 soften without chemical change when
heated
 can be reformed and reshaped many
times (recycled)
 long chain linear with little cross linking
 prepared by addition polymerization
 polymer chains are held together by
weak dispersion forces.
 soft, weak and less brittle.
 e.g. PET, HDPE, PVC, nylon
Thermosetting
 formed by condensation
polymerization
 hard, strong and more brittle
 cannot be soften and reshaped again
and again
 if heated, the polymer just chars and
burns
 polymer chains are link by strong
covalent bonds
 e.g. bakelite, melamine resin, epoxy
resin, silicone, polyester

Unit 4 – Hydrocarbons 11
Exam 2016 Section 2 Q29 (9 marks)
Addition and condensation polymers are used in industry to produce a vast range of plastics.
Select one addition polymer you have studied and use it to complete parts (a) to (c).
(a) Draw and name the structure of the monomer used to produce this polymer. (2 marks)

(b) Draw and name the polymer, including at least three repeating units. (2 marks)

(c) State one use for this polymer, making reference to its relevant property/ies. (2 marks)

Kevlar is a condensation polymer utilised for its high strength. A section of the Kevlar
polymer is drawn below.

Unit 4 – Hydrocarbons 12
(d) Draw the two monomers from which Kevlar is derived. (2 marks)

Sample Exam 2016 Section 2 Q35 (9 marks)

Complete the table below, which relates to the properties and uses of plastics.
Select from the list below to complete the ‘Property’ column of the table. A property may only
be used once. State a different use for each polymer.

 hydrophobic
 high tensile strength
 biodegradable
 rigid
 chemically inert
 heat resistant

Unit 4 – Hydrocarbons 13