1.
2-Methylpropan-2-ol
ALLOW methylpropan-2-ol
[1]
2.
(i)
Same molecular formula but different structural formulae
ALLOW Same molecular formula but different arrangement of
atoms
OR Same molecular formula but different structures
OR Same molecular formula but different displayed formulae
DO NOT ALLOW Same molecular formula but different spatial
arrangement of atoms
1
(ii)
CH3CH2CH2CH2OH OR (CH3)2CHCH2OH
ALLOW
OH
OH
OR
ALLOW displayed formula
ALLOW sticks (i.e. no H shown bonded to C)
ALLOW
DO NOT ALLOW
OH shown as below
C
C
C
C
OH
sticks OK and –OH is OK
OH
C
C
C
C
sticks OK and OH– is not OK
ALLOW correct ethers
1
[2]
3.
(i)
(sum of) the molecular masses of the desired product ÷
sum of molecular masses of all products
× 100
ALLOW (sum of) the molecular masses of the desired
product ÷
sum of molecular masses of all reactants
× 100
1
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(ii)
this preparation is addition OR has 100% atom economy OR
there is only one product
preparation from cyclohexanol has less than100% atom
economy OR H2O is produced as well OR calculated atom
economy = 82%
ALLOW no by products formed
ALLOW other substances formed OR cyclohexene is not
the only product
2
[3]
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4.
(a)
(i)
H
H
C2 H 5
δ+
C
I
δ
C2H5
H
C
OH +
I–
H
OH–
C–I curly arrow from the bond not from carbon atom
curly arrow from the OHcorrect partial charges on C—I
no need to show any lone pairs on oxygen but must have a clear
negative sign rather than partial negative charge
IGNORE lone pairs
IGNORE products of this reaction
ALLOW curly arrow from a negative charge or from any part of
hydroxide ion
If SN1 mechanism is given then use the mark scheme below
correct partial charges on C—I
C–I curly arrow from the bond not from carbon atom
curly arrow from the OH- to the correct carbocation
H
C2H 5
C
δ+
δ
H
H
C2H5
C+
OH–
H
3
(ii)
nucleophilic substitution
1
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(b)
C–I bonds broken more easily
C–I bonds are weaker OR have less bond enthalpy OR C–I
bonds are longer
ALLOW ora e.g. C—Br bonds are stronger OR broken
less easily
2
[6]
5.
Structural isomer
compounds with the same molecular formula
different structural formulae
but with
Stereoisomer
compounds with the same structural formula
different arrangements in space
but with
Evidence of using Mr of 70 to calculate molecular formula of C5H10
F and G are
o
Correct identification of the E and Z isomers
H is
E/Z happens because
double bonds restricts rotation
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different groups on each carbon of the double bond
ALLOW same molecular formula
but different
structures
Second marking point is DEPENDENT on first mark
ALLOW compounds with the same structure
Second marking point is DEPENDENT on first mark
This is the QWC mark
IGNORE wrong names of F, G and H
ALLOW structural or displayed formulae for F, G and H
e.g. H is CH3CH2CH2CHCH2
ALLOW identification using trans and cis and
ALLOW this marking point as identification of another example
of identifying E/Z or cis and trans if not done for F and G
ALLOW one mark if no structures drawn but correct names
given for F, G and H i.e E-pent-2-ene, Z-pent-2-ene and
pent-1-ene
ALLOW ecf on structures if wrong molecular formula used or
consistent error or slip such as having just sticks
[11]
6.
(i)
species with an unpaired electron (1)
1
(ii)
uv (light)/high temperature/min of 400° C/sunlight (1)
1
(iii)
homolytic (fission) (1)
1
(iv)
C4H10 + Cl• (1)  C4H9• + HCl (1)
C4H9• + Cl2 (1)  C4H9Cl + Cl• (1)
2
[5]
7.
(a)
(i)
uv/sunlight/high temperature (range 400  700 C)
1
(ii)
Cl2  2Cl
1
C4H10  Cl  HCl  C4H9/C4H9
1
C4H9/C4H9 Cl2  C4H9Cl  Cl
1
(iii)
any two free radicals from (a) (ii)
1
(iv)
homolytic (fission)
1
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(b)
(i)
2, 3-dichlorobutane
(ii)
1
1
Cl
Cl
(iii)
any dichlorobutane except 2,3-dichlorobutane.
1
[9]
8.
(a)
(i)
(ii)
(b)
(volatile components) can escape/distil out (1)
ethanal is most volatile/bpt less than 60 °C/partial oxidation (1)
2
(volatile components) cannot escape/ refluxed (1)
complete oxidation will be achieved/oxidised to the acid (1)
2
C2H5OH + 2[O]  CH3COOH + H2O
C2H5OH, 2[O] and CH3COOH (1)
rest of equation (1)
2
[6]
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