2016 Organic Molecules LRG Answers (CAPS Aligned Manual Development) 2016-05-22

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Learner Revision Guide Answers

Grade 12

PHYSICAL SCIENCES:
Organic Molecules
Contents
Activity 1: Structure of organic compounds 3
Activity 2: Physical properties of organic compounds 10
Activity 3: Organic reactions..................... 16
Activity 4: Polimerisation Reactions ........ 22
3. Summative Task .................................. 23

PHYSICAL SCIENCES: ORGANIC MOLECULES 2


Activity 1: Structure of organic
compounds

QUESTION 1

1.1 Alcohols
1.2 Ketones
1.3 Ethene
1.4 Haloalkanes
1.5 Hydrocarbons
1.6 Alkynes
1.7 Methanal
1.8 Functional group
1.9 Ethyne
1.10 Propanone/propan-1-one/1-propanone
1.11 Ketones
1.12 Functional group
1.13 Alkynes
1.14 Haloalkanes
1.15 Structural isomers

QUESTION 2

2.1 D 2.2 A 2.3 B 2.4 C


2.5 A 2.6 B 2.7 B 2.8 C
2.9 C 2.10 A 2.11 B 2.12 B
2.13 C 2.14 D 2.15 B 2.16 B
2.17 A 2.18 C 2.19 B 2.20 C
2.21 A 2.22 D 2.23 D

QUESTION 3

3.1 Alkenes

3.2
H H H H
C C + Cl Cl H C C H
H H Cl Cl

PHYSICAL SCIENCES: ORGANIC MOLECULES 3


3.3 4,4-dimethylhexan-2-one/4,4-dimethyl-2-hexanone

3.4
H H
H C H H C H
H H H H H H

H C C C C H H C C C C H

H H H H H H
H C H H C H
H H

QUESTION 4

4.1
4.1.1 A 4.1.2 D&F 4.1.3 D
4.1.4 E 4.1.5 B

4.2
4.2.1 2-methylbut-1-ene

4.2.2
H H H H O

H C C C C C O H
H H H H

4.3
4.3.1 Pleasant odour

4.3.2 Ethanol

4.3.3 Ethyl propanoate

QUESTION 5

5.1
5.1.1 C

5.1.2 D

PHYSICAL SCIENCES: ORGANIC MOLECULES 4


5.2
5.2.1 4-methylpentanal

5.2.2 Propyne/prop-1-yne/1-propyne

5.2.3 2,4-dimethylhexane

5.3 H2O/water
CO2/carbon dioxide

5.4
5.4.1 Ethanol
O
5.4.2
C O H

5.4.3 Butanoic acid

5.4.4
H H O H H H
H C C O C C C C H
H H H H H

QUESTION 6

6.1
6.1.1 A 6.1.2 D

6.2
6.2.1 1-bromo-2-methylpropane

6.2.2 2,4-dimethylhexane
6.3
O
H C H

6.4 Ethanoic acid

PHYSICAL SCIENCES: ORGANIC MOLECULES 5


6.5
H O
H C O C H

QUESTION 7

7.1
7.1.1 E 7.1.2 A 7.1.3 A
7.1.4 F 7.1.5 A&D 7.1.6 C

7.2
7.2.1
H H H
H C C C C C H
H H H H H

7.2.2
H
H C H

H H H H H H

H C C C C C C C H

H H H H H H
H C H
H

7.3
7.3.1 Carbonyl (group)

7.3.2 2-methylpropan-1-ol/2-methyl-1-propanol

PHYSICAL SCIENCES: ORGANIC MOLECULES 6


QUESTION 8

8.1
8.1.1 O

C H

8.1.2 Ketones

8.1.3
H H H O
H C C C C H
H H H

8.1.4 2,5-dimethylhex-3-ene/2,5-dimethyl-3-hexene

8.2 Tertiary

QUESTION 9

9.1
9.1.1 Ketones

9.1.2 3,5-dichloro-4-methyloctane

9.1.3
H
H C H
H H

H C C C H

H O H

H
9.2
9.2.1 Acts as catalyst./Increases the rate of reaction./Act as dehydrating agent

9.2.2 Water/H2O

9.2.3 Answer: mol C : mol H : mol O

PHYSICAL SCIENCES: ORGANIC MOLECULES 7


40 6,67 53,33
: :
12 1 16
3,33 : 6,67 : 3,33
1 : 2 : 1
Empirical formula: CH2O

9.2.4 Answer: M(CH2O) = 30 g·mol-1


Formula-units:
60
 2 30
30
Molecular formula: C2H4O2

9.2.5
O
H C O H
9.2.6 Methyl methanoate

QUESTION 10

10.1
10.1.1 B

10.1.2
O

C H

10.1.3 CnH2n-2
10.1.4 4-ethyl-5-methylhept-2-yne / 4-ethyl-5-methyl-2-heptyne

10.1.5 2-methylpropane

10.2
10.2.1 Alkanes

10.2.2 Methylpropane
H
H C H
H H
H C C C H
H H H
10.2.3 Chain

PHYSICAL SCIENCES: ORGANIC MOLECULES 8


10.3
10.3.1 Haloalkanes

10.3.2 Substitution / halogenation / bromonation

PHYSICAL SCIENCES: ORGANIC MOLECULES 9


Activity 2: Physical properties of organic
compounds

QUESTION 1

1.1 Boiling point

1.2 Vapour pressure

1.3 Intermolecular forces

1.4 London forces/dispersion forces

QUESTION 2

2.1 B 2.2 D 2.3 D 2.4 A


2.5 A

QUESTION 3

3.1
3.1.1 An organic compound/substance which consists of carbon and hydrogen atoms only.

3.1.2 C5H12

3.1.3 Speeds up the reaction/Increase reaction rate.


Reaction runs at a lower temperature/energy.
Cost is reduced/better safety.

3.1.4
H H H
H C C C C
H H H
H C H
H

3.1.5 Addition/hydrogenation

PHYSICAL SCIENCES: ORGANIC MOLECULES 10


QUESTION 4

4.1 Compounds have the same molecular formula, but different structural formulae.

4.2 From A to C:
Boiling points decrease from A to C.
 Branching increases./Molecules become more compact./Molecules become more
spherical./Decrease in surface area (over which the intermolecular forces act.)
 Decrease in (strength) of intermolecular forces.
 Less energy needed to overcome intermolecular forces.

4.3 Branched chains have weaker intermolecular forces, therefore they (burn) react
faster.
OR
Branched chains have higher vapour pressures.

QUESTION 5

5.1
5.1.1 Fuels

5.1.2 CnH2n+2

5.2
5.2.1 Boiling point

5.2.2 Chain length/Molecular size/Molecular mass

5.2.3 Criteria for conclusion:


- Dependent and independent variables correctly identified.
- Relationship between the independent and dependent variables correctly stated.
Examples:
• Boiling point increases with increase in chain length/molecular size/molecular
mass.
• Boiling point decreases with decrease in chain length/ molecular size/molecular
mass.
• Boiling point is proportional to chain length/molecular size/molecular mass.

5.3 Pentane and hexane

5.4 C3H8 + 5O2 → 3CO2 + 4H2O

PHYSICAL SCIENCES: ORGANIC MOLECULES 11


5.5 Lower than
 Structure:
Isomers have more branching/ more compact or spherical molecules / smaller
surface areas over which the intermolecular forces act.
 Intermolecular forces:
Weaker intermolecular forces/less intermolecular forces
 Energy:
Less energy needed to overcome intermolecular forces.

QUESTION 6

6.1
6.1.1 Gas
Boiling point lower than room temperature./lower than 25 °C.

6.1.2 Lower than


Isomers of A:
 More branching/Molecules more compact./Smaller surface area (over which the
intermolecular forces act.)
 Weaker/less intermolecular forces.
 Less energy needed to overcome intermolecular forces.

6.1.3 2C4H10 + 13O2 → 8CO2 + 10H2O

6.1.4 Compound B contains a carbonyl group/O atom (bonded to C atom) and is a polar
(molecule)/dipole. In addition to London forces, there are also dipole-dipole forces
between molecules.
Compound A is an alkane and is non-polar and has only London forces between
molecules. Intermolecular forces in A are weaker than those in B.

6.2
6.2.1 Both compounds have hydrogen bonding (between molecules.)
Compound D: Two sites for hydrogen bonding/forms dimers/is more polar than
compound C with only one site for hydrogen bonding
Intermolecular forces in compound D stronger than those in compound C.

6.2.2 (Compound) C
Lowest boiling point

PHYSICAL SCIENCES: ORGANIC MOLECULES 12


QUESTION 7

7.1 Structural isomers

7.2
7.2.1 Boiling point

7.2.2 Branching

7.2.3 Number of C atoms/Molecular mass/molar mass

7.3 Saturated
No carbon-carbon double (or triple) bonds./Only single bonds between C atoms./No
multiple bonds.

7.4
7.4.1 A

7.4.2 Pentane

7.5
7.5.1
H
H C H
H H

H C C C H

H H

H C H
H

7.5.2 Most branching / Molecules most compact or spherical/Smallest surface area over
which intermolecular forces act.
Least/weakest intermolecular forces.
Least energy needed to overcome intermolecular forces.

7.6 C
Lowest boiling point

PHYSICAL SCIENCES: ORGANIC MOLECULES 13


QUESTION 8

8.1 Saturated/Versadig
B/It has ONLY single bonds.//It has single bonds between C atoms. /B/It has no
double OR triple bonds OR multiple bonds. /B/It contains the maximum number of H
atoms bonded to C atoms. /Each C atom in B is bonded to four other atoms.

8.2
8.2.1 - 42 °C

8.2.2 78 °C

8.3 Between molecules of C/propane are London forces/dispersion forces/ induced


dipole forces.
 Between molecules of E/ethanol are (London forces/dispersion forces/ induced
dipole forces and) hydrogen bonds.
 Hydrogen bonds/Forces between alcohol molecules are stronger.

8.4 Decrease
From A to D:
 Chain length/molecular mass/molecular size/surface area increases.
 Strength of intermolecular forces/ London forces/dispersion forces/induced
dipole forces increases.
 More energy needed to overcome/break the intermolecular forces.

8.5 Higher than

QUESTION 9

9.1 A bond/an atom or a group of atoms that determine(s) the (physical and chemical)
properties of a group of organic compounds.
9.2
9.2.1 D
Lowest vapour pressure

9.2.2 A

9.3 • Between molecules of A / butane / alkanes are London / induced dipole /


dispersion forces.
• Between molecules of B / propan-2-one / ketones are dipole-dipole
forces in addition to London / induced dipole / dispersion forces.
• Intermolecular forces in A are weaker than those in B. / Less energy is needed in

PHYSICAL SCIENCES: ORGANIC MOLECULES 14


A to break/overcome intermolecular forces.

9.4 Hydrogen bonding

9.5 D has more sites for hydrogen bonding than C / forms dimers / is more polar than C.
 D has stronger / more intermolecular forces / dipole-dipole forces.
OR D needs more energy to overcome/break the intermolecular forces.

9.6 C4H10 O2 CO2 H2O


Initial V (cm3)/BeginV (cm3) 8 60 0 0
Change in V (cm3)/Verandering V (cm3) 8 52 32 40
Final V (cm3)/Finale V (cm3) 0 8 32 40

Total volume = 8 + 32 + 40 = 80 cm3

QUESTION 10

10.1 High energy of combustion. / Combustion releases huge amounts of energy. / Highly
exothermic.
10.2 Boiling point increases with number of carbon atoms.

10.4 London forces between alcohol molecules increase with increase in molecular size

10.5 Hydrogen bonds between alcohol molecules are stronger than London forces
between molecules of alkanes.

10.6 Petrol has a low boiling point, vapourises easily/is volatile/explosive/flammable/easily


combustible/vapours have a higher density than oxygen and when swallowed vapours
can cause suffocation.

10.7 Ethanol can be produced by fermentation of plant material e.g. maize and sugar cane.
Alkanes are fossil fuels which are non-renewable.

PHYSICAL SCIENCES: ORGANIC MOLECULES 15


Activity 3: Organic reactions

QUESTION 1

1.1 Hydrohalogenation
1.2 Esterification
1.3 Cracking
1.4 Cracking
1.5 Hydrohalogenation
1.6 Dehydrohalogenation
1.7 Hydration
1.8 Dehydration
1.9 Halogenation

QUESTION 2

2.1 C 2.2 C 2.3 D 2.4 A


2.5 A 2.6 C 2.7 C 2.8 C
2.9 B

QUESTION 3

3.1
3.1.1 Substitution/Halogenation/Chlorination
3.1.2 Substitution/Hydrolysis

3.2
3.2.1 Hydrogenation
3.2.2
H H H H H
C C C H +H H H C C C H
H H H H H H

3.3
H H H
H C C C H
H H Cl

3.4
3.4.1 Mild heat and dilute base or water
PHYSICAL SCIENCES: ORGANIC MOLECULES 16
3.4.2 NaOH/KOH/H2O

3.5
3.5.1 Esterification
3.5.2 Concentrated H2SO4/Concentrated sulphuric acid
3.5.3
H H H O H

H C C C O C C H

H H H H

3.5.4 Propyl ethanoate

3.6 Sulphuric acid / H2SO4 / Phosphoric acid / H3PO4

QUESTION 4

4.1 Alcohols
4.2
H H H O H H O H
H C C O + H C C O H C C O C C H + H O
H H H H H H H H H

4.3 Catalyst/Dehydrating agent


4.4 Ethanol is flammable.
4.5 Vapours are cooled down and condense / return to the test tube./
It prevents vapours from leaving the test tube./It functions as a condenser./It causes
the mixture to reflux.
4.6 Sodium carbonate solution is a base and will neutralise both acids, preventing them
from masking the smell of the ester.
4.7 Vapour pressure / Boiling point / Volatility

QUESTION 5

5.1
H H
C C
H H

5.2 The ethene liberated by the banana ages the cabbage and lettuce.
5.3
5.3.1 CnH2n
PHYSICAL SCIENCES: ORGANIC MOLECULES 17
5.3.2 A: substitution/halogenation/bromination
B: addition/hydrogenation
D: addition/hydration
H: substitution/halogenation/bromination

5.3.3
H H H H
Pt
C C + H H H C C H
H H H H
ethene ethane

5.3.4 HBr OR NaBr + H2SO4

5.3.5
(a) Base in E is a concentrated base in ethanol
Base in G is a dilute in water
(b) Dehydrohalogenation/dehydrobromination

QUESTION 6

6.1
6.1.1 Hydrolysis
6.1.2 Mild heat
Dilute strong base/aqueous base
6.1.3 Ethanol

6.2
6.2.1 Esterification
6.2.2
O

H C O H

6.2.3 Ethyl methanoate

QUESTION 7

7.1
7.1.1 Esterification
7.1.2
O

C O C

PHYSICAL SCIENCES: ORGANIC MOLECULES 18


7.1.3 Propanoic acid

7.1.4 Dehydration/elimination

7.1.5 (Concentrated) H2SO4 / sulphuric acid / H3PO4 / phosphoric acid

7.1.6
H H
C C
H H

QUESTION 8

8.1 An (organic) compound that consists of hydrogen and carbon atoms only.

8.2 CO2 & H2O

8.3
H H
H C H H C H
H H H

H C C C C C H

H H H H

H C H
H

8.4
H H H
H C C C
H H
prop-1-ene

PHYSICAL SCIENCES: ORGANIC MOLECULES 19


QUESTION 9

9.1 Chlorination/Halogenation/Substitution

9.2 H H
H C C H

H Cℓ

9.3 HCℓ

9.4 Chloroethane

QUESTION 10

10.1 Heat OR light

10.2 Bromination/Halogenation/Substitution

10.3
H Br Br Br
H C Br H C Br Br C Br Br C Br
H H H Br
bromomethane dibromomethane tribromomethane tetrabromomethane

QUESTION 11

11.1 It contains a double bond/C = C between two carbon atoms./All carbon atoms not
bonded to the maximum number of atoms /four atoms.

11.2
11.2.1 Addition

11.2.2 Substitution

11.3
H H H

H C C C H

Cl Cl H

PHYSICAL SCIENCES: ORGANIC MOLECULES 20


11.4 Heat/sunlight/ultraviolet light/hf

11.5 Butane

11.6 Hydrogen chloride/HCℓ

11.7
11.7.1 Elimination

11.7.2 But-2-ene

11.7.3
H
H H Cℓ H H H O H
H C C C C H + NaOH H C C C C H + NaCℓ
H H H H H H H H

11.7.4 Hydrolysis

QUESTION 12

12.1
12.1.1 Haloalkanes/Alkylhalides

12.1.2

H H H H H
C C C H + Br2 H C C C H
H H H Br Br H

12.1.3 Addition

12.2 H H H

H C C C H

H Br H

12.3
12.3.1 Dilute strong base
Mild heat

12.3.2 Secondary

PHYSICAL SCIENCES: ORGANIC MOLECULES 21


12.3.3 Hydrolysis

12.4
12.4.1 Sulphuric acid/H2SO4/phosphoric acid/H3PO4

12.4.2 Dehydration

Activity 4: Polimerisation Reactions

1.
1.1 Small organic molecules that can be covalently bonded to each other in a repeating
pattern.

1.2
1.2.1
H H
C C
H H

1.2.2 Addition

2.
2.1
2.2.1
H H
C C
H H

2.2.2
H H O H O

H O C C O H H O C C C O H

H H H

2.2 A: Addition
B: Condensation
2.3 B; H2O

PHYSICAL SCIENCES: ORGANIC MOLECULES 22


3. Summative Task

QUESTION 1: Multiple choice questions

1.1 B (2)

1.2 B (2)

1.3 D (2)

QUESTION 2

2.1 Temperature at which the vapour pressure equals atmospheric pressure.  (2)

2.2 The stronger the intermolecular forces, the higher the boiling point./The boiling
point is proportional to the strength of intermolecular forces.  (1)

2.3
2.3.1
 In A/propane/alkanes: London forces/dispersion forces/induced dipole forces. 
 In B/ propan-2-one/ketones: dipole-dipole forces in addition to London
forces/dispersion forces/induced dipole forces. 
 Intermolecular forces in A are weaker than in B./Intermolecular forces in B are
stronger than in A./London forces are weaker than dipole-dipole forces.  (3)

2.3.2 Both C and D: hydrogen bonding 


D has two/more sites for hydrogen bonding./D forms dimers./D is more polar./C has
one/less sites for hydrogen bonding. 
D has stronger intermolecular forces than C./C has weaker intermolecular forces than
D.  (3)

2.4 Liquid  (1)


[10]

Question 3

3.1
3.1.1 B  (1)

3.1.2 E  (1)

PHYSICAL SCIENCES: ORGANIC MOLECULES 23


3.1.3 A  (1)

3.2
3.2.1 4-chloro-2,5-dimethylheptaneB (3)

3.2.2 2-methylpropan-1-ol  (2)

3.2.3 O

C C C
(1)

3.3
3.3.1 Compounds with the same molecular formula but different positions of the functional
groups /side chain/substituents on parent chain.  (2)
3.3.2 But-1-ene  & But-2-ene  (4)

3.3.3 Write down the structural formula of a chain isomer of compound C. (2)
Answer:
H

H C H H

H C C C H

H  H

3.4
3.4.1 Cracking / Elimination  (1)

3.4.2 Ethene  (1)

3.4.3 C4H10  (1)

3.4.4 Polyethene  
H H
C C
H H n
(3)
[23]
QUESTION 4

4.1
4.1.1 Addition  (1)

4.1.2 Polyethene  (1)


PHYSICAL SCIENCES: ORGANIC MOLECULES 24
4.2
4.2.1 Chloroethane  (2)

4.2.2 Hydrohalogenation/Hydrochloronation  (1)

4.3
4.3.1
H H
H C C O H 
H H (2)

4.3.2 HCℓ/hydrogen chloride  (1)

4.4
4.4.1 Saturated 
There are no double/multiple bonds between C atoms./Carbon atoms are bonded to the
maximum number of H atoms.  (2)

4.4.2 H2/Hydrogen gas  (1)

4.4.3 2C2H6 + 7O2 → 4CO2 + 6H2O  Bal.  (3)


[14]

GRAND TOTAL: 53

PHYSICAL SCIENCES: ORGANIC MOLECULES 25

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