1.

(a) (i) C
6
H
6
+ HNO
3
C
6
H
5
NO
2
+ H
2
O (1) 1
(ii) (concentrated) sulphuric acid (1) 1
(accept H
2
SO
4
but gie ! "ar#s $or dilute % (a&))
(iii) NO
2
+
(1) 1
(b) (i) Cl
2
2Cl % ' Cl
2
Cl (1) 1
(ii) Cl+ C
6
H
5
CH
3
C
6
H
5
CH
2
+ HCl (1)
C
6
H
5
CH
2
+ Cl
2
Cl + C
6
H
5
CH
2
Cl (1) 2
(iii) C
6
H
5
CHCl
2
% C
6
H
5
CCl
3
% C
6
H
5
CHCHC
6
H
5
%
other correct possible ans(er (1) 1
(c) (i)
)
CN adding to ethanal correctl* sho(ing curl* arro( and curl* arro( $ro"
double bond in C + O
CH
3
CH(CN) ) O
)
H
+
adding to aboe ion to $or" product ) ignore curl* arro(s (1) 3
(ii) reaction 1 is nucleophilic (1)
reaction 2 is electrophilic (1) 2
or accurate idea o$ (h* nucleophile % electrophile attac#s aldeh*de % al#ene
including polarit*
(d) (i) to satis$* "ar#et de"and $or s"aller % unsaturated "olecules % al#enes (1)
1
(ii) eg C
14
H
3!
C
2
H
4
+ C
12
H
26
(1) 1
(iii) o,ide(s) o$ S and their e$$ect eg acid rain
not -ust pollutant or to,ic (1) 1
[15]
2. (a) Step 1.
Type of reaction nitration or electrophilic substitution (1)
Reagent(s) CHNO
3
+ CH
2
SO
4
(1)
Step 3.
Type of reaction reduction or a"ination or h*drogenation (1)
Reagent(s) HCl%/e or Sn or 0n or SnCl
2
H
2
%Ni or Cu or 1t or 1d (1) 4

(b) HNO
3
+ 2H
2
SO
4
NO
+
2
(1) + H
3
O
+
+ 2HSO
)
4
(1) 2
[6]
1
3. (a) Reagents AlCl
3
(1)
C
6
H
5
CH
2
COCl or (C
6
H
5
CH
2
CO)
2
O (1)
Equation for formation of reactive intermediate
C
6
H
5
CH
2
COCl + 2lCl
3
C
6
H
5
CH
2
CO
+
(1) 2lCl
)
4
(1)
Name of mechanism electrophilic substitution (1)
Mechanism
C O C H C H C O C H C H
2 2 6 6 5 5
+
+
( 1 ) ( 1 )
( 1 )
H
3
(b) Type of reaction reduction or h*drogenation (1)
Reagent(s) Na4H
4
or 5i2lH
4
H
2
%Ni or 1t or 1d (1)
or Na%6tOH 2
(c) Reagents H
2
SO
4
or H
3
1O
4
or 2l
2
O
3
(1)
Name of mechanism eli"ination (1)
2
(d) optical 1
(e) Type of isomerism geo"etrical or cis7trans (1)
Explanation restricted rotation or
double bond rigid (1) 2
[15]
4. (a) (i) 2)"eth*lpropanenitrile (1)
(ii) 8eagent 9CN (1)
Conditions alcoholic%a& (1)
(iii) Name of mechanism nucleophilic substitution (1)
Mechanism
C H C 4 r C H C C N
C H
H
C H
H
3 3
3 3
N C .
)
)
: 1 ;
: 1 ;
: 1 ;
. 4 r +
<
(b) Reagents conc HNO
3
(1) conc H
2
SO
4
(1)
Name of mechanism electrophilic substitution (1)
Equation C
6
H
6
+ HNO
3
C
6
H
5
NO
2
+ H
2
O
or C
6
H
6
+
+
2
NO
C
6
H
5
NO
2
+ H
+
(1) 4
2
(c) electron deficient C or
a
+ C in C
3
H
7
Br (1)
attracts%attac#ed b* nucleophiles (1)
electron rich%delocali=ed electrons in C
6
H
6
(1)
repels%not attac#ed b* nucleophiles (1) "a, 3
[14]
5. (a) (i) nucleophilic addition (1) 1
(ii) 27h*dro,*butanenitrile condone "issing h*phen (1)
H H H
H H H
H C C C C N
(1) 2

(b) (i) CH
3
CH
2
CH
2
4r + 9CN CH
3
CH
2
CH
2
CN + 94r (1) 1
allo( C
3
H
<
4r allo( C
4
H
<
N
(ii) nucleophilic substitution % SN2 (1) 1
(c) CN
)
or NC
)
(1)
lone pair o$ electrons on C ato" (1) 2
(d) chloro"ethane or CH
3
Cl (or 4r or >) (1)
2lCl
3
% /eCl
3
% 2l4r
3
(as reagent or condition) (1)
anh*drous (ignore re$erence to te"perature) (1)
electrophilic substitution (1) 4
[11]
6. (a) CH
3
CH
2
CH + CH
2
+ 2lCl
3
+ HCl CH
3
CH
2
+
C
HCH
3
(1)
+ 2lCl
4
)
(1) 2
(b) electrophilic substitution (1) 1
(c) alternatie CH
3
CH
2
CH
2
CH
2
+
or pri"ar* (1)
less stable or 1 2 inductie e$$ects (1)
than CH
3
CH
2
+
C HCH
3
or secondar* (1) 3
(d) protonation gies CH
3
CH
2
+
C HCH
3
onl* (1)
or but)2)ene s*""etrical 1
(e) CH
3
CH
2
C H
C l
CH
3
(1)
or 4r 1
[8]

3
7. (a) (i) CH
3
COCl or (CH
3
CO)
2
O (1)
2lCl
3
(1)
(ii) reduction or h*drogenation (1)
(iii) Na4H
4
or 5i2lH
4
or Na%C
2
H
5
OH or H
2
%Ni (1)
(or H
2
%Ni)
(i) eli"ination or deh*dration (1)
H
2
SO
4
or H
3
1O
4
or hot 2l
2
O
3
(1)
6
(b) (i) pol*(phen*lethene) or pol*st*rene (1)
(ii) CH
3
CH
2
+
or C
2
H
5
+
(1)
CH
2
+ CH
2
+ HCl + 2lCl
3
CH
3
CH
2
+
2lCl
4
)
(1)
(iii) eli"ination or deh*drogenation (1) 4
[10]
8. (a) Mechanism
( 1 )
( 1 )
( 1 )
( 1 ) O
( H )
? 1
? 3
? 2
? 4
( C H C H C H ) C C H C H C H C H C H C H C H C H
3 3 3 2 2 2 2 2 2
N C .
O . O H
C N C N
H
)
)
+
Allow
!
"
#
if structure shown elsewhere
penalise "N splitting if wrong
Name of product. 27h*dro,*penta(ne%o)nitrile (1) 5
or 17c*anobutan717ol
(b) Mechanism
( 1 )
( 1 )
O
O
O
O .
O
O C H
? 1
? 2
( C H C H ) C C l C H C H C C l C H C H C
3 3 3
3
2
3
3
2 2
( C H )
C H
H
H
@ @
@ @
+
)
( )
C l )
s t r u c t u r e ? 3
3 a r r o ( s ? 4
( 1 )
( 1 )
Name of organic product. "eth*lpropanoate (1) 5
4
(c) (i) ([) CH
3
CO (])
+
(1)
(ii) 4
( 1 )
3
3
+
+
( 1 ) ? 1
( 1 ) ? 2
C O C H
C H C O
? 3 H
Notes
(abc) e,tra curl* arro(s are penalised
(a) be lenient on position o$ negatie sign on . CN
)
but arro( "ust co"e $ro" 1p
(a%b) C O alone loses ?2 but can score ?1 $or attac# on C+A si"ilarl* C C l
(a) allo( 27h*dro,*pentanonitrile or 27h*dro,*penta(ne)nitrile @@@ pent*lnitrile
(b) in ?4A allo( e,tra. Cl
)
attac# on HA sho(ing loss o$ H
+
(c) (i) allo( $or"ula in an Be&uationC(balanced or not)
be lenient on the position o$ the + on the $or"ula
(ii) $or ?1 the arro( "ust go to the C or the + on the C
donDt be too harsh about the horseshoeA but + "ust not be close to the saturated C
?3 "ust be $inal step not earlierE allo( ?3 een i$ structure (?2) is (rong
[14]
Organic points
(1) Curl* arro(s. "ust sho( "oe"ent o$ a pair o$ electronsA
i@e@ $ro" bond to ato" or $ro" lp to ato" % space
e@g@
3 3
H N . C 4 r O 8 H N . C 4 r
8 8 H H
H H

(2) Structures
penalise stic#s (i@e@
C
) once per paper
3
2
H O C 8 o r 8 C O H o r ) N H
O H C 8 o r 8 C H O H N )
H
H
H
H
H
H
H
H
e t c
1enalise once per paper
allo( CH
3
) or )CH
3
or
3
C H
or CH
3
or H
3
C)

5
9. (a) $tep %
ac*lation or electrophilic substitution (1)
21C1
3
(1) CH
3
CH
2
COCl or (CH
3
CH
2
CO)
2
O (1)
$tep &
reduction or h*drogenation (1)
Na4H
4
or hi21H
4
or Na%C
2
H
5
OH H
2
%N1or 1t or 1d (1)
$tep !
deh*dration or eli"ination (1)
H
2
SO
4
or H
3
1O
4
or 21
2
O
3
(1) <

(b) optical (1) 1
(c) geo"etrical or cis7trans iso"ers (1)
due to restricted rotation (1) 2
(d) (i)
C H C H 4 r C H
2 2 3 3
C H 4 r C H C H
( 1 ) ( 1 )
(ii) electrophilic addition (1)
(iii) C
6
H
5

+
C
H CH
2
CH
3
(1) C
6
H
5
CH
2
+
C
H CH
3
(1)
both secondar* but one is "ore stable (1) 6
[16]
10. (a) di"eth*la"ine 1
(b) nucleophilic substitution 1
H C N H H C 4 r
?
1
2 3 3
?
2
H
H C N C H
H
+
?
3
?
4
3 3
C H N H
3 2
4
(c) &uaternar* a""oniu" salt 1
(cationic) sur$actant % bactericide % detergent % $abric so$tener or conditioner%
hair conditioner 1
6
(d)
H C C
N
O
H
C H
3
3
C H C O O C H N H
3 3 3
)
+
(allow "
!
''" or "
!
''
(
N")
*
) 2
[10]

11. (a) Nucleophilic substitution 1
C H C H C H C H 4 r C H C H C H C H N H
H N
:
:
? 1
? 4
( ) N H
3
3
3
3
2 2 2 2 2 2
H
H
+
? 2 ? 3
4
?1A ?2 and ?4 $or arro(sA ?3 $or structure o$ cation
(Allow M& alone first+ i,e, $N% formation of car-ocation)
(.enalise M) if /r
(
used to remove "
*
)
(b) Step 1 CH
3
CH
2
CH
2
CN 1
CH
3
CH
2
CH
2
4r + 9CN CH
3
CH
2
CH
2
CN + 94r balanced 1
(or CN
)
) (or 4r
)
)
(not "N) 1
Step 2 CH
3
CH
2
CH
2
CN + 2H
2

CH
3
CH
2
CH
2
CH
2
NH
2
1
(or 4:H;)
(c) (i) 5one pair (on N) (in correct conte,t) 1
8 group increases electron densit* % donates electrons %pushes
electrons % has positie inductie e$$ect 1
(ii) 2n* strong acid (but not concentrated)
or an* a"ine salt or a""oniu" salt o$ a strong acid 1
(d) CH
3
CH
2
N(CH
3
)
2
1
[12]
12. (a) (i) chloro"ethaneA an* halogeno"ethane (correct $or"ula accepted) (1)
alu"iniu" chloride % /e % /eCl
3
%4/
3
(1)
anh*drous (1) 3
(ii) electrophilic (1)
substitution (1) 2

7
(b)
C H C l
2
C H C l
2
C C l
3
( 1 ) ( 1 ) ( 1 )
and other correct products 3
penalise C
6
H
5
once onl*
(c) (i) reduction % redo, (1) 1
(ii)
N H C l
3
+ )
2
cation onl*A gie 2
onl* phen*la"ineA gie
salt correct (ith charges o"ittedA gie 2
(d) (i)
O H H
H
C
H
H
C
H
H
C
H
(1)
reduction % redo, % h*drogenation % addition not electrophilic addition (1) 2
(ii)
O H
H C
H
C
H
H
C
H
O
o,idation %redo, (1) 2
(iii)
C N H
H
C
H
O H
C
H
H
C
H
(1)
addition not electrophilic addition (1) 2
[17]
8
13. (a) CHNO
3
+ CH
2
SO
4
(1)
HNO
3
+ 2H
2
SO
4
NO
+
2
(1) + H
3
O
+
+ 2HSO
)
4
(1)
electrophilic substitution (1)
+
N O
2
H
2
N O +
( 1 )
( 1 )
( 1 )
<
(b) reduction or h*drogenation (1)
HC1%/e or Sn or 0n or Sn Cl
2
H
2
%Ni or 1t or 1d or Cu (1) 2
(c) C
6
H
5
NH
2
+ CH
3
COCl (1) C
6
H
5
NHCOCH
3
+ HCl (1)
or C
6
H
5
NH
2
+ (CH
3
CO)
2
O C
6
H
5
NH COCH
3
+ CH
3
COOH
nucleophilic addition7ele"ination (1)
( 1 ) ( 1 ) ( 1 )
( 1 )
C H N H
6 5 2
C H N H
6 5 2
)
C H N H
6 5
C C
C
C l C l
C H
3
C H
3
C H
3
O O
O
+
+
H
<
[16]

14. (a) lone pair on N (1)
donated to H
+
or proton acceptor (1) 2
(b) lone pair on N less aailable (1)
due to delocatisation (1) 2
(c) (i) nucleophilic substitution (1)
(ii) (CH
3
)
2
NH (1)
(CH
3
)
3
N (1)
(CH
3
)
4
N+ 4r
)
(1)
(iii) &uaternar* a""oniu" salt (1) 5
[9]

9
15. (a) (i) CH
3
CN + 4:H; (or 2H
2
) CH
3
CH
2
NH
2
(1)
(ii) 5i2lH
4
or Na%C
2
H
5
OH (or H
2
%Ni) (1) 2
(b) (nucleophilic) substitution or al#*lation (1)
.roduct % .roduct & .roduct !
(C
2
H
5
)
2
NH (C
2
H
5
)
3
N (C
2
H
5
)
4
N
+
4r
)
(1) (1) (1) 4

(c)
@ @
2 2 2 3 3 3
)
+
C H C H N H C H C H N H 4 r
H 4 r
( 1 )
( 1 )
( 1 )
3
(d) lone pair on N less aailable
or electron densit* on N decreased (1)
due to delocalisation (1) 2
(e) electron (ithdra(al b* O or CO
or delocalisation b* CO (1) reduces electron
densit* on N or "a#es N lone pair less aailable (1) 2
($) 2C
2
H
5
NH
2
+ CH
3
COCl (1) CH
3
CONHC
2
H
5
+ C
2
H
5
NH
3
+
Cl
)
(1)
(nucleopholic) addition ) eli"ination (1)
@ @ @ @
2
3 3
5 5
5 3
2 2
2
2
( 1 )
( 1 )
( 1 )
( 1 )
C H N H C O C H N H C O
C H C H
C l C l
C H N H C O C H
H
+
)
+
<
[20]
16. (a) (i) H+ or proton acceptor (1)
CH
3
NH
2
+ H
2
O ( ) CH
3
+
NH
3
(+) OH
)
(1)
(ii) CH
3
NH
3
Cl or HCl (1)
Or any ammonium compound or strong acid
name or formula
(iii) e,tra OH
)
reacts (ith 3 3
+
C H N H
or reaction % e&uilibriu" "oes to le$t
or ratio salt % base re"ains al"ost constant (1)
Any 2
5
(b) lone pair (on N accepts H
+
) (1)
CH
3
increases electron densit* (on N)
10
donates % pushes electrons
has positie inductie e$$ect (1) 2
(c) nucleophilic substitution (1)
C H
N C H C H
C H
3 2
2
2
5
5
5
+
(1) 2
[9]

17. (a) (i) Equation C
6
H
5
CH
2
4r + 2NH
3
C
6
H
5
CH
2
NH
2
+ NH
4
4r (1)
(1)
Type of reaction nucleophilic subsn or al#*lation (1)
Explanation $urther substitution occurs (1)
o gie a "i,ture o$ products (1)
(ii) reduction or h*drogenation (1)
C
6
H
5
CN + 4:H; C
6
H
5
CH
2
NH
2
(1)
or 2H
2
Na%C
2
H
5
OH or 5i2lH
4
or H
2
%Ni (1)
onl* one product $or"ed (1)
or aoids $urther substitution F
(b) 0ea1er base phen*la"ine (1)
Explanation lone pair on N less aailable or electron densit* on
N lo(ered (1)
due to delocalisation or oerlap (1) 3
[12]
18. (a) (i) cHNO
3
+ cH
2
SO
4
(1)
HNO
3
+ 2H
2
SO
4
NO
2
+
(1) + H
3
O
+
+ 2HSO
4
)
(1)
(ii) electrophilic substitution (1)
C O C H C O C H
3 3
N O
N O
2
2
+
: 1 ;
: 1 ;
: 1 ;
: 1 ;
H
+
<
(b) Type of reaction reduction (1) not h*drogenation
Reagent(s) Na4H
4
or Na%C
2
H
5
OH (1) not 5i2lH4
not H
2
%Ni 2
(c) Reagent CH
3
COCl or (CH
3
CO)
2
O (1)
Name of mechanism (nucleophilic addition)eli"ination (1)
Mechanism
11
8 O H C O 8 O C O
C H C H
C H
C l C l
8 O C
O
H
H
+
+
@ @ @ @
: 1 ;
: 1 ;
: 1 ;
: 1 ;
3 3
3
6
(d) Type of reaction reduction or h*drogenation (1)
Reagent(s) HCl%/e or Sn or 0n H
2
%Ni or 1t or 1d (1)
or SnCl
2
or Ni%H
2
not 2iAl"
)
2
(e) optical (1) 1
[18]
19. (a) (i) lone pair on N (1)
(ii) inductie e$$ect o$ CH
3
or electron donation (1)
increases electron densit* on N
or lone pair "ore aailable (1)
(iii) electron densit* on N decreased
or lone pair less aailable (1)
due to delocalisation (1) 5
(b) (i) Equation CH
3
CH
2
CN + 2H
2
CH
3
CH
2
CH
2
NH
2
(1)
atalyst Ni (1)
(ii) nucleophilic substitution (1)
(iii) $urther reaction can occur (1)
bet(een prop*la"ine and 17bro"opropane (1) 5
(c) CH
3
CH
2
CH
2
NHCOCH
3
(1) 1
(d) Type of product &uaternar* a""oniu" salt or chloride (1)
$tructural formula
CH
3
(CH
2
)
11
N
+
(CH
3
)
3
(1)
Cl
)
(1) 3
[14]
20. (a) 5one pair on nitrogen (1) less aailable or
electron densit* lo(ered (1) due to delocalisation or
resonance or "eso"eris" or part o$ , bond (1) 3
(b) Equation C
6
H
11
4r + 2NH
3
C
6
H
11
NH
2
+ NH
4
4r (1)
Name of mechanism nucleophilic substitution (1)
Mechanism
12
N H
. N H
. N H
H
2
3
3
4 r
+
( 1 )
( 1 )
( 1 )
( 1 )
6
(c) (i) NaCN or 9CN (1)
(ii) Reagent(s) Na%C
2
H
5
OH or 5i2lH
4
or H
2
%Ni (1)
Type of reaction reduction or h*drogenation (1)
Equation C
6
H
11
CN + 4:H; C
6
H
11
CH
2
NH
2
(1)
or 2H
2
i$ h*drogenation 4
(d) Equation 28NH
2
+ CH
3
COCl 8NHCOCH
3
(1) + 8NH
3
Cl (1)
Name of mechanism (nucleophilic) addition7eli"ination (1)
Mechanism
2 2
2
3 3
3
( 1 ) ( 1 ) ( 1 )
( 1 )
8 N H 8 N H
8 N H
C C
C
O O
C l C l
C H C H
C H
O
H
.. +
+
<
[20]
21. (a) (i) suitable graphical $or"ula $or ethanoic anh*dride (1) 1
(ii) (acid) anh*dride (1) 1

(b) (i) F = eth*la"ine % a"inoethane (1) 1
(ii) reduction or h*drogenation or addition (ignore re$erence
to "echanis") (1)
1
(c) CH
3
COCl + CH
3
CH
2
NH
2
CH
3
CONHCH
2
CH
3
+ HCl
CH
3
CONHCH
2
CH
3
(1)
balanced (1) 2
[6]
13

22. (a) 5one pair on N or electron densit* on N (1)
"ore aailable or electron densit* increased (1)
electron donation or inductie e$$ect (1) 3
(b) Reagent(s) 5i2lH
4
or Na%6tOH or H
2
%Ni (1)
Type of reaction reduction or h*drogenation (1)
Equation CH
3
CN + 4:H; or 2H
2
CH
3
CH
2
NH
2
(1) 3
(c) (C
2
H
5
)
4
N
+
4r
)
(1)
&uaternar* a""oniu" salt (1)
cationic sur$actant (1)
or $abric so$tener 3

(d) Name of mechanism addition7eli"ination (1)
Mechanism
C H N H C H N H
C H N H
C C
C
H
O O
O
C H C H
C H
C l C l
2 2
2
5 5
5
2 2
3 3
3
.. +
+
( 1 )
( 1 ) ( 1 )
( 1 )
5

(e) C
2
H
5
NH
2
+ (CH
3
CO)
2
O C
2
H
5
NHCOCH
3
+ CH
3
COOH (1)
or 2C
2
H
5
NH
2
+ (CH
3
CO)
2
O C
2
H
5
NHCOCH
3
+ CH
3
COO
)
+
N
H
3
C
2
H
5
1
[15]
14
23. (a) (nucleophilic) additioneli!ination" #
C H C H
C
O
C l
? 2
? 1
a l l o ( C H
3 2
2 5
C H
3
N H
2
( )
( )
C H C H
3 2 C C l
O
N H H C
H
+
)
(M! for structure)
(M) for ! arrows and lone pair)
(M& not allowed independent of M%+ -ut allow M% for correct
attac1
on * if M& show as independent first,)
(*on of 3' loses M& -ut ignore * if correct)
(l
(
removing 4t loses M))
C H C H
3 2
C
N H C H
3
O
5
(5f M$ lost a-ove for wrong chain+ do not penalise same
error again here)
(b) CH
3
CH
2
COCl + 2lCl
3
:CH
3
CH
2
CO;
+
+ 2lCl
4
)
E 1
(penalise wrong al1yl group once at first error)
(position of * on electrophile can -e on ' or or outside 6 7)
(penalise wrong curly arrow in the equation or lone pair on
All
!
)
+
? 2
s t r u c t u r e
? 1
C O C H C H
? 3 a r r o (
H
2 3
C O C H C H
2 3
+
(M% arrow from within hexagon to or to * on )
(don8t penalise position of * on of R'*)
(horseshoe must not extend -eyond
& to 9 -ut can -e smaller)
(* not too close to %)
(penalise M& if "
3
chain wrong
again -ut allow M% and M!)
(M! arrow into hexagon unless
:e1ule)
(allow M! arrow independent of M&
structure)
3
HClE 2lCl H 2lCl
3
)
4
+ +
+
1
(or can -e gained in mechanism);

15
(c) $# CH3CH2COCl + H2O % CH3CH2COOH + HCl # #
(penalise wrong alkyl group once at first error)
?2 ?r o$ CH3CH2COCl + F2@5 1 1
(if Mr wrong+ penalise M& only)
?3 "oles o$ CH3CH2COCl + 1@43%F2@5 + !@!16 1 1
?4 "oles NaOH + 2 G !@!16 + !@!32 1 1
(allow for G & conseq to wrong no of moles)
?5 olu"e o$ NaOH + !@!32%!@42 + !@!<62 d"3 or <6@2 c"3 1
(with correct units)
(if G& missed in M) lose M< also) 1
[16]

24. (a) CH
3
COCl + 2lCl
3
CH
3
+
C
O + 2lCl
4

1
e&uation 1
penalise (rong al#*l group once at $irst error
position o$ + on electrophile can be on O or C or outside : ;
penalise (rong curl* arro( in the e&uation or lone pair on 2lCl
3
else ignore
6lectrophilicHsubstitution 1
N'T 4= acylation
O
C C H
3
? 1
+
? 3
? 2
H
C O C H
3
horseshoe must not extend -eyond & to 9 -ut can -e smaller
* not too close to %
M! arrow into hexagon unless :e1ule
allow M! arrow independent of M& structure
?1 arro( $ro" (ithin he,agon to C or to + on C
+ "ust be on C o$
8CO
3
16
(&) Nucleophilic'addition NO( reduction #
? 1
? 2
O C
C H 3
H
)
O C H
C H
H
)
+
? 4
? 3
3
4
M& not allowed independent+ -ut can allow M% for attac1 of "
(

on * formed
1)phen*lethan()1))ol or (1)h*dro,*eth*l)ben=ene 1

(c) deh*dration or eli"ination 1
(conc) H
2
SO
4
or (conc) H
3
1O
4
1
allow dilute and Al
&
'
!

>o not allow iron oxides
[14]
25. (a) eth*l ben=ene 1
chloroethane or bro"oethane (or ethene and hydrogen chloride=-romide) 1
alu"iniu" chloride%bro"ide or iron(>>>) chloride %bro"ide or iron +
chorine%bro"ine 1
CH
3
CH
2
Cl + 2lCl
3
I CH
3
CH
2
+
+ 2lCl
4
)
1
electrophilic substitution 1
+
C H C H H
? 1
? 2
s t r u c t u r e
? 3 a r r o (
2 3
C H C H
2 3
+
3
(b) 1
C
O
C H C H
2 3
CH
3
CH
2
COCl % propano*l chloride or (CH
3
CH
2
CO)
2
O % propanoic anh*dride 1
Na4H
4
or 5i2lH
4
or H
2
%Ni (not $n=4e with "l) 1
[11]
17
26. X i) CH
3
CN or ethanenitrile or ethanonitrile or !eth*l c*anide or #
c*ano!ethane or eth*l nitrile or !ethanecar&onitrile
Not ethanitrile
-ut contradiciton of name and structure lose mar1s
Y is CH
3
CH
2
NH
2
or eth*la"ine or a"inoethane or ethana"ine 1
Step 1. reagent 9CN not HCN%HCl 1
condition (a&)%alcohol 7 onl* allo( condition i$ reagent
correct or inco"plete 1
Step 2. reagent H
2
5i2lH
4
Na 0n%/e%Sn Not Na4H
4
1
condition Ni%1t%1d ether ethanol HCl 1

Z is an a"ine or a"inoal#ane or na"ed a"ine een i$ incorrect na"e $or Z 1
secondar* (onl* a(ard i$ a"ine correct)
C H C H N C H
C H
3 3 2
3
3
C H
+
(4r
)
) + can be on N or outside brac#ets as sho(n 1
nucleophilic substitution 1
[9]
27. (a) C*clohe,ane eoles 12! #J "ol
)1
(e,pect triene to eole) 36! #J "ol
)1
(1) or 3 G 12!
36! ) 2!3 + 152 #J (1) NOK 15! 4
%<& can score first &
?of2@ -enAene lower in energy = more (stated) sta-le (1)
Not award if mentions energy required for -ond
-rea1ing
due to delocalisation (1) or explained
18
(&) (i) phen*la!ine +ea,er (1)
if wrong no mar1s
lone pair on N (less aailable) (1)
delocalised into ring (1) or Be,plainedC 3
(ii) addition ) eli"ination (1)
( C H ) N H
? 1
( C H ) C C
O
O
C l
C l
? 2
( 1 )
( 1 )
C H N H
H
3
6
6
5
5
3
2
@ @
@ @
C H
+
structure (1) M!
! arrows (1) M)
N7phen*l ethana"ide (1) 6
(iii) conc HNO
3
(1)
conc H
2
SO
4
(1)
HNO
3
+ 2H
2
SO
4

+
N
O
2
+ H
3
O
+
+ 2HSO
4
)
(1)
N O
N O
2
2
+
+
H
? 3
? 1
? 2
( 1 )
( 1 )
( 1 )
6
(i) peptide % a"ide (1)
NaOH (a&) (1) 2
"l conc or dil or neither
"
&
$'
)
dil N'T conc
N'T Bust "
&
'
19
Notes
(a) 36! or 3 G 12! or in (ords (1)E
152 NOK 15! (1)E (152 can get $irst t(o "ar#s)
Q of L ben=ene "ore stable but not a(ard i$ H alues used to sa*
that "ore energ* is re&uired b* ben=ene $or h*drogenation co"pared (ith
the triene or i$ ben=ene is onl* co"pared (ith c*clohe,ene (1)E
delocalisation or e,plained (1)
(b) (ii) or N7phen*laceta"ide or acetanilide
"echanis". i$ sho(n as substitution can onl* gain ?1
i$ CH
3
CO+ $or"ed can onl* gain ?1
lose ?4 i$ Cl
)
re"oes H
+
be lenient (ith structures $or ?1 and ?2 but "ust be correct $or ?3
C O alone loses ?2
(iii) No mars for name of me!"an#sm #n t"#s $art
i$ conc "issing can score one $or both acids (or in e&uation)
allo( t(o e&uations
allo( HNO
3
+ H
2
SO
4
NO
2+
+ HSO
4
)
+ H
2
O
ignore side chain in "echanis" een i$ (rong
arro( $or ?1 "ust co"e $ro" niside he,agon
arro( to NO
2
+
"ust go to N but be lenient oer position o$ +
+ "ust not be too near BtetrahedralC Carbon
horseshoe $ro" carbons 276 but donDt be too harsh
(i) reagent allo( NaOH
HCl conc or dil or neither
H
2
SO
4
dil or neither but not conc
not -ust H
2
O
[21]
20