H H H H H H
(b) (i) R
HadicalC substitution
C C C C C Br (d) (i) 2
,2-dimethylpentane
(ii) H H H H H H (ii)
H C C C C C C Br
H H H H H H
2-methylhexane 2,3-dimethylpentane
H C C C C C C Br
H H H H H H
H H H H H H
H H H H H H
H H H H H H
H C C C C C C H
2,2,3-trimethylbutane 2,4-dimethylpentane
H H H H H H
H C C C C C C H
H H H H Br H
H C C C C C C H
H H H H Br H
H H H H H H
H H H H Br H
compound C
H H H H H H
H C C C C C C H
H H H H H H
H C C C C C C H
H H H Br H H
(c) H
H C C C C H C H C H
H H H H Br H H
C CH H HC2H5 Br C H C H C2H5
+
C2H5 C2H5
Br
Br +
–
Br
(iii) 2
,2,3-trimethylbutane
Br –
Intermediate (iv) B ranched chained isomers are more difficult to
(d) (i) C2H5 H C2H5 C2H5 pack together. The more branching the less van
der Waals forces present and the higher the
C C C C boiling point.
(e) (i) A fuel whose feedstock is obtained from plants or
H C2H5 H H
animal waste.
trans cis (ii) F ossil fuels are non-renewable because they take
In the trans isomer the C2H5 groups are arranged millions of years to be formed.
diagonally across the double bond. Ethanol is renewable as sugar can be grown.
(ii) T he product does not have a double bond and so 3 (a) (i) U V radiation
the groups can freely rotate to give the same (ii) initiation Cl2 → 2Cl·
structure. propagation C4H10 + Cl? → C4H9? + HCl
2 (a) T
he separation of the components in a mixture of C4H9? + Cl2 → C4H9Cl + Cl·
liquids on the basis of their boiling points. (iii) C l? + C4H9? → C4H9Cl
(b) C 7H16 → C4H10 + C3H6 (iv) H omolytic
(c) (i) H (b) (i) 2 ,3-dichlorobutane
(ii) Cl (iii) Cl
H C H
H H H
C
H C C H Cl Cl
4 (a) (i) A
compound containing carbon and hydrogen only
H C C H
C (ii) C 10H22
H H (iii) C 5H11
H H
7H16 → C7H14 + H2
(ii) C (b) (i) A species with an unpaired electron
(ii) U V radiation
(iii) H omolytic
(iv) C l? + C12H26 → C12H25? + HCl
C12H25? + Cl2 → C12H25Cl + Cl?
+ H2
C C H C C H H C
Step 1 + Step 2
H H
5 Margarine is made from the hydrogenation of unsaturated H O
H+ +
vegetable fat. It is carried out using hydrogen in the –
O H
presence of a nickel catalyst.
+ +
Poly(propene) can be made from propene H by
H H H
H H
polymerisation. This process requires high temperature CH3 H CH3 H CH3 H
CH3 H
andn pressure
C and
C often uses a catalyst.C C
H H C H C H H C C H H C C H H C C H +
H CH3 Step 1 + Step 2 Step 3
H CH3 n
n C C H C CH H O H O H
H+ +
–
H CH3 H H H
H CH3 n O
CHH3 H + CH3 H CH3 H
HH H H +
CH3 H H
C of
Structure C C Step 1 C HC CC C TwoHrepeat units H C C H H C C H + H+
+ Step 2 Step 3
polymer H H H H
H H
H CH3 CH3 H H O H O H
+
Structure of H+ C C– C C
Two repeat units
Addition
polymer polymers are non-biodegradableO
and do not H H H
break down naturally in the environment. If burned they (ii) H
+ acts as a catalyst because it is not consumed
H CH3 H + CH3 +
produce toxic fumes. H H in the reaction
In future these polymers may be recycled or incinerated (d) C H3CH(OH)CH3 + 4½O2 → 3CO2 + 4H2O
for energy production. They may be cracked to produce (e) CH3COOH Ethanoic acid
more useful organic materials. 4.44
o of moles = _____
2 (a) (i) N
= 0.0600 mol
6 (a) (i) u
nsaturated contains double or multiple bonds 74. 0
hydrocarbon contains carbon and hydrogen only 5.48
(ii) N o of moles = _____ = 0.0400 mol
(ii) a ngle a 109.5° 137
angle b 120° Actual moles
_______________ 0.0400
(iii) % = × 100 = _______
× 100
(iii) H H H H Expected moles 0.0600
= 66.7%
C C C C (b) (i) H Cl H Cl H Cl
H H H H
C C C C C C
Adjacent p-orbitals overlap sideways to form a
π-bond. H H H H H H
(ii) H armful toxic fumes are produced
(iii) R
ecycling of polymers / using as a feedstock
Cracking polymers / as a source of fuel
Development of biodegradable alternatives
C C C O H C C C
H H OH H
H H H Isomer 1
H
(ii) C =C double bond or alkene H
(b) (i) K 2Cr2O7/H+ (acidified dichromate)
H C H
(ii) C H2CHCH2OH + [O] → CH2CHCHO + H2O H CH3 H H H
(c) A crylic acid because the presence of a strong sharp
absorbance at 1650 cm−1 to 1720 cm−1 indicates a H C C C OH H C C C H
C=O. The presence of a strong broad absorbance at
2500 cm−1 to 3300 cm−1 indicates the presence of an H H H H OH H
O–H in a carboxylic acid.
(d) (i) CH2=CHCOOH + CH2=CHCH2OH → Isomer 2 Isomer 3
CH2=CHCOOCH2CH=CH2 + H2O
(b) (i) C
olour changes from orange to green
(ii) H H O
(ii) C 4H9OH + 2[O] → C3H7COOH + H2O
(iii) isomer 2
C C C O CH2 CH CH2
56
H2 12 + 2 = 14 ___ = 4
(c) (i) C
H 14
4 (a) A
test tube of the halogenalkane is placed in a water ∴ C4H8
bath at 60 °C. A solution of AgNO3 and ethanol (ii) C 4H9OH → C4H8 + H2O
(which acts as a common solvent) is placed in the (iii) isomer 1
water bath. The two solutions are then added (d) (i) H
2SO4
6.96
together and the time taken to form the precipitate is (ii) N o of moles = _____ = 0.0600
found. 116
Actual
_________ 0.0600
The fastest will be the iodoalkane and the slowest will (iii) % = × 100 = _______
× 100
Expected 0.100
be the chloroalkane.
= 60.0%
Iodoalkanes undergo hydrolysis faster than
bromoalkanes which in turn hydrolyse faster than 2.3 Energy
chloroalkanes. 1 (a) (i) T
he enthalpy charge when one mole of
This is because the carbon–halogen bond gets substance in its standard state is formed from its
stronger from an iodoalkane to a bromoalkane with elements in their standard states
the chloroalkane having the strongest carbon–halogen (ii) 6 C(s) + 7H2(g) → C6H14(l)
bond. (iii) temperature 298 K
The halogenoalkanes are hydrolysed by water, which pressure 1 Atmosphere
acts as the nucleophile. An equation for this reaction
is shown below
CH3CH2Cl + H2O → CH3CH2OH + HCl
The chloride ion then reacts with silver nitrate as
shown.
Ag+(aq) + Cl–(aq) → AgCl(s)
white ppt.
(c) (i) Q = mc DT
6C(s) + 7H2(g) Q = 200 × 4.18 × 50.3
= 42050 J
DH =
–199 kJ mol–1 = 42.1 kJ
1.00
C6H14(l)
(ii) amount of C3H8 = _____
= 0.0227 mol
44
–42.1
(iii) DH = _______
= –1850 kJ mol–1
0.0227
4 (a) (i) E
nergy is needed to break bonds
Reaction pathway
Bond breaking is endothermic
(c) DH ? (ii) T he energy required to break one mole of bonds
C(s) + 2H2(g) CH4(g)
in a gaseous substance to form gaseous atoms.
(–394) + –890 DH – 890 = –394 + 2 –286 Reaction occurs in gas phase.
(–286 2) (iii) Bonds broken
DH = –76 kJ mol–1
3 C–H 3 x 410 = 1230
CO2 + 2H2O C–O 1 x 336 = 336
1652 O–H 1 x 465 = 465
–H = + _____
(d) (i) C = + 413 kJ mol–1
4 1½ O=O 1½ x 500 = 750
(ii) H H +2781 kJ mol–1
6 + 413 = 2478 Bonds formed
H C C H
C C = 2825 – 2478 4x OH = 4 x 465 = 1860
2 C=O = 2 x 810 = 1620
H H
3470 kJ mol–1
+347 kJ mol–1
+2781 – 3470 = −689 kJ mol–1
2 (a) W
hen a system in equilibrium is subject to a change
(iv) A ctual bond enthalpies may be different from
the system readjusts itself to minimise the change
average bond enthalpy values
that has been made.
Under standard conditions, methanol is a liquid
(b) (i) A
decrease of pressure will cause the equilibrium
(b) (i) Increasing the temperature. The position of
to move to the side with the larger number of gas
equilibrium moves to the left as the forward
molecules to oppose the change. Equilibrium
reaction is exothermic.
moves left so more X2 and Y2 present.
There will be more CO and H2 produced.
(ii) A decrease in pressure means these are the
Increasing the pressure. There will be less CO
same number of molecules in a greater volume
and H2. With an increase in pressure, the position
hence the molecules collide less often and the
of equilibrium moves to the right to the side with
rate of reaction will decrease.
the least number of molecules.
(c) (i) 1
7%
(ii) Increasing the pressure means there are the
(ii) A s the temperature increases the rate of
same number of molecules in less volume so rate
conversion of reactants into products decreases.
increases as there are more collisions.
The position of equilibrium therefore must move
(iii) N one – as it speeds up the forward and reverse
to the left. This is consistent with an exothermic
reaction equally.
reaction.
5 (a) T
he enthalpy change when one mole of substance is
(d) (i) A
catalyst increases the rate of the reaction
formed from its elements under standard conditions.
because more collisions have energy exceeding
(b) C (s) + 2H2(g) → CH4(g)
the lowered Ea.
(ii) N o change
Forward and reverse reactions are changed by
the same amount.