1.	(a)	(i)	C6H6 + HNO3 ® C6H5NO2 + H2O  (1)	1
(ii)	(concentrated) sulphuric acid  (1)	1
(accept H2SO4 but give 0 marks for dilute / (aq))
(iii)	NO2+  (1)	1
(b)	(i)	Cl2 ® 2Cl· / ½ Cl2 ® Cl·  (1)	1
(ii)	Cl·+ C6H5CH3 ® C6H5CH2· + HCl  (1)
C6H5CH2· + Cl2 ® Cl· + C6H5CH2Cl  (1)	2
(iii)	C6H5CHCl2 / C6H5CCl3 / C6H5 CHCHC6 H5 /
other correct possible answer  (1)	1
(c)	(i)	–CN adding to ethanal correctly showing curly arrow and curly arrow from
double bond in C = O
CH3CH(CN) – O–
H+ adding to above ion to form product – ignore curly arrows  (1)	3
(ii)	reaction 1 is nucleophilic  (1)
reaction 2 is electrophilic  (1)	2
	or accurate idea of why nucleophile / electrophile attacks aldehyde / alkene
including polarity
(d)	(i)	to satisfy market demand for smaller / unsaturated molecules / alkenes  (1)
		1
(ii)	eg C14H30 ® C2H4 + C12H26  (1)	1
(iii)	oxide(s) of S and their effect eg acid rain
not just pollutant or toxic  (1)	1
[15] 

2.	(a)	Step 1: 
Type of reaction  	nitration or electrophilic substitution (1)
Reagent(s) 	CHNO3 + CH2SO4 (1)
Step 3: 
Type of reaction 	reduction or amination or hydrogenation (1)
Reagent(s) 	HCl/Fe or Sn or Zn or SnCl2     H2/Ni or Cu or Pt or Pd (1)	4
 
(b)	HNO3 + 2H2SO4 ® NO (1) + H3O+ + 2HSO (1)	2
[6]

3.	(a)	Reagents	AlCl3 (1)
	C6H5CH2COCl or (C6H5CH2CO)2O (1)
Equation for formation of reactive intermediate
C6H5CH2COCl + AlCl3 ® C6H5CH2CO+ (1) AlCl (1)
Name of mechanism	electrophilic substitution (1) 
Mechanism
	8
(b)	Type of reaction 	reduction	or	hydrogenation (1)
	Reagent(s) 	NaBH4 or LiAlH4	H2/Ni or Pt or Pd (1)
	or Na/EtOH		2
(c)	Reagents	H2SO4 or H3PO4 or Al2O3 (1)
Name of mechanism	elimination (1)
	2
(d)	optical	1
(e)	Type of isomerism 	geometrical or cis-trans (1)
	Explanation 	restricted rotation or
	double bond rigid (1)	2
[15]

4.	(a)	(i)	2–methylpropanenitrile (1)
(ii)	Reagent KCN (1)
Conditions alcoholic/aq (1)
(iii)	Name of mechanism 	nucleophilicsubstitution (1)
Mechanism 	
		7
(b)	Reagents 	conc HNO3 (1)	conc H2SO4 (1)
Name of mechanism  	electrophilic substitution (1)
Equation	C6H6 + HNO3 ® C6H5NO2 + H2O
	or	C6H6 +  ® C6H5NO2 + H+ (1)	4

(c)	electron deficient C or  + C in C3H7Br (1)
attracts/attacked by nucleophiles (1)
electron rich/delocalized electrons in C6H6 (1)
repels/not attacked by nucleophiles (1)	max 3
[14] 

5.	(a)	(i)	nucleophilic addition (1)	1
(ii)	2-hydroxybutanenitrile 	condone missing hyphen (1)
(1)	2
 
(b)	(i)	CH3CH2CH2Br  +  KCN  ®  CH3CH2CH2CN  +  KBr (1)	1
	allow C3H7Br	allow C4H7N
(ii)	nucleophilic substitution / SN2 (1)	1
(c)	CN–  or NC– (1)
	lone pair of electrons on C atom (1)	2
(d)	chloromethane or CH3Cl (or Br or I) (1)
	AlCl3 / FeCl3 / AlBr3 (as reagent or condition) (1)
	anhydrous (ignore reference to temperature) (1)
	electrophilic substitution (1)	4
[11]

6.	(a)	CH3CH2CH = CH2 + AlCl3 + HCl  ®  CH3CH2HCH3  (1)
	 + AlCl4–  (1)	2
(b)	electrophilic substitution  (1)	1
(c)	alternative CH3CH2CH2CH2+  or  primary  (1)
less stable  or  1 v 2 inductive effects  (1)
than CH3CH2HCH3  or  secondary  (1)	3
(d)	protonation gives CH3CH2HCH3 only  (1)
or  but–2–ene symmetrical	1
(e)	CH3CH2CH3  (1)
	or Br	1
[8]

7.	(a)	(i)	CH3COCl  or  (CH3CO)2O  (1)
AlCl3  (1)
(ii)	reduction   or   hydrogenation  (1)
(iii)	NaBH4  or  LiAlH4  or  Na/C2H5OH     or     H2/Ni  (1)
    (or  H2/Ni) 
(iv)	elimination    or    dehydration  (1)
H2SO4  or  H3PO4    or    hot Al2O3  (1)
		6
(b)	(i)	poly(phenylethene)   or   polystyrene  (1)
(ii)	CH3CH2+    or    C2H5+  (1)
CH2 = CH2 + HCl + AlCl3  ®  CH3CH2+AlCl4–  (1)
(iii)	elimination   or   dehydrogenation  (1)	4
[10]

8.	(a)	Mechanism

Allow C3H7 if structure shown elsewhere
penalise HCN splitting if wrong
	Name of product: 2-hydroxypenta(ne/o)nitrile (1)	5
	or 1-cyanobutan-1-ol
(b)	Mechanism

	Name of organic product: methylpropanoate (1)	5

(c)	(i)	([) CH3CO (])+ (1)
(ii)		4

	Notes
(abc)	extra curly arrows are penalised
(a)	be lenient on position of negative sign on : CN– but arrow must come from 1p
(a/b)	 alone loses M2 but can score M1 for attack on C+, similarly 
(a)	allow 2-hydroxypentanonitrile or 2-hydroxypenta(ne)nitrile ... pentylnitrile
(b)	in M4, allow extra: Cl– attack on H, showing loss of H+
(c)	(i)	allow formula in an “equation”(balanced or not)
be lenient on the position of the + on the formula
(ii)	for M1 the arrow must go to the C or  the + on the C
don’t be too harsh about the horseshoe, but + must not be close to the saturated C
M3 must be final step not earlier; allow M3 even if structure (M2) is wrong
[14]
	Organic points
(1)	Curly arrows: must show movement of a pair of electrons,
i.e. from bond to atom or from lp to atom / space
e.g.
 
(2)	Structures
penalise sticks (i.e. ) once per paper

Penalise once per paper
	allow CH3– or –CH3 or  or CH3
    or   H3C–
 
9.	(a)	Step 1
acylation or electrophilic substitution  (1)
A1C13  (1) CH3CH2COCl or (CH3CH2CO)2O  (1)
Step 2
reduction or hydrogenation  (1)
NaBH4 or hiA1H4 or Na/C2H5OH        H2/N1or Pt or Pd  (1)
Step 3
dehydration or elimination  (1)
H2SO4 or H3PO4 or A12O3  (1)	7
 
(b)	optical  (1)	1 
(c)	geometrical or cis-trans isomers  (1)
due to restricted rotation  (1)	2
(d)	(i)

(ii)	electrophilic addition  (1)
(iii)	C6H5 H CH2CH3  (1) 	C6H5CH2H CH3  (1)
both secondary but one is more stable  (1)	6
[16]

10.	(a)	dimethylamine	1 
(b)	nucleophilic substitution	1
	4
(c)	quaternary ammonium salt	1
(cationic) surfactant / bactericide / detergent / fabric softener or conditioner/
hair conditioner	1

(d)	

(allow CH3COOH or CH3COO– NH4+)	2
[10]
 
11.	(a)	Nucleophilic substitution	1
	4
	M1, M2 and M4 for arrows, M3 for structure of cation
(Allow M2 alone first, i.e. SN1 formation of carbocation)
(Penalise M4 if Br– used to remove H+) 
(b)	Step 1	CH3CH2CH2CN	1
	CH3CH2CH2Br + KCN ® CH3CH2CH2CN + KBr balanced	1
		(or CN–) (or Br–)
		(not HCN)	1
Step 2	CH3CH2CH2CN + 2H2 ® CH3CH2CH2CH2NH2	1
	(or 4[H])
(c)	(i)	Lone pair (on N) (in correct context)	1
R group increases electron density / donates electrons /pushes
electrons / has positive inductive effect	1
(ii)	Any strong acid (but not concentrated)
or any amine salt or ammonium salt of a strong acid	1
(d)	CH3CH2N(CH3)2	1
[12]

12.	(a)	(i)	chloromethane, any halogenomethane (correct formula accepted) (1)
aluminium chloride / Fe / FeCl3 /BF3 (1)
anhydrous (1)	3
(ii)	electrophilic (1)
substitution (1)	2
 
(b)	
and other correct products	3
penalise C6H5 once only
(c)	(i)	reduction / redox (1)	1
(ii)		2
cation only, give 2
only phenylamine, give
salt correct with charges omitted, give 2 
(d)	(i)	
(1)
reduction / redox / hydrogenation / addition not electrophilic addition (1)	2
(ii)	
oxidation /redox (1)	2 
(iii)	
		(1)
addition not electrophilic addition (1)	2
[17]

13.	(a)	CHNO3 + CH2SO4  (1)
HNO3 + 2H2SO4 ® NO (1) + H3O+ + 2HSO (1)
electrophilic substitution  (1)
	7
(b)	reduction	or 	hydrogenation  (1)
HC1/Fe or Sn or Zn or Sn Cl2		H2/Ni or Pt or Pd or Cu  (1)	2
(c)	C6H5NH2 + CH3 COCl  (1) ® C6H5NHCOCH3 + HCl  (1)
or C6H5NH2 + (CH3CO)2O ® C6H5NH COCH3 + CH3 COOH
nucleophilic addition-elemination  (1)
	7
[16]
 
14.	(a)	lone pair on N  (1)
donated to H+ or proton acceptor  (1)	2 
(b)	lone pair on N less available  (1)
due to delocatisation  (1)	2
(c)	(i)	nucleophilic substitution  (1)
(ii)	(CH3)2 NH  (1)
(CH3)3 N  (1)
(CH3)4 N+ Br–  (1)
(iii)	quaternary ammonium salt  (1)	5
[9]

15.	(a)	(i)	CH3CN + 4[H] (or  2H2)  ®  CH3CH2NH2  (1)
(ii)	LiAlH4  or  Na/C2H5OH  (or  H2/Ni)  (1)	2
(b)	(nucleophilic) substitution  or  alkylation  (1)
	Product 1	Product 2	Product 3
(C2H5)2NH	(C2H5)3N	(C2H5)4N+Br–
   (1) 		(1) 	(1)	4
 
(c)		3
(d)	lone pair on N less available
or electron density on N decreased  (1)
due to delocalisation  (1)	2 
(e)	electron withdrawal by O or CO
or delocalisation by CO  (1)  reduces electron
density on N  or  makes N lone pair less available  (1)	2 
(f)	2C2H5NH2 + CH3COCl  (1)  ®  CH3CONHC2H5 + C2H5NH3+Cl–  (1)
(nucleopholic) addition – elimination  (1)
	7
[20]

16.	(a)	(i)	H+ or proton acceptor (1)
CH3NH2 + H2O () CH3+NH3 (+) OH– (1) 
(ii)	CH3NH3Cl or HCl (1)
Or any ammonium compound or strong acid
name or formula 
(iii)	extra OH– reacts with 
or reaction / equilibrium moves to left
or ratio salt / base remains almost constant (1)
Any 2
		5
(b)	lone pair (on N accepts H+) (1)
CH3 increases electron density (on N)
	donates / pushes electrons
	has positive inductive effect (1)	2
(c)	nucleophilic substitution (1)
 (1)	2
[9]

17.	(a)	(i)	Equation 		C6H5CH2Br + 2NH3 ® C6H5CH2NH2 + NH4Br (1)
		(1)
Type of reaction 	nucleophilic subsn  or alkylation  (1)
Explanation  		further substitution occurs  (1)
		o give a mixture of products  (1) 
(ii)	reduction  or  hydrogenation  (1)
C6H5CN + 4[H] ® C6H5CH2NH2  (1)
	or 2H2
Na/C2H5OH  or  LiAlH4  or  H2/Ni  (1)
only one product formed  (1)
or avoids further substitution	9
(b)	Weaker 	base phenylamine  (1)
Explanation 	lone pair on N less available  or  electron density on
                               N lowered  (1)
	due to delocalisation  or  overlap  (1)	3
[12]

18.	(a)	(i)	cHNO3 + cH2SO4  (1)
HNO3 + 2H2SO4  ®  NO2+  (1)  + H3O+ + 2HSO4–  (1)
(ii)	electrophilic substitution  (1)
	7 
(b)	Type of reaction     reduction  (1)  not hydrogenation
Reagent(s)     NaBH4  or  Na/C2H5OH  (1)  not  LiAlH4
                                                              not  H2/Ni	2
(c)	Reagent     CH3COCl  or  (CH3CO)2O  (1)
Name of mechanism     (nucleophilic addition–elimination  (1)
Mechanism
	6
(d)	Type of reaction     reduction  or  hydrogenation  (1)
Reagent(s)     HCl/Fe  or  Sn  or  Zn     H2/Ni  or  Pt  or  Pd  (1)
	or  SnCl2  or  Ni/H2
not LiAlH4	2

(e)	optical  (1)	1
[18]

19.	(a)	(i)	lone pair on N  (1)
(ii)	inductive effect of CH3  or  electron donation  (1)
increases electron density on N
or  lone pair more available  (1)
(iii)	electron density on N decreased
or  lone pair less available  (1)
due to delocalisation  (1)	5 
(b)	(i)	Equation     CH3CH2CN + 2H2  ®  CH3CH2CH2NH2  (1)
Catalyst     Ni  (1)
(ii)	nucleophilic substitution  (1)
(iii)	further reaction can occur  (1)
between propylamine and 1-bromopropane  (1)	5
(c)	CH3CH2CH2NHCOCH3  (1)	1
(d)	Type of product     quaternary ammonium salt  or chloride  (1)
Structural formula
CH3(CH2)11N+(CH3)3  (1)
          Cl–  (1)	3
[14]

20.	(a)	Lone pair on nitrogen (1) less available or
electron density lowered (1) due to delocalisation or
resonance or mesomerism or part of x bond (1)	3 
(b)	Equation 	C6H11Br + 2NH3 ® C6H11NH2 + NH4Br (1)
Name of mechanism 	nucleophilic substitution (1)
Mechanism
	6 
(c)	(i)	NaCN or KCN (1)
(ii)	Reagent(s) 	Na/C2H5OH or LiAlH4 or H2/Ni (1)
Type of reaction 	reduction or hydrogenation (1)
	Equation 	C6H11CN + 4[H] ® C6H11CH2NH2 (1)
	or 2H2 if hydrogenation	4

(d)	Equation 	2RNH2 + CH3COCl ® RNHCOCH3 (1) + RNH3Cl (1)
Name of mechanism 	(nucleophilic) addition-elimination (1)
Mechanism 
	7
[20]

21.	(a)	(i)	suitable graphical formula for ethanoic anhydride  (1)	1
(ii)	(acid) anhydride  (1)	1
 
(b)	(i)	F = ethylamine / aminoethane  (1)	1
(ii)	reduction or hydrogenation or addition (ignore reference
to mechanism)  (1)
		1 
(c)	CH3COCl  +  CH3CH2NH2  ®  CH3CONHCH2CH3  +  HCl
	CH3CONHCH2CH3  (1)
	balanced  (1)	2
[6]
 
22.	(a)	Lone pair on N or electron density on N (1)
more available or electron density increased (1)
electron donation or inductive effect (1)	3 
(b)	Reagent(s)	LiAlH4 or Na/EtOH or H2/Ni (1)
Type of reaction	reduction or hydrogenation (1)
Equation	CH3CN + 4[H] or 2H2 ® CH3CH2NH2 (1)	3
(c)	(C2H5)4N+Br– (1)
quaternary ammonium salt (1)
	cationic surfactant (1)
or fabric softener	3
 
(d)	Name of mechanism	addition-elimination (1)
Mechanism
	5
 
(e)	C2H5NH2 + (CH3CO)2O ® C2H5NHCOCH3 + CH3COOH (1)
or 2C2H5NH2 + (CH3CO)2O ® C2H5NHCOCH3 + CH3COO–H3C2H5	1
[15]

23.	(a)	(nucleophilic) addition-elimination;	1

(M3 for structure)
(M4 for 3 arrows and lone pair)
(M2 not allowed independent of M1, but allow M1 for correct attack
on C+ if M2 show as independent first.)
(+on C of C=O loses M2 but ignore d+ if correct)
(Cl– removing Ft loses M4) 
	5
(If MS lost above for wrong C chain, do not penalise same error again here)
(b)	CH3CH2COCl + AlCl3 ® [CH3CH2CO]+ + AlCl4–;	1
(penalise wrong alkyl group once at first error)
(position of + on electrophile can be on O or C or outside [ ]) (penalise wrong curly arrow in the equation or lone pair on AlCl3)

(M1 arrow from within hexagon to C or to + on C)
(don’t penalise position of + on C of RCO+)	(horseshoe must not extend beyond C2 to C6 but can be smaller)
(+ not too close to C1)
(penalise M2 if CH3 chain wrong again but allow M1 and M3)
(M3 arrow into hexagon unless Kekule)
(allow M3 arrow independent of M2 structure)	
		3
		1
(or can be gained in mechanism);

(c)	M1 CH3CH2COCl + H2O → CH3CH2COOH + HCl 1	1
(penalise wrong alkyl group once at first error)
	M2 Mr of CH3CH2COCl = 92.5 1	1
(if Mr wrong, penalise M2 only)
	M3 moles of CH3CH2COCl = 1.48/92.5 = 0.016 1	1
	M4 moles NaOH = 2 × 0.016 = 0.032 1	1
(allow for × 2 conseq to wrong no of moles)
	M5 volume of NaOH = 0.032/0.42 = 0.0762 dm3 or 76.2 cm3 1
(with correct units)
(if ×2 missed in M4 lose M5 also)	1
[16]

24.	(a)	CH3COCl  +  AlCl3  ®  CH3O  +  AlCl 	1
	equation	1
	penalise wrong alkyl group once at first error
position of + on electrophile can be on O or C or outside [ ]
penalise wrong curly arrow in the equation or lone pair on AlCl3  else ignore
	Electrophilic_substitution	1
NOT F/C acylation

horseshoe must not extend beyond C2 to C6 but can be smaller 
+ not too close to C1
M3 arrow into hexagon unless Kekule
allow M3 arrow independent of M2 structure
	M1 arrow from within hexagon to C or to + on C 
+ must be on C of 	3

(b)	Nucleophilic_addition	NOT reduction	1

	4
M2 not allowed independent, but can allow M1 for attack of H– on C+ formed
	1–phenylethan(–1–)ol or (1–hydroxyethyl)benzene	1
 
(c)	dehydration or elimination	1
(conc) H2SO4 or (conc) H3PO4 	1
allow dilute and Al2O3 
Do not allow iron oxides
[14]

25.	(a)	ethyl benzene	1
chloroethane or bromoethane (or ethene and hydrogen chloride/bromide)	1
aluminium chloride/bromide or iron(III) chloride /bromide or iron +
chorine/bromine	1
CH3CH2Cl + AlCl3 → CH3CH2+ + AlCl4–	1
electrophilic substitution	1

		3 
(b)		1

CH3CH2COCl / propanoyl chloride or (CH3CH2CO)2O / propanoic anhydride	1
NaBH4 or LiAlH4 or H2/Ni (not Sn/Fe with HCl)	1
[11]

26.	X is CH3CN or ethanenitrile or ethanonitrile or methyl cyanide or	1
cyanomethane or ethyl nitrile or methanecarbonitrile
Not ethanitrile
but contradiciton of name and structure lose marks
	Y is CH3CH2NH2 or ethylamine or aminoethane or ethanamine	1
	Step 1: reagent	KCN not HCN/HCl	1
	 condition	(aq)/alcohol - only allow condition if reagent
	correct or incomplete	1
	Step 2: reagent	H2	LiAlH4	Na	Zn/Fe/Sn	Not NaBH4	1
	 condition	Ni/Pt/Pd	ether	ethanol	HCl		1
 
	Z is an amine or aminoalkane or named amine even if incorrect name for Z	1
	secondary (only award if amine correct)
   (Br–) + can be on N or outside brackets as shown	1
	nucleophilic substitution	1
[9]
27.	(a)	Cyclohexane evolves 120 kJ mol–1
\ (expect triene to evole) 360 kJ mol–1 (1) or 3 × 120
360 – 208 = 152 kJ (1) NOT 150	4
152 can score first 2
QofL:	benzene lower in energy / more (stated) stable (1)
Not award if mentions energy required for bond breaking
	due to delocalisation (1) or explained

(b)	(i)	phenylamine weaker (1)
if wrong no marks
	lone pair on N (less available) (1)
delocalised into ring (1) or “explained”	3 
(ii)	addition – elimination (1)

structure (1) M3
3 arrows (1) M4
N-phenyl ethanamide (1)	6 
(iii)	conc HNO3 (1)
conc H2SO4 (1)
HNO3 + 2H2SO4 ® O2 + H3O+ + 2HSO4– (1)
	6
(iv)	peptide / amide (1)
NaOH (aq) (1)	2
HCl conc or dil or neither
H2SO4 dil NOT conc
NOT just H2O

Notes
(a)	·	360 or 3 × 120 or in words (1);
·	152 NOT 150 (1);    (152 can get first two marks)
·	Q of L benzene more  stable but not award if DH values used to say
that more energy is required by benzene for hydrogenation compared with
the triene or if benzene is only compared with cyclohexene (1);
·	delocalisation or explained (1)
(b)	(ii)	or N-phenylacetamide or acetanilide
mechanism:  if shown as substitution can only gain M1
if CH3CO+ formed can only gain M1
lose M4 if Cl– removes H+
be lenient with structures for M1 and M2 but must be correct for M3
 alone loses M2
(iii)	No marks for name of mechanism in this part
if conc missing can score one for both acids (or in equation)
allow two equations
allow HNO3 + H2SO4 ® NO2+ + HSO4– + H2O
ignore side chain in mechanism even if wrong
arrow for M1 must come from niside hexagon
arrow to NO2+ must go to N but be lenient over position of +
+ must not be too near “tetrahedral” Carbon
horseshoe from carbons 2-6 but don’t be too harsh 
(iv)	reagent allow NaOH
HCl conc or dil or neither
H2SO4 dil or neither but not conc
not just H2O
[21]