Answers to Sem 3 Exercise (Essay Part)

1. (a) (i) Structural isomers are compounds which have similar molecular formula
but different structural formula
(ii) Geometrical isomers are different compounds having the same molecular
formula and structural formula, but the spatial arrangement of atoms or
group are different due to presence of double bonds in the molecule that
prevent rotation
(b) Element C H
% by mass 85.7 14.3
No. of mole 7.14 14.3
Ratio 1 2
Empirical formula of X = CH2

Using pV = nRT
1 x 56/1000 = 0.14/W x 0.082 x 273
W = 56
(CH2)n = 56
n=4
Molecular formula of X = C4H8

(i) A is but-2-ene

(ii) B is but-1-ene

Y is propanal, CH3CH2CHO
Y reacts with 2,4-dinitrophenylhydrazine, so Y can be either ketone or
aldehyde
But Y reacts with Fehling’s solution to form brick red precipitate, thus Y is
an aldehyde
(iii) C is 3-methylpropene

Dehydration of 2-methylpropan-2-ol
2. (a) Bromoethane is heated with alcoholic potassium cyanide
CH3CH2Br + KCN  CH3CH2CN + KBr
Propanonitrile is then warmed with dilute sulphuric acid
CH3CH2CN + 2H2O  CH3CH2COOH + NH3

(b) B is butan-2-ol
Alcohol reacts with phosphorus pentachloride to liberate HCl
CH3CH2CHOHCH3 + PCl5  CH3CH2CHClCH3 + HCl
Butan-2-ol has one chiral carbon, so it is optically active

(c) (i) Cl2 + AlCl3  δ+Cl ------ δ-Cl ------ AlCl3

(ii) The lone pair electrons of oxygen in the ─OH group delocalise into the
benzene
This enhances the electron density of the benzene ring and hence
activates it towards electrophilic attack
Therefore, for the chlorination of phenol,
1. a lesser stringent condition is used (a catalyst such as AlCl3 is not
required)
2. polysubstitution takes place whereby the 2,4,6-positions are substituted

(d) Trichlorophenol is a stronger acid than phenol

The 3 electronegative chlorine atoms help to disperse the charge on
trichlorophenol by inductive effect, This stabilises and increases the tendency
of trichlorophenol to dissociate to form H+

3. (a) 2-phenylmethylbutan-2-ol is a tertiary alcohol. Hence, a Grignard reagent and

a ketone are required for the reaction
(i) Any two of these pairs
 (ii)

(b) (i)

(ii) Compound ─CH2Cl is produced. Compounds II, III and IV do not

react with AgNO3.

Conditions: Pass chlorine into methylbenzene boiling under reflux and in
the presence of sunlight
(iii)

(iv) ─CH2Cl is insoluble in water, but soluble in ethanol. So ethanolic

silver nitrate is used to enable it to dissolve in the reaction mixture.

4. (a) (i) Element C Cl H

% by mass 66.4 28.1 5.5
Mole ratio 5.5 0.79 5.5
Simplest ratio 7 1 7
Empirical formula of P = C7H7Cl
[7(12) + 7(1) + 35.5]n = 126.5
n=1
Molecular formula of P = C7H7Cl
(ii) P is an aromatic compound (ratio C:H is 1:1)
Cl atom is on side chain since it can be hydrolysed
P:

Hydrolysis of P produces phenyl methanol, Q

 Controlled oxidation of Q produces benzaldehyde, R

Benzaldehyde, R reacts with 2,4-dinitrohydrazine to form a hydrazone, S.

Further oxidation of benzaldehyde, R produces benzoic acid, T

(b) (i) Nucleophilic substitution

CH3 CH3
│ │
CH3 ─ C ─ CH3 + KOH CH3 ─ C ─ CH3 + KBr
│ │
Br OH

Mechanism:
CH3 CH3
│ │
CH3 ─ C ─ CH3 CH3─C─CH3 + Br-
│ ○
+

Br
Combination of the carbonium ion with OH- from KOH
CH3 CH3
│ │
CH3─C─CH3 + OH -
CH3─C─CH3
○
+ │
OH
(ii) The rate equation is rate = k[2-bromo-2-methylpropane]
Is independent of conc [OH] or [KOH]
Hence, conc. of KOH has no effect on rate

5. No answer given

6. No answer given
7. (a) (i)

Bimolecular nucleophilic substitution

(ii) Rate increases
Atomic size of Br > Cl
Hence, the C─Br bond is weaker and is easier to break than C─Cl bond

(iii) reflux
CH3CH2CH2Cl + NaOH(aq) CH3CH2CH2OH + NaCl
conc. H2SO4
CH3CH2CH2OH CH3CH=CH2
o
180 C
CH3CH=CH2 + HCl  CH3CHClCH3
(b) (i)

(ii) Serylalanine or alanylserine

(iii)

8. They don’t react with Fehling’s solution – they are ketones

A and B give positive iodoform test – they have the structure CH3C=O or
methylketone
Boiling point of A > B – A is less branched compared to B
A is CH3COCH2CH2CH3
B is CH3COCH(CH3)2
C is CH3CH2COCH2CH3
D and E give a positive test with Fehling solution – they are aldehydes
D is optically active. Hence isomers of D are

Reduction of E gives a long chain compound, F

E is CH3CH2CH2CH2CHO
 F is CH3CH2CH2CH2CH2OH
P is copper(I) oxide

9. (a) In G, the Cl atom is bonded to the side chain hence it can be replaced by
hydroxide during hydrolysis.
G is

In J, the Cl atom is attached to the aromatic ring. The C-Cl bond in H is less
polar and strong.
J is

(b)
 (c) N has a chiral centre because it exists as a pair of enantiomers
It is an alcohol as it reacts with PCl5 to give HCl gas.
N is CH3CH(OH)CH2CH3

10. (a) HCl or H2SO4 (accept H+ or acid)

Conc(if HCl only) / dilute / aqueous + heat
(b) Two rings only (1 ring around the α-C of tyrosine and around the α-C of
lysine)
(c) +NH3CH2COO-
(d) (i) NH2CH2CO2-
(ii) (Na+)─O─C6H4─CH2CH(NH2)CO2-
(iii) (Cl-)+NH3(CH2)4CH(NH3+)CO2H(Cl-)
(iv) HO─C6H2Br2─CH2CH(NH2)CO2H
(e)

(f)

(iii) Condensation polymerisation

11. No answer given

12. No answer given

13. No answe given

14. No answer given

15. (a) (i) 4-methylphenol dissolves in NaOH(aq) to form a soluble salt

Phenylmethanol does not dissolve in NaOH

(ii) 4-methylphenol decolourises bromine and forms a white precipitate

Phenylmethanol – colour of bromine remains unchanged and there is no

white precipitate
(b) (i)

(ii)

(iii) Both R and S are heated with Tollen reagent / Fehling’s reagent
S – metallic silver (silver mirror) is formed / brick red precipitate of Cu2O is
obtained
R – no silver mirror formed / no brick red precipitate
(iv) P: Q:

(v) CH3C(Cl2)CH3 + 2KOH  CH3COCH3 + 2KCl + H2O

CH3CH2CHCl2 + 2KOH  CH3CH2CHO + 2KCl + H2O

16. (a) (i) B contains a chiral carbon because optically active

A fumes in moist air, thus A has acyl functional group / -COCl
B: A:

Reaction of A with NaOH produces. On acidification, C is obtained.

 (ii) H CH3
│ │
Cl ─ C ─ COCl + CH3 ─ CH ─ CH3  Cl─CH─COOCH─CH3 + HCl
│ │ │
CH3 OH CH3
(b) (i) Geometrical isomerism for L
cis-isomer:

trans-isomer:

(ii) Reaction of L with an aqueous solution of hot sodium hydroxide

CH3(CH2)3CH2OH

(c) Compound: 1-pentanol

Conditions: conc. sulphuric acid, reflux/ heat

17. (a) (i) order: W, Y, X

W, Y, X act as Lewis bases
X is the strongest base because ethyl group is an electron donor by
inductive effect
Y is more basic than W because the lone pair electron on the N atom is
not delocalised
W is less basic than Y because the lone pair electron on the N atom is
delocalised into the benzene ring
(ii) pKb value > 9.39
Z is a weaker base than W
Presence of Cl, an electron withdrawing group reduces the donating
potential of the lone pair electron on the N atom through inductive effect
(b) Conc. H2SO4 and HNO3 , 55oC
18. (a) (i) Terylene / Dacron

(ii) Condensation polymerisation

To make cloth / sleeping bags etc
(b) (i) K: functional group is –OH
Isomers: CH3CH2CH2OH and CH3CHCH3OH
Warm isomers separately with alkaline iodine,
CH3CHCH3OH gives a yellow precipitate while CH3CH2CH2OH does not
CH3CHCH3OH + 4I2 + 6OH-  CHI3 + 5I- + 5H2O + CH3COO-
(ii) L: functional group is –C=O
Isomers: CH3CH2CHO and CH3COCH3
Warm isomers separately with Tollen reagent
CH3CH2CHO gives a silver mirror but CH3COCH3 does not.
CH3CH2CHO + 2[Ag(NH3)2]2+ + OH-  CH3CH2COO- + 2Ag + 2NH4+ +
2NH3

19. (a) W is 2-chloropropan-1-ol

X:

Y:

Z:

H
│
CH3─C─COO- + 4I2 + 6OH-  CHI3 + -OOC─COO- + 5I- + 5H2O
│
OH

OOC─COO- + 2H+  COOH

-

│
COOH
 (b) (i)

(ii)

The liquid mixture of composition C1 boils at T1. The vapour given off
ascends the column and condenses into liquid with composition C2.
Liquid at composition C2 boils at T2. The vapour given off ascends the
column and condenses into liquid with composition C3.
The process repeats and the mole fraction (%) of benzene increases
going up the column. Eventually, pure benzene distilled over as the
first distillate
As more and more benzene distills over, the liquid remaining in the
flask gets richer in ethylbenzene
Eventually, only pure ethylbenzene left over in it and will be distilled
over at its boiling point.

20. (a) (i) Add a few drops of water into each sample
Only ethanoyl chloride produces white fumes.
CH3COCl + H2O  CH3COOH + HCl
(ii) Add Na2CO3 (NaHCO3) to sample and deliver gas produced into
limewater

Only has effervescence and gas produced turns limewater

chalky.

2 + Na2CO3  2 + H2O + CO2

(b) (i)
 (ii)

(iii)

21. (a)
NaOH(aq) MnO4-/H+
C4H9Br (P) C4H10O (Q) C4H8O (R)
decolourises MnO4-/H+ orange precipitate with
2,4-dinitrophenylhydrazine

R gives orange precipitate with 2,4-dinitrophenylhydrazine

R contains carbonyl group, ─C=O  aldehyde or ketone
Both Q and R react with alkaline iodine to form a yellow precipitate
H
│
Q – alcohol contains ─C─CH3,
│
OH
H H
│ │
Q: CH3CH2─C─CH3 P: CH3CH2─C─CH3
│ │
OH Br
Q is oxidised to R – ketone, contains –C=O-CH3
O
││
R: CH3─CH2─C─CH3

T reacts with PCl5 to liberate white fumes, T has –OH group

 T (C8H18O) is a tertiary alcohol.
(b) (i) Phenol is a weak acid, reacts with aqueous sodium hydroxide to produce
a water soluble ionic salt

Phenol does not react with aqueous sodium carbonate because phenol is
a weaker acid than cabronic acid.
(ii) Methanoic acid / formic acid, HCOOH contains aldehyde group, is
oxidised to carboxylic acid.

(iii) Styrene undergoes addition polymerisation, forms a transparent solid

when exposed to air.

22. (a) (i) Relative molecular mass (C7H6)n = 180

(12x7+6)n = 180  90n = 180  n = 2
The molecular formula = C14H12
(ii) W:

cis-trans isomers of W:
 Structure of X:

+ 2HBr 

(b) When aldehydes react with a solution of 2,4-dinitrohydrazine, a small

molecule of H2O is eliminated.

H2O, C2H5OH
(i) Br(CH2)4Br + 2KCN N≡C(CH2)4C≡N + 2KBr
Reflux
N≡C(CH2)4C≡N + 4[H]  H2N(CH2)6NH2
Reducing agents
1. Na / C2H5OH at room temperature
2. H2(g) / Ni at 180oC
3. LiAlH4 / dry ether, followed by H3O+ at room temperature
(ii)
23. (a) CH3─CH=CH─CH3
CH3─CH─CH2─CH3
│
Cl
(b) A: CH3CH2Cl D: CH2Br─CH2Br
B: CH3CH2OH E: CH2OH─CH2OH
C: CH2=CH2
(c) Ethanolic KOH
(d) Monomer of polyester
(e) Heat with ethanolic silver nitrate
1-iodohexane: yellow precipitate of AgI
1-chlorohexane: white precipitate of AgCl
Heat with ethanolic silver nitrate
Chlorocyclohexane: white precipitate
Chlorobenzene: no precipitate
Add acidified KMnO4
1-chloro-1-butane: decolourisation of KMnO4
1-chlorobutane: KMnO4 does not decolourise

24. (a) Tetrahydroisoquinoline is the stronger base. In tetrahydroisoquinoline, the

unshared electron pair is delocalised into the aromatic ring, making it less
available to accept proton, whereas tetrahydroisoquinoline resembles an
alkylamine
(b) 3,4-difluorophenylamine is a weaker base than phenylamine because the two
F atoms are electron-withdrawing and they reduce the availability of the lone
pair of electrons on the N atom to accept a proton
(c) An ethyl group, CH3CH2 is transferred from triethylaluminium to titanium(IV)
chloride to produce a complex

Ethene molecules act as Lewis bases and are bonded to titanium which has
vacant d orbitals. These ethene monomers are inserted between the titanium
and the ethyl group to form a polymer.

The process is terminated when a hydrogen atom is added to a titanium

atom, and the poly(ethene) chain is separated from titanium.
(d) The poly(ethene) polymer formed by the addition polymerisation process
using the Ziegler-Natta catalyst is a linear polymer and of high density and
high melting point.
(e) Proteins and polypeptides
Nylon has peptide linkages, CONH, which are also found in proteins and
polypeptides
25. No answer given

26. (a) CH3COOH, HCOOH, ClCH2COOH

RCOOH(aq) + H2O(l) ↔ RCOO-(aq) + H3O+(aq)
Acid conjugate base
─CH3 is electron releasing group and Cl is electron withdrawing group
─CH3 of ethanoic acid causes O─H bond of the COOH group to be less
polarised, thus less able to ionise // ─CH3 of ethanoic acid destabilises the
CH3COO- conjugate base and shifting the equilibrium position to the left.
Cl of chloroethanoic acid causes O─H bond of the COOH group to be more
polarised, thus more able to ionise // ─Cl of ethanoic acid stabilises the
CH3COO- conjugate base and shifting the equilibrium position to the right.
(b) (i) reagent and condition: acidified KMnO4 solution, room temperature
Cyclohexene decolourises the purple colour of acidified KMnO4 while no
obvious observation for cyclohexane

(ii) reagent & condition: acidified KMnO4, heat

Toluene decolourises the purple colour of KMnO4 while no obvious
observation for benzene

(c) Free radical substitution

Cl2  2Cl•
CH3CH2CH3 + Cl•  (CH3)2CH• + HCl
(CH3)2CH• + Cl2  (CH3)2CHCl + Cl•

27. (a) (i) Phenol

Amide
(ii) Alkaline hydrolysis

CH3COONa
(b)

(c) H2N─*CH─COOH H2N─*CH─COOH

│ │
CH2 CH2
│ │
OH COOH
Has a chiral carbon
Shown as * in the structure
Mirror images are not superimposed
Rotate plane polarised light
28. (a) (i) RMM of Y = 74
(ii) m/e Fragment ions
29 C2H5+
45 COOH+
57 CH3CH2CO+
74 CH3CH2COOH+
(iii) Liquid X has a fruity smell: ester
X is hydrolysed in acid condition to form one alcohol and one carboxylic
acid
Y is

Z is methylalcohol or

because Z gives a positive iodoform test

Empirical formula of Z = C3H8O

(C3H8O)n = 60
n=1
Molecular formula of Z = C3H8O
Z is propan-2-ol, or

X is

(b) Aqueous sodium hydroxide is added to both compounds at room temperature

Phenol dissolves in sodium hydroxide to form colourless solution
Cyclohexanol does not dissolve in NaOH
C6H5OH + NaOH  C6H5ONa + H2O
29. (a) (i) A fixed amount of citric acid is added to an excess aqueous solution of
sodium carbonate
The volume of carbon dioxide evolved is measured
2C6H8O7 + 3Na2CO3  2C6H5O7Na3 + 3CO2 + 3H2O
If 0.01 mole citric acid is used, the volume of CO2 evolved should be:
0.01 x 3/2 x 24 dm3 = 360cm3 at room temp and pressure
OR
A fixed amount of citric acid is titrated with aqueous solution of sodium
hydroxide.
The volume of sodium hydroxide is measured
C6H8O7 + 3NaOH  C6H5O7Na3 + 3H2O
Or MaVa/MbVb = 1/3
If 10.0cm3 of 0.01 mol dm-3 citric acid is used,
The volume of 0.01 mol dm-3 NaOH titrated should be:
0.01x10.0x3 / 0.01 = 30.0cm3

(ii) with ethanoyl chloride

With thionyl chloride

With aqueous potassium hydroxide

(b) (i)

(ii) Monomers with C=C are joined together by covalent bonds to form large
molecule.
(iii)
 (iv) The properties of natural rubber can be improved by vulcanization / raw
rubber is heated with 8% of sulphur
Vulcanized rubber is more elastic because it can easily return to its
original shape and length after the stretching force is removed
The polymer chains do not easily slip over each other because they are
held by sulphur bridges.
Vulcanized rubber has a higher melting point than unvulcanized rubber or
more heat resistant
When sulphur is added, the relative molecular mass of the polymer is
increased, causing the van der Waals attractive forces between the
chains to increase
Vulcanized rubber is not easily oxidised compared to unvulcanized rubber
Because the formation of sulphur bridges reduces the number of double
bonds in the polymer

30. (a) (i)

Catalyst: phosphoric acid

(ii) Oxidation

Decomposition of hydroperoxide with dilute sulfuric acid

(b) (i) ─OH in phenol is a ring activating group / lone pair electrons on oxygen
atom in –OH group can be delocalized into the benzene ring
Phenol more easily attacked by an electrophile (or NO2+) compare to
benzene
Equation to form nitrobenzene
Equation to form 2-nitrophenol and 4-nitrophenol
(ii) Elimination reaction / dehydration
To form but-1-ene and 2-butene
Any one equation to form 1-butene or 2-butene
2-butene exists as pair of cis-trans isomers / shows geometrical
isomerism
Draw structures of the cis and trans isomers and label them

31. (a) Describe test using either one of the following reagents:
Tollen reagent / Fehling’s solution / iron(III) chloride
Observation
Equation
 (b) Step 1: reagent – hydrogen cyanide, HCN
Step 2: reagent – LiAlH4 in ether solvent / NaBH4 / Na in ethanol

(c) (i)

(ii)

(d) (i)

(ii)

32. (a) (i) Phenylamine < ammonia < ethylamine

(ii) The strength of a base depends on its ability to donate its lone pair
electrons for sharing with a proton
In phenylamine, the lone pair electron on N atom is delocalised into the
ring
The p orbital of N atom overlaps with those of the carbon atoms in the
ring. Thus it is not readily shared with protons
In ethylamine, the ethyl group has an electron donating effect.
This makes the lone pair electron on N atom more available for sharing
with protons
(b) (i) Add acidified KMnO4 to methylbenzene and heat.
Benzoic acid is formed
C6H5CH3 + 3[O]  C6H5COOH + H2O
Add PCl5 and heat, benzoyl chloride is formed.
C6H5COOH + PCl5  C6H5COCl + POCl3
Add conc. ammonia: C6H5COCl + NH3  C6H5CONH2 + HCl
 (ii) Chlorine gas, sunlight and boiling methylbenzene
Chloromethylbenzene is formed
C6H5CH3 + Cl2  C6H5CH2Cl + HCl
Add aqueous NaOH and reflux
C6H5CH2Cl + NaOH  C6H5CH2OH + NaCl
To prove the presence of –OH group in (ii), add PCl5
White fumes of HCl is observed
C6H5CH2OH + PCl5  C6H5CH2Cl + HCl + POCl3

33. (a) X is an ester (sweet smelling liquid)

Y is phenol (formation of white precipitate with bromine water)
Reduction of X would produce two alcohols. Y is a tertiary alcohol, Z is a
primary alcohol

Hydrolysis of X:

Reaction of Y with bromine water:

Reduction of X:

Dehydration of Z:
(CH3)2CHCH2OH  (CH3)2C=CH2 + H2O

(b) (i) Ethyl magnesium bromide can be prepared by heating bromoethane with
magnesium at 35oC in dry ether
(ii) CH3CH2MgBr + CH3COCH3  CH3CH2C(CH3)2 + MgBr+
│
O-
CH3CH2C(CH3)2 + MgBr+ + H2O  CH3CH2C(CH3)2 + Mg(OH)Br
│
O-
34. (a) Optical isomerism occurs in compounds with the same structural formula but
differ in their effect on plane polarised light
Optical isomers contain a chiral carbon
Are non-superimposable or mirror images to one another
Rotate the plane of plane-polarised light in opposite direction but to the same
degree
Example:

(b) Since X gives white fumes with PCl5, X is an alcohol.

X gives a yellow precipitate with alkaline iodine shows that X has the structure
CH3CH(OH)R
Hence, X is 1-phenylethanol, CH3CH(OH)C6H5
Equations: CH3CH(OH)C6H5 + PCl5  CH3CH(Cl)C6H5 + HCl + POCl3
X
CH3CH(OH)C6H5 + 4I2 + 6NaOH  CHI3 + C6H5COONa +
5NaI + 5H2O
excess H2SO4
CH3CH(OH)C6H5 CH2=CH(C6H5) + H2O
X Y
X undergoes dehydration to form phenylethene, CH2=CH(C6H5)

(c) A and B are aromatic compounds, highly unsaturated.

A is phenol
OH
│
B contains –OH and the structure CH3─C─
│
H
4-ethylaniline reacts with nitrous acid to produce A
Bromobenzene reacts with Mg/dry ether to produce a Grignard reagent. The
Grignard reagent then reacts with ethanal to produce a secondary alcohol, B.
A: B:

35. (a) (i)

(ii) Reagent: sodium hydroxide

Condition: reflux
Observations: R – no visible reaction
S – gas with a characteristic smell, NH3 is given off
 (b) Step I – KCN / ethanol, reflux
Step II – HCl, reflux
Step III – PCl5 or SOCl2
A: CH3CH2CH2CN
B:

(c)

Step 1 – oxidation of methylbenzene

Reagent – KmnO4 and H2SO4
Condition – reflux
Step 2 – esterification
Reagent – ethanol and conc. H2SO4
Condition – reflux

36. (a) (i) Elimination reaction

(ii) ClCH2CH2CH2CH2Cl  CH2=CH─CH=CH2 + 2HCl
(iii) Addition polymerization

(b) (i) Toluene undergoes electrophilic substitution reaction (to form ortho and
para chlorotoluene)
 (ii) Name of mechanism: electrophilic addition

(c) B is more acidic than A

R-OH + H2O  R-O- + H3O+
NO2 is electron withdrawing, stabilises phenoxide ion, equilibrium shifts more
to the right
CH3 is electron donating, destabilises phenoxide ion, thus equilibrium shifts
more to the left

37. (a) Y
Because molecules of Y form intermolecular hydrogen bonds whereas the
intermolecular forces between molecules of X are the weak Van der Waals
forces
(b) (i) Step 1
Reagent: chloromethane in the presence of anhydrous aluminium chloride
Equation:

Step 2
Reagent: conc. H2SO4 and HNO3
Condition: 55oC
Equation:

(ii) Step 1
Reagent: add tin, conc. HCl followed by aqueous NaOH
Equation:

Step 2
Reagent: acidified KMnO4 solution and reflux
Equation:

(iii) Y dissolves in hydrochloric acid while X does not.

(c) Y
38. (a) (i) The benzene ring has electron withdrawing effect, this makes the O-H
group bond quite polar to donate proton. With NaOH(aq), phenol forms a
stable salt of sodium phenoxide.
On the other hand, 1-butanol is neutral. The butyl group is rather non-
polar and this orevents its reaction with NaOH(aq).

(ii) Methanoic acid contains aldehyde group in its structure. Hence just like
aldehydes it can be oxidised by acidified KMnO4 to carbonic acid which
decomposes to carbon dioxide and water.

(iii) Methylamine is a base solution and will react with dilute HCl to produce a
water soluble ionic salt.
CH3NH2 + HCl  CH3NH3Cl

(b)

39. No answer given

40. No answer given

41. (a) (i) CxHy + (x+y/4)O2  xCO2 + y/2H2O
Anhydrous CaCl2 absorbs water and KOH absorbs carbon dioxide – the
mass of water is 0.72g and the mass of carbon dioxide is 1.76g

Mass of C = (12.0 x 1.76)/44.0

= 0.48g
Mass of H = (2.0 x 0.72)/18.0
= 0.08g

Element C H
Mass/g 0.48 0.08
No. of moles 0.48/12 = 0.04 0.08/1 = 0.08
Mole ratio 1 2
Empirical formula is CH2.
(ii) The mass of hydrocarbon = mass of C + mass of H
= 0.48 + 0.08
= 0.56g
Relative molecular mass = 0.56/0.01
= 56
(CH2)n = 56
n[12+2(1)] = 56
n=4
Molecular formula is C4H8
(b) (i)
─NH2

(ii) (CH3)2C(OH)2
(CH3)2C=O
(iii)
─CH(OH)CH2CH3

(c)
42. (a) (i)

(ii) C=C
(iii) Harder, more elastic, less sticky
(iv) Hard and brittle
(v) Sulphur

(vi) Elastomers are polymers that stretch when pulled and return to their
length and shape when the force is released
(b) (i) rate = k[C3H7-C(Br)(CH3)-C2H5]
(ii) Constant
Because OH- ion does not involve in the rate of determining step
(iii) Nucleophilic substitution
(iv) Optical isomers

43. (a)
 (b) (i) SnCl2 is a weak reducing agent, but LiAlH4 is a very strong reducing
agent which can reduce –COOH group to –CH2OH.
(ii) SnCl4  SnCl2 + Cl2
Sn undergoes reduction, while Cl undergoes oxidation, the reaction is a
redox reaction.
(iii)

White fumes and a white solid are observed

Due to hydrolysis reaction / SnCl4 + H2O  SnO2 + 4HCl
(c) Sodium nitrite and dilute HCl are added to the mixture
Effervescence of a colourless gas is observed

OR
A little aqueous copper(II) sulphate is added to the mixture.
A dark blue solution is observed

(d) (i) Ethanol, conc. sulphuric acid, reflux

(ii)

44. (a)

2-bromo-2-methylpropane is major product as its formation involved stable

tertiary free radical (CH3)3C•
(b) (i)

Both X and Y, each has a chiral carbon atom bonded to 4 different groups
making them optically active.
X is an alkene with one double bond as only 1 mole of H2 can be added.
(ii) X is unsaturated hydrocarbon but Y is saturated
Bromine water / acidified KMnO4 is added to liquids X and Y in separate
test tubes
X decolourises reddish brown bromine water / purple colour of KMnO4
CH3CH=CHCH(CH3)CH2CH3 + Br2  CH3CH(Br)CH(CH3)CH2CH3 /
CH3CH=CHCH(CH3)CH2CH3  CH3CH(OH)CH(OH)CH(CH3)CH2CH3

(c)