Module 7 KISS Notes (HSC Chemistry)

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KISS Resources for NSW Syllabuses & Australian Curriculum
® KEEP IT SIMPLE SCIENCE

keep it simple science Chemistry Module 7
Organic Chemistry
WORKSHEETS
Worksheet 1 Names of Organic Chemicals
Answer in the spaces provided Student Name..........................................
1. 5.
The various homologous series have different Sketch the structural formula for:
name endings, but the prefixes follow the same
rules. How many carbon atoms in: a) 2-chloropropanal
a) pentanone? b) butanal?
c) propanamine? d) octyne?
b) 2-methylbutanoic acid
e) methanoic acid? f) hexanol?
2.
Name each compound from its formula. c) 1,1,3,3-tetrafluoropentane
a) C5H12 ...............................................
b) C3H7COOH ....................................................
d) 4-methyl-2-pentyne
c) C6H13OH .....................................................
d) C4H6 ..................................................
e) C2H5Br ....................................................... e) 3-ethyl-2-hexanone
3.
A student describes a branched-chain alkane as
“2-ethylbutane”.
6.
a) Sketch the structure suggested by this name. Name each of the following:
H Cl
O-H
a)
H C C C
H Cl O
b) Explain why this name is incorrect and give the b) CH3 CH CH CH CH3
correct name.
CH3 CH3 CH3
Br
c)
Br C C C CH3
4.
Sketch the structure and give the name for the Br
simplest tertiary alcohol.
H
d) CH3 CH CH C
CH3 Cl O
CH3
e)
CH2 C CH2
F OH F
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Worksheet 2 Reactions of Hydrocarbons
keep it simple science Answer in the spaces provided. Student Name......................................
(on reverse, if insufficient room)
Write a balanced equation (states not required) for: 4. the addition reaction between Br2 and
a) 1-pentene. Name the product(s).
1. the complete combustion of:
a) butane.
b) 2-pentene. Name the product(s).
b) propyne
5. the addition reaction between H2O and 1-butene.
2. a single substitution reaction between F2 and:

a) ethane.
6. propene reacting with HF.
b) hexane.
3. the addition reaction between H2 and butene.

Tutorial Note: You should see in Q5 & Q6 that two
isomers are possible products of each reaction. Both
isomers will form, but one will predominate according
to “Markovnikov’s Law”. Research this, and name
ONLY the predominate isomer in your answers above.
Worksheet 3 About the Hydrocarbons

Fill in the blanks Student Name......................................
The huge variety of carbon compounds is due to Melting and boiling points show a very regular
the ability of carbon atoms to each form pattern of rising steadily as molecular size
a)................. (number) b)................................ bonds. p).....................................
Carbon atoms readily bond with each other
forming c).........................., rings or networks. The alkenes have very q)................................
They can form single, d)............................ or properties to the alkanes. Alkenes contain one
............................ bonds. r).......................................... bond, and have general
formula s)....................................
The simplest carbon compounds, containing only
carbon and hydrogen, are collectively called the The alkynes have a t).......................... bond and
e)............................................., of which there are 3 general formula u)......................................
f)................................... series. These are the
g).........................., ............................ and ...................
Another property of hydrocarbons is that they are
Hydrocarbons are named by using a prefix for the highly volatile. This means that they tend to
number of h)........................................, and adding v)............................. readily. This has important safety
an ending to identify which precise type it is. consequences for these highly inflammable,
w)...................-energy compounds.
The alkanes have names ending in “i).....................”.
They all contain j).......................... C-C bonds and Crude petroleum is a complex x)............................. of
have a general formula k)............................... many compounds. At a refinery, it is separated into
Alkanes are l)................................ in water and have useful “y)..................................” by the process of
relatively m).................... melting and boiling points. z)............................ ....................................... The crude
Their properties relate to their molecules being mixture is vaporised and as the vapours rise and the
non-n)...................... The only inter-molecular forces temperature aa).............................., each fraction
are the very weak o)............................................ ab)................................... at a different level in the
forces. tower and is collected separately.

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® Worksheet 4 Practice Questions

Multiple Choice Questions 7.
a) Plot the following data on the grid provided.
1. The compound with molecula formula C15H32 is
likely to: The boiling points (oC) for some alkenes:
A. be a member of the alkene homologous ethene -104
series. propene -48
B. contain a triple carbon-carbon bond. hexene 64
C. have a name ending in “-ANE”. heptene 94
D. have polar molecules.
100
2. The molecular
Boiling Point (oC)

model shown is
A. pentene
B. butene
0
C. propane
D. butane
3. Which of the following is NOT a property of the
-100
alkanes?
A. soluble in water 1 2 3 4 5 6 7 8
B. relatively low melting & boiling points
No. of Carbon Atoms
C. non-conductors of electricity
D. hydrophobic b) Use the graph to estimate b.p.’s for butene and
pentene.
4. In petroleum refining, fractional distillation separates
the mixture according to differences in:
A. melting point
B. density c) Account for the generally low mp & bp of the
C. solubility hydrocarbons.
D. boiling point
5. The reaction between 2-hexene and Br2 would

produce:
A. 2,3-dibromohexene. 8.
B. 2-bromohexane + HBr. Write a balanced chemical equation (no states) for:
C. 2,3-dibromohexane.
D. a variety of isomers of bromohexane. a) the complete combustion of hexane.
Longer Response Questions

6.
a) Explain, with the help of simple equations or b) the addition reaction between water & propene.
diagrams, how the substitution reaction between an
alkane (say methane) and a halogen (say Cl2)
proceeds when exposed to UV light.
9.
Give an outline of:
a) the difference between saturated & unsaturated
hydrocarbons, with examples.
b) differences in the geometry of hydrogen atoms

attached to carbon atoms with single, double and
b) Explain, with a simple example, how this reaction triple C-C bonds.
may result in a mixture of multiple products.

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® Worksheet 5 The Alcohols

keep it simple science Fill in the blanks Student Name......................................
The alkanols are an a)...................................... series
Fermentation can produce a mixture containing a
of carbon compounds with general formula
maximum ab)...............% ethanol. This can be
b)................................... They are also as the
purified by ac).............................. to obtain about
“c).............................” Each alkanol has an
ad)............% purity. Industrial scale fermentation
d)............. group attached to a carbon atom. This
(apart from beer & wine production) uses materials
group contains a e).................... covalent bond
from the ae)........................................ industry, and
which creates an electric f)............................... on the
then fractional af).............................. to obtain near-
molecule. This causes quite strong g)........................
pure ethanol for making ag)............................... (food
bonds between the molecules, which result in the
use) or for solvent and cleaning purposes.
following properties:
When alkanols burn, the products of complete
• m.p.’s & b.p.’s are h)................................ than the
combustion are ah)............................................. and
corresponding alkanes.
..................................
• alkanols are generally i)............................. in water.
• they are excellent j)..................................., because
The “Molar Heat of Combustion” is defined as
they can dissolve both k).............................. and
ai).......................................................................... with
................................. (opposites) solutes.
all reactant & products in their
• they are inflammable, and can be used as
aj)...................................
l)......................, although their m).........................
...................... is lower than the alkanes.
Although the reaction is always ak)..............-thermic
and should have a al)............................. value for ∆H,
Ethene can be converted to ethanol by an
the value is stated as a am)....................................
n).......................... reaction, adding o).....................
quantity because of the definition.
across the double bond. Dilute
p)................................ acts as a catalyst for this
Generally, the values for ∆Hc for the alkanols
reaction. The reverse reaction, converting
an)................................ with increasing molecular
q)............................ to ................................ is also
size, but are much lower than the values for an
possible if r)........................ H2SO4 is the catalyst.
ao)...............................
This reaction could be considered as a
“condensation”, but is usually referred to as
The advantages of using ethanol as a fuel are
“s)......................................”
• it is a ap).......................................... resource
• the aq).................................... is known & proven
Biologically, ethanol can be made from
• it is “ar)...................................-friendly”
t)....................... by the process of u)............................
• it can be mixed with petrol to about as)...........%
The catalysts are the v)............................. in living
without any modifications to existing car engines.
w)..................... cells.
The requirements for the reaction are:
Disadvantages include:
• a suitable source of x)........................ from fruits or
• to totally replace petrol, vast areas of land would
grains.
have to be at)...............................................
• live y)............................
• large amounts of energy are needed for the
• temperature maintained around z).........oC
au)....................................... process, and we cannot
• aa)................................. conditions (no oxygen).
yet do this in a renewable and eco-friendly way.
• vehicle av).............................. would have to be
totally re-designed and replaced to run on pure
ethanol.

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® Worksheet 6 Alcohols Again

keep it simple science Guided Notes & Questions Student Name................................
(Make your own summary)
1. 4.
Account for the fact that the alcohols have much Give the structural formula and name for the
higher mp’s & bp’s than the corresponding alkanes. product of the reaction of concentrated HCl with:
a) 1-butanol
b) 2-butanol
2.
Outline the conditions required for fermentation and 5. Outline the “alcohol dehydration” reaction,
summarise the overall reaction with an equation. including reactants, products and catalyst involved.
6.
Summarise the differences between the oxidation
3. (with potassium dichromate) of primary, secondary
In an experiment butanol was burned under a “tin- & tertiary alcohols.
can calorimeter” containing 50g of water, initially at
18oC. After burning 0.60g of butanol, the water
temperature rose to 47oC.
a) Write a balanced equation for this combustion.
b) Calculate the “heat of combustion” from this

data, per gram AND per mol.
7.
a) Ethanol, as a fuel to replace petrol, is described
as being “renewable”. Explain why.
c) The listed value of ∆Hc = 2676 kJmol-1.

Comment on the accuracy of this experiment and b) Ethanol is also claimed to be “carbon-neutral”.
analyse possible reasons for errors. What does this mean?
c) Is it actually “carbon-neutral” with current

technology? Explain.
d) Suggest ways to improve the reliability of the

experiment.
d) What is the major problem with the idea of totally
replacing petrol with ethanol fuel?

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® Worksheet 7 Esters
The alkanols, also called a)..................................., all Esters are made using the technique of
contain the functional group b).................. and have p).................................... The reaction flask is open to
the general formula c).................................... The -OH the atmosphere to avoid any dangerous build-up of
group contains a chemical bond which is q)................................... Volatile chemicals vapourise,
d)..............................., and allows e)............................. but are r)..................................... by the
bonding between molecules. This is why the s)................................................ and drip back into
alkanols have m.p’s & b.p’s much higher than the the flask. t).................................... is used as a
corresponding f)......................................... catalyst and also improves the yield by shifting the
u)............................., because it absorbs water.
The alkanoic acids contain the functional group
g)...................... This group contains 2 polar bonds, Esters occur widely in nature, being responsible for
so 2 h)............................... bonds can form between many of the v)......................... and
molecules. This is why i).............................................. .................................. of foods, especially
................................... than the alkanols. w).......................... Long-chain esters of glycerol are
the x)............................ and ............................
Esters are formed by the reaction of j)........................
with ........................................... The other product is Artificially manufactured esters are used as
k)................................. Esters are named by the y)........................ .................................. in processed
l)........................... first (with its ending changed to foods, as z).......................... in industry and as
m)..........), followed by the n)...................................... ingredients in many products such as
name (with its ending changed to o)..........................) aa)............................. and .........................
Worksheet 8 More Esters

Practice Exercises Student Name......................................
1. Names of Esters c) i)
Name the ester formed from: ii)
a) ethanol & propanoic acid iii)
d) i)
b) propanol & ethanoic acid ii)
iii)
c) pentanol & methanoic acid e) i)

ii)
iii)
d) methanol and pentanoic acid
f) i)
ii)
e) hexanoic acid and butanol iii)
3. Names from Structures

f) ethanoic acid and octanol For each of the following esters:
i) give the name of the ester
2. Condensed Structural Formulas ii) name the alkanol and acid use to make it
For each of the compounds above, give the
condensed structural formula for the a) HCOO(CH2)3CH3
i) alkanol
ii) alkanoic acid
and iii) ester b) CH3CH2COO(CH2)3CH3
The first has been done for you as an example.

Answer c) CH3(CH2)3COO(CH2)4CH3
a) i) ethanol = CH3CH2OH
ii) propanoic acid = CH3CH2COOH
iii) ester = CH3CH2COOCH2CH3 d) C4H9COOCH3
Note: although the alkanol comes first in naming, it may
be more convenient to place the acid remnant first in the
e) C5H11COOC7H15
structural formula. This system is used here.

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® Worksheet 9 Fats, Oils, Soap, Detergents

keep it simple science Student Name................................
Guided Notes & Questions
Answer in the spaces provided. 3.
(on reverse, if insufficient room) a) What is an “emulsion”?
1.
a) Describe the chemical structure of a “fatty acid”.
b) Explain how emulsification results in cleaning

things.
b) Draw the structural formula for “glycerol”.
c) Explain, with the aid of simple diagrams, how

soap acts as an emulsifier.
c) Use a labelled, schematic diagram to explain the
structure of a triglyceride. Explain why it is an ester.
4.
2.
Compare a soap molecule with a typical detergent
a) Name the process by which soap is made, and
molecule to outline
write a word equation for the process.
a) any basic similarity in structure and properties.
b) performance as emulsifiers in “hard water”.

b) Give an outline of a simple procedure by which
soap can be made in the laboratory.
Worksheet 10 Organic Acids & Bases

Answer in the spaces provided. Student Name......................................
3.
1. a) Complete this general equation to show how an
a) Complete this general equation to show how a amine acts as a Bronsted-Lowry (B-L) base in water
carboxylic acid acts as a Bronsted-Lowry (B-L) acid solution.
in water solution.
R-NH2 + H2O
R-COOH + H2O
b) Identify the B-L acid and B-L base in the reaction

b) Identify the B-L acid and B-L base in the reaction above AND the conjugate partner of each.
above AND the conjugate partner of each.
4. Name and give formula for the conjugate acid of:
2. Name and give formula for the conjugate base of:
a) butylamine.
a) butanoic acid.
b) methanoic acid. b) dimethylamine.
c) octanoic acid. c) octylamine.

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® Worksheet 11 Reaction Pathways

2.
A pure organic compound is liquid at room Write the balanced equation for a possible reaction
temperature. It has an empirical formula C3H8O and of sample P with conc. HCl.
a molecular mass about 60.
Name the organic product of this reaction.
It was divided into 4 identical samples labelled
P,Q,R & S. Each of these was subjected to a
different chemical treatments as follows:
1. Sample P
was treated with concentrated HCl.
A new organic compound was formed, plus water. 3.
a) During the reaction of Q-2 & R, what is the
2. Samples Q and R significance of the “noticeable odour”?
Q was treated with acidified dichromate ions with
strong heating and reflux. A new organic compound
formed.
b) What therefore, is the identity of the product
This product was labelled “Q-2”. which was labelled Q-2?
Q-2 was separated & purified, then reacted with
sample R under reflux in the presence of
concentrated sulfuric acid. c) Look back to Q1.
If there was a possibility of isomers, what does the
At the end of the reaction, a noticeable odour identity of Q-2 tell you? Explain.
resembling pineapple was present.
3. Sample S
was treated with concentrated H2SO4. The sample
was dehydrated, forming a gaseous product.
d) Write a word equation for the reaction between
The gas was collected, then some brown Br2(aq) was Q-2 and sample R.
introduced into the flask. The bromine immediately
discoloured and a colourless liquid began to
condense in the flask. e) i) In the earlier reaction with sample Q, what was
the purpose of the acidified dichromate reagent?
Now Come the Questions...
1.
Using the clues in the first paragraph, identify the
starting compound. Explain your reasoning. ii) What was a probable intermediate product in the
conversion
If more than one isomer is possible, identify them Q intermediate product Q-2
specifically and show structural formulas.
4.
Using structural formulas, describe the reactions
which occurred to sample S.
All organic compounds should be named.

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® Worksheet 12 Polymers
When petroleum is refined the main products are The plastic is ac).......................... and more
for use as a).............................., but there are also ad).......................... so it is used for
other chemicals extracted for use in manufacturing. ae)........................................................
These chemicals are collectively called
“b)...................................................” and the most Polystyrene is made from the monomer
important is c)...................................... af).......................... for which the correct systematic
name is ag)........................... .................................. The
The reason for ethene’s great usefulness is the “side group” on this molecule is the ring-shaped
d)................. carbon-carbon bond. This bond is ah)............................ group. This increases the
highly e)..................... and readily “splits open” molecular mass so that the ai).............................
allowing other atoms/groups to join onto the forces hold the polymer molecules even more
molecule. This is called an f)............................... strongly so the plastic is aj).......................................
reaction. and ..............................
In the laboratory, compounds containing a double Polymers can also form by a ak)..............................
bond can be identified using a solution of reaction. This occurs when 2 monomer molecules
g).......................... If this is added to an alkene, the join together by elimination of a al).............
g).......................... will be h)............................ ..................................... Examples of condensation
because of an addition reaction. With an alkane, the polymers are nylon and am).....................................
colour may change and shift from one solvent to All biological polymers, such as an)............................
the other, but will not be h)....................................... and ...................................... are condensation
polymers.
The yield of ethene from petroleum is greatly
increased by the process of “i)..................................” One important biological polymer is
in which long-chain alkanes are broken into smaller ao)................................. which is a polymer of
fragments by either j)............................... or ap)................................. and is found in large
........................................ This increases the yield of amounts in all plants, where it forms the cell
valuable fuel fractions such as k)................................ aq)...................... which strengthens and protects all
and increases the yield of ethene which is extracted plant tissues. We already use cellulose for fabrics
from the l).......................... fraction. such as ar)............................ and .................................
and process it to make as)............................... When
The major use of ethene is the manufacture of the petroleum supplies run out, cellulose has great
m)...................................... Thousands of ethene potential to supply our needs.
monomers join together by n)...............................
reactions to form o)................................................ If Its monomer at).......................... can easily be turned
the reaction is carried out at high p).......................... into the alcohol au)............................. which can be
and ............................. with an “initiator” chemical, used as a fuel, or chemically converted to
the result is q)...................-density polyethylene. The av)................................... to feed the plastics
long chain molecules have many r).......................... industry. Unfortunately, we have not yet developed
........................ and cannot pack close together, so a simple, efficient and economical way to convert
the plastic is soft and s).................................., ideal cellulose to aw)............................. to begin the
for soft plastic bags and t).............................. film. process.
If the reaction is carried out at lower pressure and Research is also progressing in the use of
temperature with a u)......................................, the engineered “biopolymers” such as ax)..................
polymer molecules lack branches and can (abbreviation). This polymer has properties similar
v)........................... ................................... to form to some petrochemical plastics, but is made
w)......................-density polyethene, used (for naturally by microbes such as the bacterium
example) in x)........................... .................................. ay)................. ............................. (scientific name).
The Monsanto company has used az).........................
Other important polymers include P.V.C. which ........................... techniques to transfer the genes for
stands for y).............................................................. PHB into ba).......................... plants. After normal
The monomer is commonly called z)...................... growth and harvesting, PHB can be extracted from
................., but its correct chemical name is the “waste” leaves and stems of the crop.
aa)...................................................
Although this is very promising, it is unlikely to be
The added chlorine atom makes the molecular used on a large scale while cheaper petrochemicals
mass much higher, so that the ab)............................... are still available.
forces between molecules are stronger.

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® Worksheet 13 Practice Test-Style Questions

keep it simple science Student Name......................................
Multiple Choice 8.
1. If propene (C3H6) underwent an addition reaction Explain, using chemical equation(s) when needed,
with water, the correct structural formula for the why liquid hexene will de-colourise a bromine
product would be solution, but liquid hexane will not.
A. H H H B. H OH H
H C C C H H C C C H
H H H H H H
9.
C. H H O-H D. H H O-H The main industrial source of ethene is “cat-
cracking” of certain molecules in petroleum.
H C C C H H C C C H a) Outline the general process of “cat-cracking”,
H H H H O-H including the meaning of the term.
2. Alkenes can be identified by their reaction with

bromine water, in which the bromine:
A. moves from one liquid layer to the other. b) Outline the process of “addition polymerisation”
B. changes colour from brown to purple. of ethene.
C. completely loses its colour.
D. changes from colourless to purple.
3. In the “cracking” of the alkane C20H42, the

molecule happened to break up into 4 pieces; c) Draw a structural formula for a section of a
1 molecule of ethene, one of octane, 1 of hexene, polyethene molecule containing 3 monomer units.
and another hydrocarbon molecule. The formula for
the 4th fragment would be:
A. C4H8 B. C6H12 C. C2H4 D. C3H8

10.
4. An “addition polymer” is formed when: A common plastic is known as P.V.C.
A. long-chain alkane molecules combine. a) Draw a structural formula for the monomer from
B. C= C double bonds are formed in monomer which PVC is made, and give both its common
molecules. name and systematic chemical name.
C. molecules join by removing atoms to create
bonds.
D. monomers join by splitting C= C double
bonds. b) Account for the differences in properties and
typical uses of PVC compared to polyethene.
5. In general terms, increasing the size and mass of
any “side groups” in an ethene-based plastic, will
probably result in the plastic being:
A. softer and more flexible. 11. H O-H
B. less soluble in water. The amino acid “Glycine” has
C. a better conductor of electricity. the following structure: H N C C
D. harder and more rigid. H H O
The condensation
6. Cellulose is: polymer “polyglycine” can be
A. an addition polymer of ethylene. formed by joining together many glycine molecules.
B. a condensation polymer of glucose.
C. an addition polymer of glucose. a) Use structural diagrams to show the 2 products
D. a monomer which can be polymerised. formed when two glycine monomers join together.
Longer Response Questions

7.
Using structural formulas, show the addition
reaction between ethene and hydrogen bromide
(HBr). Show the reactants and product(s).
You do not need to name any compounds.
b) Explain why this is called “condensation”
polymerisation.

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®
Answer Section
keep it simple science
6.
Worksheet 1 a) 2,2-dichloropropanoic acid
1.
a) 5 b) 4 c) 3 d) 8 e) 1 f) 6 b) 1,2,3-trimethylpentane
2. c) 1,1,1-tribromo-2-butyne
a) pentane d) 2-chloro-3-methylbutanal
b) butanoic acid e) 1,3-difluoro-2-methyl-2-propanol
c) hexanol
d) butyne
e) bromoethane Worksheet 2
3. 1.
a) a) C4H10 + 13/ O2 4CO2 + 5H2O
CH3 CH CH2 CH3 2
CH2 b) C3H4 + 4O2 3CO2 + 2H2O

CH3 2.
a) C2H6 + F2 C 2H 5F + HF
b) The longest carbon “backbone” has 5 carbons,
with a methyl side-branch on the 3rd. b) C6H14 + F2 C6H13F + HF
Correct name is “3-methylpentane”.
3. C4H8 + H2 C4H10
4.
2-methyl-2-propanol CH3 4.
a) C5H10 + Br2 C5H10Br2
CH3 C CH3 1,2-dibromopentane
OH b) C5H10 + Br2 C5H10Br2

2,3-dibromopentane
5.
a) Cl Tutorial Note: Markovnikov’s Rule can be expressed in
H
various ways, but its simplest form is that a hydrogen
CH3 CH C atom predominately attaches to the carbon atom which
already has the most hydrogens on it. In these cases it
O means that (predominately) the isomer formed will have
the extra hydrogen on the terminal carbon.
CH3
b) OH 5.
CH3 CH2 CH C C4H8 + H2O C4H9OH (2-butanol)
O 6.
C3H6 + HF C3H7F (2-fluoropropane)
c) F F
Worksheet 3
CH CH2 CH CH2 CH3 a) 4 b) covalent
F F c) chains d) double or triple
e) hydrocarbons f) homologous
g) alkanes, alkenes & alkynes
h) carbon atoms i) -ANE
CH3
d) j) single k) CnH2n+2
CH3 C CH l) insoluble m) low
C CH3
n) polar o) dispersion
p) increases q) similar
r) double C= C s) CnH2n
t) triple u) CnH2n-2
CH3
v) vaporise w) high
e) CH2 x) mixture y) fractions
z) fractional distillation aa) falls
CH3 CH2 CH C CH3 ab) condenses
O

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®
Answer Section
Worksheet 5
Worksheet 4 a) homologous b) CnH2n+1OH
1. C 2. B 3. A 4. D 5. C c) alcohols d) -OH
6. e) polar f) dipole
a) UV energy can split Cl2 to form 2 Cl• , “free- g) hydrogen h) higher
radicals”. These are highly reactive and may attack i) soluble j) solvents
CH4 as follows: k) polar & non-polar l) fuels
m) energy content n) addition
CH4 + Cl• CH3• + HCl o) water p) sulfuric acid
This forms another free-radical which might attack q) ethanol to ethene r) concentrated
Cl2, thus perpetuating a chain of reactions which s) dehydration t) glucose
(overall) substitute Cl for H atoms in the alkane. u) fermentation v) enzymes
w) yeast x) sugar/carbohydrate
CH3• + Cl2 CH3Cl + Cl• y) yeast z) 25
aa) anaerobic ab) about 15%
b) A molecule already substituted, may react again. ac) fractional distillation ad) 95%
This way, many different products may form. ae) sugar af) distillation
eg CH3Cl + Cl2 CH2Cl2 + HCl ag) vinegar ah) carbon dioxide & water
7. a) ai) heat given out when 1 mole of fuel is burned
100
completely
aj) standard states at standard conditions
Boiling Point (oC)
ak) exo-
al) negative am) positive
an) increases ao) alkane
ap) renewable aq) technology
0
ar) greenhouse, eco, as) 20%

at) cultivated for “ethanol farming”
au) distillation av) engines
-100
1 2 3 4 5 6 7 8
Worksheet 6
No. of Carbon Atoms 1.
b) butene -16oC The OH group contains a polar bond which creates
approx (listed value -6) pentene approx 25oC(listed value 30) an electric dipole on the molecule. Inter-molecular
(Errors probably due to the small graph scale) hydrogen bonding occurs, which results in higher
c) The only inter-molecular forces are weak mp & bp.
dispersion forces. Molecules are not held together 2.
strongly. For fermentation, a source of sugar (or other
carbohydrate) is needed, plus the presence of live
8. yeast cells. Temperatures near 25oC favour the
a) C6H14 + 19/ O2 6CO2 + 7H2O growth of the yeast and anaerobic conditions (no
2
oxygen) favours the formation of ethanol rather
b) C3H6 + H2O C3H7OH (propanol) than just CO2.
9. Glucose Ethanol + Carbon dioxide

a) Saturated hydrocarbons are the alkanes which C6H12O6(aq) 2 C2H5OH(aq) + 2 CO2(g)
have all single C- C bonds and the maximum
“saturation” with H atoms. 3.
Unsaturated refers to alkenes & alkynes, with a) C4H9OH + 6 O2 4CO2 + 5H2O
double & triple bonds & therefore, less than
maximum H atoms. b) Heat absorbed by calorimeter:
These words can also be applied to other Q = m.c.∆
∆T = 0.050 x 4,183 x 29 = 6,065 J ≅ 6.1 kJ
homologous series.
c) This is for 0.60g butanol, so energy = 10.1 kJ / g
b) Covalent bonds are arranged at the points of a MM = 74, so ∆Hc = 747 kJmol-1.
tetrahedron around a C atom and therefore, This is very inaccurate because most of the heat
molecules have 3D geometry. released is NOT captured & measured by the
A double bond is rigid (no rotation) and forces the primitive calorimeter.
H atoms (on the carbons which are double-bonded)
into a 2D flat plane around the carbons. d) Reliability can still be achieved if all parameters
The triple bond is rigid and allows only 1 other are kept constant from one measurement to the
bond on each C atom involved. This bond is forced next. eg same distance from burner to can, same
into the same 1-D line as the triple bond. time of burning, same degree of wind protection
eg ethyne is a linear molecule. and so on.

lOMoARcPSD|16722454
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Answer Section
Worksheet 8
Worksheet 6 (cont.) 1. Names of Esters
4. a) ethyl propanoate b) propyl ethanoate
a) 1-chlorobutane Cl CH2 CH2 CH2 CH3
c) pentyl methanoate d) methyl pentanoate
e) butyl hexanoate f) octyl ethanoate
b) 2-chlorobutane Cl
CH3 CH CH2 CH3 2. Condensed Structural Formulas

a) i) CH3CH2OH ii) CH3CH2COOH
iii) CH3CH2COOCH2CH3
5. Reaction occurs when ethanol is treated with a b) i) CH3CH2CH2OH ii) CH3COOH
conc.sulfuric acid catalyst. The concentrated acid iii) CH3COO(CH2)2CH3
has a great affinity for water and chemically c) i) CH3(CH2)3CH2OH ii) HCOOH
extracts it from ethanol, forming ethene. iii) HCOO(CH2)4CH3
d) i) CH3OH ii) CH3(CH2)3COOH
ethanol ethene + water iii) CH3(CH2)3COOCH3
e) i) CH3(CH2)2CH2OH ii) CH3(CH2)4COOH
6. iii) CH3(CH2)4COO(CH2)3CH3
1o alcohols oxidise firstly to aldehydes, then (with f)i) CH3(CH2)6CH2OH ii) CH3COOH
more heat and reflux) to a carboxylic acid. iii) CH3COO(CH2)7CH3
2o alcohols oxidise to the corresponding ketone.
3o alcohols do NOT oxidise. 3. Names from Structures
a) butyl methanoate. butanol + methanoic acid
7.a) b) butyl propanoate. butanol + propanoic acid
It can be made by fermentation from plant c) pentyl pentanoate. pentanol + pentanoic acid
carbohydrates (eg sugar) which can be grown over d) methyl pentanoate. methanol + pentanoic acid
& over and never run out. e) heptyl hexanoate. heptanol + hexanoic acid.
b)
The CO2 released when the ethanol is burned is
exactly the same as that absorbed by the plant
Worksheet 9
1.
during growth. Therefore, using ethanol fuel should a) It is a hydrocarbon chain of 12 to 24 carbons,
NOT add extra CO2 to the atmosphere. with a COOH acid group at one end.
c) H
b)Structural formula for glycerol
Probably not, because our transport and the large H C O H
energy input for distillation, still come largely from c) Triglyceride is a molecule of
fossil fuels. glycerol linked to 3 fatty acids. H C O H
d)
Schematically: H C O H
Vast areas of food production land would need to
be allocated to growing crops to make ethanol. This H
could create a food supply crisis.
3 fatty acids
Worksheet 7
Glycerol
a) alcohols b) -OH
c) CnH2n+1OH d) polar
e) hydrogen f) alkanes
g) COOH h) hydrogen
i) m.p. & b.p. is even higher than Triglycerides (fats & oils) are esters because they
are the product of a condensation reaction between
j) alkanols with alkanoic acids
a carboxylic acid & an alcohol.
k) water l) alkanol
m) -yl n) alkanoic acid 2.
o) -oate p) reflux a) Saponification
q) pressure / vapours r) condensed fat + sodium hydroxide soap + glycerol
s) reflux condenser t) Sulfuric acid
u) equilibrium v) odours and tastes b) Simply add oil to a strong base solution and heat
w) fruits x) fats and oils gently. Cooling and adding salt will help separate
y) artificial flavourings z) solvents the soap from the water phase.
aa) shampoo/cosmetics/plastics

lOMoARcPSD|16722454
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Answer Section
Worksheet 9 (cont.) Worksheet 11
1.
3.
a) An emulsion is a stable mixture containing 2 The empirical formula matches with propanol
normally immiscible liquids. An emulsifier acts to C3H7OH and also matches with the molar mass.
keep one of the liquids dispersed in the other, as
tiny, separate droplets. It could be 1-propanol or 2-propanol.
b) “Dirt” often contains fat/oil so it will not simply CH3 CH CH3

wash away in water. Emulsifiers like soap can CH3 CH2 CH2 OH
emulsify the fat, so that it becomes suspended in OH
water and washes away. 2.
Each droplet of fat becomes C3H7OH + HCl C3H7Cl + H2O
c) surrounded by soap molecules.
These suspend each droplet in the
water and prevent droplets joining Applying Markovnikov’s Rule suggests that the
together
predominate product (probably about 90%) would
Fat Fat
be 2-chloropropane. This will be the case no matter
Water which isomer of propane you begin with.
Water
3
Water a) It hints at the formation of an ester.
Fat
b) Q-2 must be a carboxylic acid. Since it came

from the oxidation of propanol, it must be
4.
propanoic acid.
a) Both soap and the most common detergents are
long-chain hydrocarbons with a negative ionic
group on one end. The hydrocarbon is non-polar c) Only a primary alcohol can be oxidised to
and hydrophobic, while the ion is hydrophilic. carboxylic acid. (2o alcohols give ketones)
Therefore, the stating chemical was 1-propanol and
b) Soap does not work in “hard water” because the NOT 2-propanol.
calcium salt of the fatty acid is insoluble and forms
a greasy scum. Detergents continue to work d)
perfectly as emulsifiers because the ions remain propanoic acid + propanol propylpropanoate
soluble in the presence of Ca2+ ions. + water
e)
Worksheet 10 i) it acts as an oxidising agent.
1. ii) propanal
a) R-COOH + H2O R-COO- + H3O+
4. dehydration reaction
b) acid base conj.base conj.acid conc. H2SO4
CH3 CH2 CH2 OH CH3 CH CH2

2.
a) butanoate ion
b) methanoate ion +H2O
c) octanoate ion propanol propene + water
3. Reaction with bromine:

a) R-NH2 + H2O R-NH3+ + OH-
CH3 CH CH2 CH3 CH CH2
+ Br2
b) base acid conj.acid conj.base Br Br
4. propene + bromine 1,2-dibromopropane

a) butylammonium ion
b) dimethylammonium ion
c) octylammonium ion

lOMoARcPSD|16722454
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Answer Section
9.
Worksheet 12 a) “Cat-cracking” refers to catalytic cracking; the
a) fuels b) petrochemicals use of a catalyst to break long chain hydrocarbons
c) ethene d) double into smaller molecules.
e) reactive f) addition
g) bromine h) de-colourised b) The double C= C bond in ethylene molecules
i) cracking j) heat or catalysts allows thousands of them to undergo addition
k) octane l) gas reactions with each other. They join in very long
m) polymers/polythene n) addition chains of polyethene.
o) polyethene p) pressure & temperature
H H H H H H
q) low r) side-branches
s) flexible t) cling-wrap c) C C C C C C
u) catalyst v) pack together
w) high x) tough plastic carry bags H H H H H H
y) polyvinyl chloride z) vinyl chloride
aa) chloroethene ab) dispersion 10. H H
ac) harder ad) rigid a) Common name = vinyl chloride C C
ae) drain pipes & gutters af) styrene Systematic = chloroethene H Cl
ag) ethenylbenzene ah) benzene
ai) dispersion aj) hard and rigid b) Compared to polyethylene, PVC has one chlorine
ak) condensation al) water molecule atom in place of a hydrogen on each monomer unit.
am) polyesters an) proteins & starch/DNA This greatly increases the molecular weight, and
ao) cellulose ap) glucose therefore the dispersion forces between PVC
aq) wall ar) cotton & linen molecules. The PVC molecules “stick” together
as) rayon at) glucose much more strongly, making the plastic harder and
au) ethanol av) ethene more rigid.
aw) glucose ax) PHB
ay) Bacillus magaterium While its properties make polyethylene suitable for
az) Genetic Engineering cling-wrap film, the tougher PVC is used for
ba) corn drainage pipes and guttering.
11.
a) H O-H O-H
Worksheet 13 H
1. B 2. C 3. A 4. D 5.D 6. B N C C H
H H O water
7.
H N C C 2 glycine
H Br molecules
H H H H O joined
C C + HBr H C C H
H H H H b) as each pair of glycines join together, a molecule
of water is formed. The appearance of water is
8. termed “condensation”.
Hexene will undergo an addition reaction across
the C= C double bond.
Br Br
CH2= CH-(CH2)3-CH3 + Br2 CH2-CH-(CH2)3-CH3
The Br2 is consumed and its colour disappears.
Hexane has no double C= C bond, so does not

react.

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KISS Resources for NSW Syllabuses & Australian Curriculum

® KEEP IT SIMPLE SCIENCE

e) C2H5Br ....................................................... e) 3-ethyl-2-hexanone

KISS Resources for NSW Syllabuses & Australian Curriculum

2. a single substitution reaction between F2 and:

3. the addition reaction between H2 and butene.

Worksheet 3 About the Hydrocarbons

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® Worksheet 4 Practice Questions

Boiling Point (oC)

3. Which of the following is NOT a property of the

5. The reaction between 2-hexene and Br2 would

Longer Response Questions

b) differences in the geometry of hydrogen atoms

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KISS Resources for NSW Syllabuses & Australian Curriculum

® Worksheet 5 The Alcohols

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KISS Resources for NSW Syllabuses & Australian Curriculum

® Worksheet 6 Alcohols Again

a) Write a balanced equation for this combustion.

b) Calculate the “heat of combustion” from this

c) The listed value of ∆Hc = 2676 kJmol-1.

c) Is it actually “carbon-neutral” with current

d) Suggest ways to improve the reliability of the

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KISS Resources for NSW Syllabuses & Australian Curriculum

Worksheet 8 More Esters

c) pentanol & methanoic acid e) i)

3. Names from Structures

The first has been done for you as an example.

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KISS Resources for NSW Syllabuses & Australian Curriculum

® Worksheet 9 Fats, Oils, Soap, Detergents

b) Explain how emulsification results in cleaning

c) Explain, with the aid of simple diagrams, how

b) performance as emulsifiers in “hard water”.

Worksheet 10 Organic Acids & Bases

b) Identify the B-L acid and B-L base in the reaction

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® Worksheet 11 Reaction Pathways

All organic compounds should be named.

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® Worksheet 13 Practice Test-Style Questions

2. Alkenes can be identified by their reaction with

3. In the “cracking” of the alkane C20H42, the

A. C4H8 B. C6H12 C. C2H4 D. C3H8

Longer Response Questions

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CH2 b) C3H4 + 4O2 3CO2 + 2H2O

OH b) C5H10 + Br2 C5H10Br2

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