ORGANIC CHEMISTRY NOTES
&
Past Papers
AS- REVISION
NAME:_________________________________________
Zafar Iqbal Ch.
ALKANE
ALKENE
ALCOHOL
ALDEHYDE
KETONE
Carboxylic
Acid
Pg-1
complete
incomplete
combustion
Alkanes
Free radical substitution
Sunlight
x2
x2
x2
x2
Zafar Iqbal Ch.
Pg-2
Preparation of Alkene
1- By the ________________________________of Alkane
2- By the ______________________________________of Haloalkane
3- By the ______________________________________of Alcohol
Spider diagram of Alkene
Addition Polymerization
Cold dilute KMnO 4/H+
HX /heat
Room temp.
Alkene
X2/CCl4
Room temp.
Dark
Aq.Bromine
Hot & conc.KMnO 4/H+
H2
Ni/Pt
180 oC
Excess
Combustion.
H2O(g) 300oC +
H3PO4 60-70 atm
Limited
O2
O2
H2O(l)/H2SO4
ZAFA
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CH.
Pg-3
1.
hot concentrated
MnO4– / H+
CH3CH
CHCH3
Cl 2
cold dilute
MnO4– / H+
A
B
C
K2Cr2O7 / H
+
ZAFA
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CH.
D
[4]
Pg-4
2.
Crude oil is the principal source of hydrocarbons. The following are examples of such
hydrocarbons.
H
H
H
C
C
H
H
H
H
H
ethane
C
C
CH3
H
propene
cyclohexene
(a) Give the structural formulae of the organic products in the following reactions.
(i)
The reaction of ethane with bromine in the presence of u.v. light.
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CH.
(ii)
The polymerisation of propene.
(iii)
The oxidation of propene with cold, acidified potassium manganate(VII).
(iv)
The reaction of cyclohexene with hydrogen bromide.
(v)
The reaction of cyclohexene with hot acidified potassium manganate(VII).
[5]
Pg-5
HX
Sunlight
HX
Room temp.
PX3 ,PX 5 , SOX 2
X2
NaOH/KOH
Ethanol (heat + reflux)
Limited
NH3 ethanolic
Haloalkane
ZAFA
R-X
NaOH/KOH
Aqueous/Heat + Refulux
KCN/NaCN
R IQ
BAL
CH.
Heat + reflux
LiAlH4 in dry ether
or H 2 (Pt/Ni)
Reduction
R-X
Hydrolysis
H3O+
R-X
OH-
Pg-6
3.
Complete the following reaction scheme which starts with propene.
In each empty box, write the structural formula of the organic compound that would
be formed.
Br2
CH3CH=CH2
KMnO4 /H+
cold, dilute
A
B
ZAFA
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CH.
D
HBr
KCN in
NH3
aqueous
ethanol
in an excess
C
NaOH(in ethanol)
heat under
reflux
H2SO4(aq)
heat under
reflux
E
F
G
[7]
Pg-7
Hydroxy Compounds.
Distilled off
o
P alcohol
HEAT+ REFLUX
Soalcohol
oxidation
Toalcohol
PX3,PX5,SOX2
Chemical Properties of alcohol.
HX
Reactive metal
170oC
Conc.H2SO4
Complete
Combustion
Carboxylic acid
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CH.
Pg-8
4.
Crotyl alcohol, CH3CH=CHCH2OH, is a colourless liquid which is used as a solvent.
In the boxes below, write the structural formula of the organic compound formed when
crotyl alcohol is reacted separately with each reagent under suitable conditions.
If you think no reaction occurs, write 'NO REACTION' in the box.
A
Br2 in an inert organic
solvent
B
PCl 5
C
H2 and Ni catalyst
D
NaBH4
E
K2Cr2O7 / H+
heat under reflux
[5]
ZAFA
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CH.
Pg-9
5.
A series of reactions based on propan-1-ol is shown.
CH3CH2CH2OH
reaction 1
steam
CH3CH=CH2
reaction 2
catalyst
reaction 3
U (C3H8O)
HBr
V
CH3CH2CO2H
(a) Suggest a suitable reagent and conditions for reaction 1.
.............................................................................................................................................. [2]
(b) (i) Write an equation for reaction 2, using [O] to represent the oxidising agent.
....................................................................................................................................... [1]
(ii) Suggest a suitable reagent and conditions for reaction 2.
....................................................................................................................................... [2]
(c) Give the structural formulae of U and V.
U ................................................................................................................................................
V ................................................................................................................................................
[2]
(d) Suggest a suitable reagent and conditions for reaction 3.
....................................................................................................................................................
.............................................................................................................................................. [2]
[Total: 9]
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CH.
Pg-10
6.
Compounds containing the allyl group, CH2=CHCH2–, have pungent smells and are found in
onions and garlic.
Allyl alcohol, CH2=CHCH2OH, is a colourless liquid which is soluble in water.
(a) Allyl alcohol behaves as a primary alcohol and as an alkene.
Give the structural formula of the organic compound formed when allyl alcohol is reacted
separately with each of the following reagents.
(i) acidified potassium dichromate(VI), heating under reflux
(ii) bromine in an inert organic solvent
(iii) cold, dilute, acidified potassium manganate(VII)
(iv) hot, concentrated, acidified potassium manganate(VII)
[5]
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CH.
Pg-11
7.
Food additives are substances added to food to preserve the flavour or to improve its taste
and appearance.
European Union legislation requires most additives used in foods to be labelled clearly in the
list of ingredients, either by name or by an ‘E number’. E296 is malic acid which occurs in
unripe fruit.
Malic acid has the structural formula HO2CCH2CH(OH)CO2H.
(a) Some reactions of malic acid are shown below.
In the boxes below, give the structural formulae of organic compounds A to F.
heat with
CH3OH / H+
HO2CCH2CH(OH)CO2H
heat with
CH3CO2H / H+
concentrated
H2SO4
A
B
C
hot concentrated
MnO4– / H+
steam / H3PO4
cold dilute
MnO4– / H+
D
E
F
[6]
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CH.
Pg-12
Carbonyl Compounds.
ALDEHYDE
Oxidation
Reduction
Chemical Properties of Aldehyde
HCN
-
reduction
H3O+
OH
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CH.
Pg-13
8.
hot concentrated
MnO4– / H+
CH3CH
CHCH3
Cl 2
cold dilute
MnO4– / H+
A
B
C
K2Cr2O7 / H+
D
ZAFA
[4]
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BAL
CH.
9.
Lactic acid may be synthesised from ethanol by the following route.
CH3CH2OH
step 1
CH3CHO
step 2
CH3CH(OH)CN
step 3
CH3CH(OH)CO2H
Give the reagent(s) and essential condition(s) for each step.
reagent(s)
condition(s)
step 1
step 2
step 3
[6]
Pg-15
Carbonyl Compounds.
KETONE
Reduction
HCN
OH-
H3O+
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CH.
reduction
Chemical Properties of Ketones
Pg-16
10.
Complete the following reaction scheme which starts with propanone.
In each empty box, write the structural formula of the organic compound that would
be formed.
NaBH4
CH3COCH3
HCN
V
PCl5
W
X
ZAFA
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CH.
dil
H2SO4
heat
Y
conc.
H2SO4
170 °C
Br2
Z
[6]
Pg-17
11.
Some reactions involving 2-bromopropane are shown.
CH3CHBrCH3
2-bromopropane
reaction 1
CH3CH(NH2)CH3
reaction 2
X
reaction 3
hydrolysis
reaction 6
HBr
Y
reaction 5
CH3CH2CH2OH
reaction 4
CH3CH2CO2H
(and CH3CH(NH2)CH3
which is removed)
(i) State the reagent needed for reaction 1.
....................................................................................................................................... [1]
(ii) State the reagent needed for reaction 2.
....................................................................................................................................... [1]
(iii) Give the structural formula of X.
[1]
(iv) Name the type of reaction involved in reaction 4 and suggest a suitable reagent.
.............................................................................................................................................
....................................................................................................................................... [2]
(v) State the name of a solid catalyst for reaction 5.
....................................................................................................................................... [1]
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CH.
Pg-18
12. A reaction sequence based on propan-1-ol is shown.
O
CH3CH2C
OH
reaction 1
CH3CH
CH2
reaction 3
CH3CH2CH2
reaction 4
OH
CH3CH2CH2
Br
propan-1-ol
reaction 2
O
CH3CH2C
OH
H
reaction 5
NaCN / H+
CH3CH2C
CN
H
(a) Reactions 1 and 2 can both be carried out using the same reagents.
(i) Identify suitable reagents for reactions 1 and 2.
.............................................................................................................................................
....................................................................................................................................... [1]
(ii) State and explain how the reaction should be carried out to ensure that reaction 2 rather
than reaction 1 occurs.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
....................................................................................................................................... [2]
(b) Identify the necessary reagents and conditions for each of reactions 3 and 4.
reaction 3 ...................................................................................................................................
....................................................................................................................................................
reaction 4 ...................................................................................................................................
....................................................................................................................................................
[2]
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CH.
Pg-19
13. Some reactions of compound P, C H O, are shown.
5
8
compound Q
H2(g)
Ni(s) catalyst
compound R
NaBH4
cold, acidified
KMnO4(aq)
O
compound P
compound S
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CH.
OH–(aq)
I2(aq)
O
compound T +
–
O
(a) (i) Give the structures for organic compounds Q, R, S and T.
Q
R
S
T
[4]
Pg-20
14. 2-hydroxypropanoic acid can be synthesised in four steps from ethanoic acid.
O
step 1
OH
O
step 2
Cl
O
O
step 3
OH
CN
ethanoic
acid
O
step 4
OH
OH
O
2-hydroxypropanoic
acid
(a) (i)
Suggest a reagent for step 2.
....................................................................................................................................... [1]
(ii)
Suggest reagents and conditions for steps 1 and 4.
step 1 ..................................................................................................................................
step 4 ..................................................................................................................................
[2]
ZAFA
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CH.
Pg-21
15.
Some reactions based on 1-bromobutane, CH3(CH2)3Br, are shown.
reaction 1
CH3(CH2)3OH
reaction 5
CH3(CH2)2CHO
CH3(CH2)3Br
reaction 2
reaction 3
ZAFA
CH3(CH2)3C≡N
reaction 6
CH3(CH2)2COOH
CH3CH2CH=CH2
R IQ
BAL
CH.
reaction 4
CH3(CH2)3COOH
(a) For each of the reactions state the reagent(s), the particular conditions required, if any, and the
type of reaction.
For the type of reaction choose from the list.
Each type may be used once, more than once or not at all.
Each reaction may be described by more than one type.
reaction
elimination
hydrolysis
substitution
oxidation
addition
condensation
reagent(s) and conditions
type(s) of reaction
1
2
3
4
5
6
[6]
Pg-21
16.
Some reactions are shown, based on methylpropan-2-ol, (CH3)3COH.
(CH3)3CBr
reaction 1
reaction 2
(CH3)3COH
reaction 3
(CH3)2C=CH2
reaction 4
(CH3)3CBr and (CH3)2CHCH2Br
(a) For each of the reactions state the reagent(s), the particular conditions required, if any, and the
type of reaction.
For the type of reaction choose from the list.
Each type may be used once, more than once or not at all.
Each reaction may be described by one or more than one type.
reaction
hydrolysis
dehydration
substitution
oxidation
addition
condensation
reagent(s) and conditions
type(s) of reaction
1
2
3
4
[5]
ZAFA
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CH.
[3]
Pg-22
17. The structure of glycolic acid is shown.
H
H
O
C
C
OH
OH
glycolic acid
(a) Complete the table to show what you would observe when an aqueous solution of glycolic acid
is added separately to each of the reagents. If a reaction occurs, state the functional group of
glycolic acid that is responsible for the reaction.
reagent
observation with glycolic acid
does a
reaction
occur? /
functional group
Na2CO3(aq)
2,4-DNPH
acidified Cr2O72–
[4]
(b) Two reaction sequences to make glycolic acid are shown.
HCN and NaCN
sequence A
HCHO
sequence B
CH3CO2H
(i)
reaction 1
Br2
reaction 3
X
reaction 2
CH2BrCO2H
CH2(OH)CO2H
reaction 4
CH2(OH)CO2H
Draw the structure of X.
[1]
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CH.
Pg-23
18. The diagram shows a reaction sequence starting from ethanal.
O
H 3C
C
H
OH
HCN and NaCN
H
reaction 1
P
H2SO4(aq)
reaction 2
H3C
C
H
H
reaction 3
C
CO2H
ethanal
C
CO2H
H
Q
R
reaction 4
O
H 3C
C
CO2H
S
(a) (i)
Draw the displayed formula of P.
[1]
(ii)
Name the type of chemical reaction that occurs in reaction 3.
....................................................................................................................................... [1]
(iii)
Write an equation to represent reaction 4.
Use [O] to represent the oxidising agent.
....................................................................................................................................... [1]
(iv)
State the reagents and conditions for reaction 4.
....................................................................................................................................... [1]
ZAFA
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CH.
Pg-24
19. Twopossiblemethodsofmakinglacticacidareshown.
OH
O
C
H3 C
reaction 1
H
H3C
C
H
CN
reaction 2
OH
H 3C
OH
H3C
C
reaction 3
CH2OH
H3 C
C
H
CO2H
O
H
C
lactic acid
reaction 4
CO2H
(ii) Statesuitablereagentsandconditionsforreactions1 and 3.
reaction
reagents and conditions
1
3
[4]
(iii) Namethetypeofreactionthatoccursinreaction2.
.......................................................................................................................................[1]
(iv)
Reaction 4 uses NaBH4.
IdentifytheroleofNaBH4 in this reaction.
.......................................................................................................................................[1]
(v) Lacticacidhasachiralcentre.
Statewhatismeantbythetermchiral centre.
.............................................................................................................................................
.............................................................................................................................................
.......................................................................................................................................[1]
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CH
Pg-25
ORGANIC SYNTHESIS
ALKYL
HYDROGENSULPHATE
KETONE
2y alcohol
ALKENE
ALKANE
ALCOHOL
HALOALKANE
AMINE
ALDEHYDE
NITRILE
AMIDE
CARBOXYLIC ACID
ESTER
1y alcohol
2-HYDROXYNITRILE
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CH.
Pg-26
(e) V is used in a wide range of organic reactions.
Some reactions of V are shown.
W
V
O
reaction 3
O
alkaline
aqueous I2
O–
reaction 4 NaBH4
Y
X
OH
(i)
reaction 5
reaction 6
dehydration
addition
polymerisation
Z
V and W are colourless and soluble in water.
State what you would observe in reaction 3.
....................................................................................................................................... [1]
9701/22/O/N/21
[Turn over
Pg-27
(ii)
Reaction 3 is a redox reaction.
Identify which of the reactants is reduced in this reaction.
....................................................................................................................................... [1]
(iii)
Construct an equation for reaction 4.
Use [H] in the equation to represent an atom of hydrogen from NaBH4.
C6H12O + ..................................................................................................................... [1]
(iv)
X is a mixture of two optical isomers.
Draw the two optical isomers in the boxes provided.
(v)
Both optical isomers of X can be dehydrated to form a single product, Y.
Give the reagent(s) and conditions required for reaction 5.
[2]
....................................................................................................................................... [1]
(vi)
Y can form an addition polymer Z.
Draw one repeat unit of Z.
(vii)
Reaction 6 does not proceed quickly at room temperature.
[1]
Suggest why this is the case.
.............................................................................................................................................
....................................................................................................................................... [1]
[Total: 17]
Pg-28
(c) Citric acid can be made from M in a four-step reaction.
Cl
M
Cl
O
step 1
O
Cl
N
step 2
OH
HO
HO
Cl
Cl
Cl
step 3
citric acid
O
O
HO
N
OH
O
O
step 4
OH
OH
OH
HO
N
Complete the table for each step of the reaction sequence to identify:
● the reagents and conditions required
● the type of reaction.
step
reagent and conditions
type of reaction
1
2
dilute sulfuric acid
3
4
dilute sulfuric acid
[5]
[Total: 12]
© UCLES 2021
9701/23/M/J/21
[Turn over
Pg-29
4
Some reactions of compound G are shown.
G
O
OH
H
reaction 1
HOOC(CH2)2COOH
reaction 2
O
reaction 3
Tollens’ reagent
H2SO4, heat
under reflux
reaction 4
Na
H
O
(a) (i)
OH
HO
O
State the type of reaction that occurs in reaction 1.
....................................................................................................................................... [1]
(ii)
Suggest the reagent(s) and conditions required for reaction 1.
.............................................................................................................................................
....................................................................................................................................... [2]
(iii)
Draw the structure of the organic product, H, from reaction 2.
[1]
(iv)
State what you would observe in reaction 3.
....................................................................................................................................... [1]
(v)
Give the type of reaction shown by reaction 4.
....................................................................................................................................... [1]
© UCLES 2020
9701/22/O/N/20
[Turn over
Pg-30
5
The reaction sequence shows how ethene, C2H4, can be converted into other organic molecules.
C 2H 4
reaction 1
OH
reaction 5
reaction 2
Cl
reaction 6
NH2
O
reaction 3
HO
N
reaction 4
heat with dilute acid
W
(a) Complete the table to give
● the name of the reaction mechanisms of reactions 1 and 6
● the reagents and conditions required for reactions 1, 2 and 6.
reaction
name of reagents
and conditions
name of
mechanism
1
2
6
[6]
© UCLES 2020
9701/22/M/J/20
Pg-31
(b) In reaction 3 the organic molecule reacts with HCN and a KCN catalyst.
(i)
Complete the diagram to show the mechanism of the reaction occurring.
Include all relevant dipoles, lone pairs and curly arrows in your answer.
H
H
C
H 3C
O
C–
N
H3C
C
CN
H
–
O
H
H 3C
C
OH
CN
C
C–
N
N
[3]
(ii)
Name the functional groups present in the product of reaction 3.
....................................................................................................................................... [2]
(c) Draw the structure of the organic molecule W formed in reaction 4.
[1]
[Total: 12]
Pg-32
(b) F is an organic molecule which has the molecular formula C3H6O2.
When F is heated with NaOH(aq) followed by H2SO4(aq) the products G and H are made.
F
NaOH(aq) followed
C3H6O2
by H2SO4(aq)
G
+
H
Separate samples of G and H are added to
Na2CO3(aq)
sodium metal
alkaline aqueous iodine.
●
●
●
The observations are described in the table.
reagent(s)
G
H
Na2CO3(aq)
colourless bubbles of gas produced
no visible reaction
Na(s)
colourless bubbles of gas produced
colourless bubbles of gas produced
alkaline aqueous iodine
no visible reaction
yellow precipitate forms
(i)
Complete the table to identify the functional groups present in F, G and H.
functional group
F
G
H
[3]
(ii)
Name the yellow precipitate formed when alkaline aqueous iodine reacts with H.
....................................................................................................................................... [1]
(iii)
Draw the structures of G and H.
G
H
[2]
[Total: 11]
© UCLES 2020
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Pg-33
+
By the ______________________________of ester
H3O /Heat
By the _______________________of alkane nitrile
+
H3O /Heat
By the _____________________of alkanoyl halide
By the _____________________of alkanamide
H2O
+
H3O /Heat
_________
By the _____________of primary alcohol
K2Cr2O7 / H+
By the _____________of aldehyde
Metal Carbonate
Metal Bicarbonate
Metal hydroxide
_________
Metal oxide
oxidation only methanoic & Ethanedioic acid
Metal
_________
Carboxylic acid
K2Cr2O7 / H+
LiAlH4 in dry ether
Combustion
alcohol
+
H3O /Heat
PX 3 , PX5 , SOX 2