1.	C
[1]

2.	E: primary and F: secondary;
G: primary;
G / E: only one alkyl group/2 H atoms attached to the carbon atom
attached to the Cl / only one carbon atom attached to the carbon atom
attached to the Cl;
F: two alkyl groups/1 H atom attached to the carbon atom attached to
the Cl / two carbon atoms attached to the carbon atom attached to the Cl;	4
[4]

3.	(a)	boiling points increase (from the first member to the fifth member);
increasing size of molecule/area of contact/number of electrons (from
the first to the fifth member);
strength of intermolecular/van der Waals’/London/dispersion forces
increase / more energy required to break the intermolecular bonds
(from first member to fifth member);	3
 
(b)	same general formula;
successive members differ by CH2;
same functional group / similar/same chemical properties;
gradual change in physical properties;	2 max
Accept specific physical property such as melting point, boiling
point only once.
[5]

4.	B
[1]

5.	B
[1]

6.	C
[1]

7.	A
[1]

8.	(a)	(i)
Isomer	A	B	C	
Boiling point	36 °C	28 °C	10 °C	
	Award [1] if correct boiling points are assigned to 3 isomers.
	increase in branching / more side chains / more spherical shape /
reduced surface contact / less closely packed;
weaker intermolecular force/van der Waals’/London/dispersion forces;
Accept the opposite arguments	3
 
(ii)	B: 2-methylbutane/methylbutane;
C: 2,2-dimethyl propane/dimethyl propane;
Do not penalize missing commas, hyphens or added spaces.
Do not accept 2-dimethylpropane, or 2,2-methylpropane.	2
 
(b)	C5H12;
Accept any two of the following explanations.
	C5H11OH has greater molar mass / produces less grams of CO2 and
H2O per gram of the compound / suitable calculations to show this;
C5H11OH contains an O atom which contributes nothing to the energy
released / partially oxidized / OWTTE;
analogous compounds such as butane and butan-1-ol show a lower
value for the alcohol per mole in the data book / OWTTE;
the total bond strength in the pentanol molecule is higher than the total
bond strength in pentane;
the total amount of energy produced in bond formation of the products
per mole is the same;
fewer moles of pentanol in 1 g;
pentanol requires more energy to break intermolecular forces/
hydrogen bonding / OWTTE;	3 max
[8]

9.	(i)	(Empirical formula =) C8H8O3;
	2
Allow double bonds on arene in alternate positions, or allow delocalized representation (of pi electrons).

(ii)	the bond at 0.1373 nm is a double bond and the bond at 0.1424 nm is a
single bond;
in CO2(g) both bonds are double bonds and would have a value
around 0.137 nm;	2
 
(iii)	Ester;
Arene/benzene ring;
Alcohol;	2
Award [2] for any three correct, award [1] for any two correct.
Do not accept alkane as a type of functional group in this molecule.
[6]

10.	Initiation:
Cl2  2Cl•;
Reference to UV/hf/hν/heat must be included.
	Propagation:
Cl• + CH4 → CH3• + HCl;
CH3• + Cl2 → CH3Cl + Cl•;
	Termination:
Cl• + Cl• → Cl2 / CH3• + Cl• → CH3Cl / CH3• + CH3• → C2H6;	4
Allow representation of radical without • (e.g. Cl, CH3) if consistent
throughout mechanism.
If representation of radical (i.e. •) is inconsistent, penalize once only.
[4]

11.	D
[1]

12.	B
[1]

13.	C
[1]

14.	(i)	boiling point increases as the number of carbons increases / OWTTE;
Greater Mr and hence greater van der Waals’/London/dispersion
forces present;	2
 
(ii)	CH4 + Cl2 CH3Cl + HCl;
Do not award mark if hv/uv light is not given.
	Initiation step:
Cl2  2Cl•;
Do not award mark if hv/uv light is not given.
Penalize once only.
	Propagation step:
CH4 + Cl• → CH3• + HCl;
CH3• + Cl2 → CH3Cl + Cl•;
Termination step:
Cl• + Cl• ® Cl2 or Cl• + CH3• ® CH3Cl or CH3• + CH3• → CH3CH3;	5
Allow fish-hook half-arrow representations i.e. use of .
Penalize use of full curly arrows once only.
Penalize missing dots on radicals once only.
[7]

15.	C
[1]

16.	A:

B:

C:

	1,2-dichloroethane;
D:

	Accept condensed formulas.	5
Penalize missing hydrogens only once.
[5]

17.	(i)	addition of bromine/bromine water;
the bromine colour remains with propane and propene
decolourizes the bromine / solution changes from brown to colourless;	2
Do not accept “clear” instead of “colourless”.
 
(ii)	addition (polymerization);
 ( CH(CH3)–CH2 )  / –CH(CH3)CH2–;	2
Continuation bonds necessary for mark, displayed formula or
condensed structural formula can be given.
Accept if more than one repeating unit is shown.

(iii)	hydrogenation (of vegetable oils) / manufacture of margarine /
manufacture of ethanol / addition of water;	1
Accept manufacture of alcohol.
Do not accept hydrogenation of alkenes.
[6]

18.	A
[1]

19.	B
[1]

20.	

	Accept condensed formulas.	5
Award [1 max] if A and D are other way round (and nothing else correct).
Award [2 max] if A and D are other way round but one substitution product
B or E is correct based on initial choice of A and D.
Award [3 max] if A and D are other way round but both substitution
products B and E are correct based on initial choice of A and D.
M2 (for B) and M5 (for E) may also be scored for substitution product
if primary chloroalkane used.
Penalize missing hydrogens once only.
[5]

21.	(a)	(i)	A: butan-1-ol;
B: butan-2-ol;
C: (2-)methylpropan-2-ol;
D: (2-)methylpropan-1-ol;
Accept answers in the form of 1-butanol and 2-methyl-2-propanol etc.
Penalize incorrect punctuation, e.g. commas for hyphens, only once.	4
 
(ii)	C/(2-)methylpropan-2-ol;	1
 
(iii)	A/butan-1-ol;	1
 
(iv)	B/butan-2-ol;	1
 
(v)
	1
 
(b)	(i)	SN2;	1

(ii)

	curly arrow going from lone pair/negative charge on O in OH– to C;
Do not allow curly arrow originating on H in OH–.
	curly arrow showing Br leaving;
Accept curly arrow either going from bond between C and Br to Br in
1-bromobutane or in the transition state.
	representation of transition state showing negative charge, square
brackets and partial bonds;
Do not penalize if HO and Br are not at 180° to each other.
Do not award third mark if OH----C bond is represented.	3
[12]

22.	(i)	CH3CH2CH2OH, propan-1-ol/1-propanol;
CH3CH(OH)CH , propan-2-ol/2-propanol;
Need both formula and name for mark.
Accept either condensed or full structural formulas.
	CH3CH2CH2OH: primary and CH3CH(OH)CH3: secondary;	3
 
(ii)	CH3CH2CHO;
CH3CH2COOH;
CH3COCH3;
Accept either condensed or full structural formulas.
	from propan-1-ol: CH3CH2CHO(propanal) obtained by distillation (as
product is formed);
propan-1-ol gives CH3CH2COOH (propanoic acid) by (heating under) reflux;
Award [1] if CH3CH2CHO and CH3CH2COOH identified but conditions
not given/incorrect.
	propan-2-ol gives CH3COCH3 by heat / reflux;	5 max
[8]

23.	B
[1]

24.	(i)

	curly arrow going from lone pair/negative charge on O in HO– to C;
Do not allow curly arrow originating on H in HO–.
	curly arrow showing Cl leaving;
Accept curly arrow either going from bond between C and Cl to Cl in
2-chloro-3-methylbutane or in the transition state.
	representation of transition state showing negative charge, square
brackets and partial bonds;
Do not penalize if HO and Cl are not at 180° to each other.
Do not award M3 if OH ---- C bond is represented.
	formation of organic product 3-methylbutan-2-ol and Cl–;	4
 
(ii)	OH– has a negative charge/higher electron density;
greater attraction to the carbon atom (with the partial positive
charge) / OWTTE;	2
Do not allow just greater attraction.
[6]

25.	C
[1]

26.	B
[1]

27.	(i)	Step 1:
CH2CHCl + H2 → CH3CH2Cl;
	Step 2:
CH3CH2Cl + OH– → CH3CH2OH + Cl–;
Allow NaOH or NaCl etc. instead of OH– and Cl–.
Allow abbreviated formulas C2H3Cl, C2H5Cl, C2H5OH.	2

(ii)	H2SO4/H+/acidified and Cr2O72–/(potassium/sodium) dichromate;
Accept suitable oxidizing agents (e.g. KMnO4 etc.) but only with acid.
Ignore missing or incorrect oxidation states in reagents.
	(heat under) reflux;
Second mark can be scored even if reagent is incorrect.	2
 
(iii)	CH3COOH(aq) + H2O(l)  CH3COO–(aq) + H3O+(aq)
	OR
	CH3COOH(l) + H2O(l)  CH3COO–(aq) + H3O+ (aq)
	OR
	CH3COOH(aq)  CH3COO–(aq) + H+(aq)
correct equation;
state symbols and ;
BL acid is CH3COOH and cb is CH3COO– / BL acid is H3O+ and cb is H2O;	3
[7]

28.	(i)

Penalize missing H atoms once only.	2
 
(ii)	CH3CH=CHCH3 + H2O → CH3CH(OH)CH2CH3;
concentrated sulphuric acid/ H2SO4 and heat/steam / phosphoric acid/H3PO4
(catalyst) and heat/steam;
3CH3CH(OH)CH2CH3 + Cr2O72– + 8H+ → 3CH3COCH2CH3 + 2Cr3+ + 7H2O;
Accept CH3CH(OH)CH2CH3 + [O] → CH3COCH2CH3 + H2O .
Accept C2H5 as CH2CH3.
	dichromate(VI) (ion)/Cr2O72– and acidic/H+;
Accept MnO4– in place of Cr2O72– in third and fourth marks.
	heat/reflux;	5
[7]