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1
AS: 2812
January 2001
Chains and Rings Mark Scheme
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2 1. (a) (i) OH/hydroxy/hydroxyl/ROH (ii) CnH2n+1OH (iii) C7H15OH / C7H16O
(b)
88.
(c)(i) 1 mark for plotting the points 1 mark for the line extended to enable [Link] of C8H17OH to be estimated. 115 -125 oC 190 -205 oC
(ii)
I II
butan-1-ol C8H17OH
(ii)
Boiling point increases as the Mr increases/ proportional to Mr .
[Total : 9]
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3 2 (a) contains carbon and hydrogen only
separates due to differences in boiling point
(b)
works out/uses Mr = 156 (ii) 132/156 method mark 84.6% C C9H20
(c)
C11H24 Ethene
+ C 2 H4
(d)
(i)
Draw the isomers of pentane.
H H3C C
H C H
H C H
H3C
H C
CH3
CH3
CH3
CH3 Isomer C
H3C
CH CH3 3
Isomer B
Isomer D
(ii)
D, C, B to match as drawn in (d)(i)
(iii)
less van der Waals' forces in D/ as chain length increases so does b pt./greater the branching~lower the boiling point C5H12 + 8O2
(iv)
5CO2
+ 6H2O
(CO2 + H2O gets ) (v) branched chains burn more efficiently/ add it to petrol
[Total : 16]
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3 (a) Initiation Propation 1 Propagation 2 Termination Cl2 2Cl 4
[4]
C3H8 + Cl HCl + C3H7 C3H7 + Cl2 C3H7Cl + Cl Any two free radicals
(b) (i) (ii)
Compound H = 1,2-dichloropropane 1 mark for each correct structure
H H Cl H C C C Cl H H H or Cl
H H H
H Cl H
C C C Cl or H C C C H H H H H Cl H
(c) (i)
(ii)
water OH- behaves as a nucleophile
OH- has a lone pair of electrons/ seeks out electron deficient areas/attracted to C+ (d) (i) reflux is the continuous process of evaporation followed by condensation/ description of what would be seen to indicate that the process is continuous orange to green (iii)
C3H7OH/C3H8O + 2[O] C2H5COOH/C3H6O2 + H2O
(ii)
(All three formulae correct gets one mark) (e) wavenumber bond wavenumber bond 1680 1750 cm-1 C=O 2500 3300 cm-1 O-H
[Total : 19]
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5 4 (a)
H H H H H H H C C C H H
1 mark
H C C C H + H Br
1 mark for either carbonium ion
H H H H C C C H H Br Br
H H H H C C C H + H Br
1 mark
Br : Br
1 mark for (temp induced) dipole in the Br-Br
[4]
.. Br-
Additional 1 mark if curly arrow starts at the lone pair
5 marking points for max of 4 marks
(b) (ii) reagent = H2 conditions = Ni/Pt as catalyst (iii)
(i)
H H H H C C C H H H OH and
H H H H C C C H H OH H
(c)
(i)
Addition polymer
(ii)
H CH3H CH3 C C C C H H H H
(iii)
non-biodegradeable or words to that effect when burnt they release toxic fumes
[Total : 13]
(a)
(i)
C4H9OH/C4H10O
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6
(ii)
C4H9OH/C4H10O
+ HCl
C4H9Cl
H2 O
(b)
The upper layer because the organic compounds have a lower density than water.
(c)
(i) (ii)
CO2 HCl
(d)
(i)
51 oC
[Total : 9]
(ii) (iii) (iv)
4/74 = 0.05(4) 3.75/92.5 = 0.04(1) 75% (allow 80% if (d) (ii) given as 0.05 / mark ecf for (d)(ii)/(d)(i) *100)
(a)
functional group 1 test observation
alkene add bromine decolourised
functional group 2 test observation
alcohol Na/ PCl5/ white fumes/HCl RCO2H smell
bubbles/H2
[6]
(b)
H H CH3 H3 C C C C C C H H H Compound F
O H
[1] [Total : 7]
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7
7 Fermentation
Yeast/enzyme Temperature about 30 oC C6H12O6 2C2H5OH Batch process + 2CO2
Hydration of ethene. Reagent Temp/press Catalyst steam/water at > 100 oC 300 oC & 70 100 atm phosphoric acid
C2H4 + H2O C2H5OH Continuous process
1 mark available for Quality of written communication.. base the award of the mark on the ability to communicate the essential chemistry
[Total : 12 max = 9]
8 Ethane saturated/single bonds only/ -bond `
tetrahedron 109o 28' unsaturated/double bonds/contains a -bond draws or explains overlap of adjacent p-orbitals at right angle to the plane of the molecule trigonal planar approx 120o
Ethene
1 mark available for Quality of written communication ... base the award of the mark on the ability to use essential technical language such as saturated/unstaurated/tetrahedron, trigonal planar/ overlap of adjacent p-orbitals [Total : 8]
