4.8, 4.

9 EXAM QUESTIONS MS
1. (a) Equation CH3COCl + CH3CH2OH → CH3COOCH2CH3 + HCl (1)
Name of mechanism addition-elimination (1)
Mechanism
(1) (1) Cl (1)
Cl
+
:

:
–
CH 3 CH 2 O C O CH 3 CH 2 O C O
CH 3
H H CH 3

+ O
CH 3 CH 2 O C
CH 3
(1) H 6
(b) Only the polyester (1) is hydrolysed (1) by alkali 2
[8]

2. (a) elimination (1) 1

(b) melting point increases (1)
boiling point increases(1)
or they are liquids, the higher members are solids(1)
density increases(1)
viscosity increases(1) max 2
(c) addition (1)
polymerisation (1) 2
(d) (i) C2H4 + H2O→ C2H5OH - must show the functional group (1) 1
(ii) vapour phase / high temperature (300 ± 50°C) (1)
high pressure 70cl ± 20 (1)
if high T and high p, then only 1 mark, value for either gives 2nd mark
strong acidic catalyst /H3PO4 (1) 3
(iii) electrophilic (1)
addition (1) 2
[11]

1
3. (a) nucleophilic addition; 1
C 2 H 5 or
H H
M2 M4
(CH 3 CH2 ) C CH 3 CH2 C –
O O
NC H+
–
NC M1
M3 structure ; 4
(be lenient on position of charge on CN– )
(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 δ+ if correct)
(M4 for arrow and lone pair (only allow for correct M3 or
close))
(b) (i) 2-hydroxybutanoic acid 1
(ii)
H 3C H
C C
H COOH

H 3C COOH
C C
H H
1
1
geometric(al) or cis-trans 1
(c) (i)
CH 3
(O C CH2 C )
H O
1
(one unit only) (ignore brackets or n) (trailing bonds are needed)
(ii) can be hydrolysed
OR
can be reacted with/attacked by acid/base/nucleophiles/H2O/OH–; 1

2
 (d) (i)
+
NH 3
CH 3 CH 2 C H
COO – 1
(allow –NH3+)

(ii)
NHCH3
CH 3 CH 2 C H
COOH 1
(or zwitterions product)
(iii) nucleophilic substitution; 1
[14]

4. (a) (i)
CH 3
+ –
H3 N C COO
H
penalise +NH3— or + on H once per paper 1
zwitterions 1
(ii)
CH 3
+
H3 N C COOH
H 1
(b)
CH 3
N C C
H H O
ignore n, but allow one drawn out repeating unit only 1
condensation or (nucleophilic) addition-elimination 1
(c) 3-methylpent-2-ene 1
[6]

5. (a) (i) H H 1

C C

H CN
(Ignore n or brackets, but trailing bonds are essential)
(ii) Addition or radical 1

3
 (b) (i) 2-aminobutanoic (acid) 1
(ii) CH 2 CH 3 1
+
H3N C COOH

H
(c) (i) C3H4O2 1
(ii) HO C CH 2 CH2 C OH 1

O O
(1,4-)butan(e)dioic (acid) 1
(allow succinic, but not dibutanoic nor butanedicarboxylic acid)
(iii) Can be hydrolysed / can react with acid or base or water / 1
can react with nucleophiles
[8]

6. (a) (i) 2-methylbut-1-ene (1)

NOT ...butan....
CH 3 CH 2
(1)
(ii) Repeating unit: ( )C CH 2 ( ) or 2 ×

CH 3
allow C2H5

Type of polymerisation: addition or radical (1)

(iii) Name of mechanism: electrophilic substitution (1)
CH 3
Major product: C CH 2 CH 3 (1)

CH 3
(iv) CH3CH=CHCH2CH3 (1) 6
(b) Repeating unit:
O O H H
( )C CH2 CH2 C N (CH2)6 N( )
CONH
(1) (1)
Type of polymerisation: condensation (1)
Name of linkage: (poly)peptide or (poly)amide (1) 4
allow outer horizontal bonds to be omitted
allow HO–[...........]–H if [......] shows the repeating unit; if
brackets missing in the dimer, penalise one
C2H4 or C6H12 first time only
allow CONH
allow polypeptide or polyamide; peptide or amide must be
spelled correctly

4
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.
R H R H
H 3 N: C Br OR H 3 N: C Br

H H
(2) Structures

penalise sticks (i.e. C ) once per paper

H H
HO C R or R C OH or –NH 3
H H
H H
OH C R or R C HO H 2 N–
H H etc

Penalise once per paper

allow CH3– or –CH3 or CH 3 or CH3

or H3C–
[10]

7. (a) (i) O O (1) 1

C C
HO OH
(ii) H H allow HOCH2CH2OH (1) 1
H O C C O H

H H

O O
H H
C C
(iii)
O O C C

H H
n
ester linkage correct ie –COO–CH2– shown as fully graphical structure (1)

rest of molecule correct including n

(1)
repeat unit may start and finish in different place
allow e.c.f. from (a)(ii) 2

(b) polyesters (1) 1

5
 (c) addition: joining together (of monomers with double bond) →
one product only (1)
condensation: also involves the elimination of a small molecule (1)
allow specific example e.g. H2O, HCl, CH3OH 2
(d) poly(ethene) / poly(propene)
condone missing brackets (1) 1
[8]

8. (a) Substance 1: HCl or HBr (1)

Substance 2: AlCl3 / AlBr3 / FeCl3 / FeBr3 (1) 2

(b) H2C==CH2 + HCl +AlCl3 → CH3CH2+ + AlCl4– (1)

Allow 2 equations 1

(c) Name of mechanism: electrophilic substitution (1)

Mechanism: (1) 4
+ H
CH 2 CH 3
+
CH 2 CH 3
(1) (1)
(d) 1
(1)

(e) Type of polymerisation: addition (1)

Repeating unit: CH CH (1) 2
2

[10]

9. (a) (i) hexane-1,6-diamine or 1,6-diaminohexane (allow ammine)

or 1,6 hexan(e)diamine (1)
(ii) ( )C (CH 2 )4 C N (CH 2)6 N ( )
(1)
O O H H
Allow –CONH–

6
 (b) (i) CH 3
H 2N C COOH (1)
H
CH 3 CH 3
H 2N C C N C COOH (1)
H O H H

peptide link essential : the rest is consequential on b(i)

(allow CONH)
(ii) 2
allow anhydride
CH 3 CH C O C CH CH 3
NH 2 O O NH 2

(c) (i) quaternary ammonium bromide salt (1)

(not ion, not compound)
Allow quarternery

(ii) Reagent: CH3Br or bromomethane (1)

penalise CH3Cl but allow excess for any halomethane

Condition: excess (CH3Br) (1)

(iii) nucleophilic substitution (1) 4
[8]

10. (a) electrophilic addition (1)

+ (1)
H 2C CH 2 H 2C CH 2

(1) Cl Cl
(1) –
:

(1) Cl
Cl 5
(b) CH 2 CH 2 H H 1
C 2 H 4 Cl 2 or C C + HCl
Cl Cl H Cl
(1)
(c) ester or alkoxy alcohol (1) 1
(d) (i) HO–CH2–CH2–OH (1)
(ii) high electron density of double bond (1)
repels OH– or nucleophile (1) 3
[10]

7
11. (a) (i) the joining together of monomers / small molecules (1)
to form long chains / large molecules (1) 2
(ii) nCH2 = CH2 → (-CH2–CH2-)n (1)
allow n CH2 CH2 not n C2H4 1
(b) 1,2-dibromoethane (1) 1
(c) electrophilic addition (1)
H H H H H H

C C H C C H H C C H
H H Br :Br – Br Br
δ+
Br

δ–
Br
words or diagrams to show attack by p electrons on Br atom
and either δ+/δ– on Br2 or e– shift on Br–Br (1)
correct carbocation intermediate (allow triangular representation) (1)
attack by Br– (onto +ve carbon) leading to correct product (1) 4
(d) (i) C 38.71/12 = 3.23 ; H 9.68/1 = 9.68 ; O 51.61/16 = 3.23 (1)
ratio C:H:O = 1:3:1 /empirical formula = CH3O (1)
empirical mass = 31 so molecular formula = 2 × CH3O = C2H6O2 (1) 3
(ii) reagent = NaOH / KOH (1)
conditions = aqueous solution (dependent on first mark) (1) 2

(iii) CH2BrCH2Br + 2NaOH → CH2(OH)CH2OH + 2NaBr

product = CH2(OH)CH2OH (condone missing brackets) (1)
correctly balanced (1) 2
if C2H6O2 given, allow second mark only
for CH2 Br CH2 Br + 2H2O → CH2(OH)CH2(OH) + 2HBr
allow 2 marks if reagent in (ii) is H2O or aqueous solution
[15]

8
12. (a) CH3COCl or (CH3CO)2O (1)
AlCl3 or H2O or CH2SO4 loses this mark
CH3COOH loses reagent and M3, M4 = max 3

nucleophilic addition–elimination (1)

M1 (CH ) H CH 3
3
+

:
(Ph)NH 3 C O N C O –

Cl
M2 H Cl
M3: structure
M4: 3 correct arrows
+
Allow M1 for attack on CH3-C =O
– +
Penalise Cl removing H

6
(b) Conc HNO3 (1)
Conc H2SO4 (1)
HNO3 + 2 H2SO4 → NO2+ + H3O+ + 2 HSO4– (2)
(or H2SO4 ) (or H2O + HSO4–)
HNO3 / H2SO4 scores 1
Any 2

electrophilic substitution (1)

NHCOCH 3 NHCOCH 3

+
M1

+NO 2 H NO 2
M2 structure
M3 arrow

(c) Sn (or Fe) / HCl or Ni / H2 (1)

NOT LiAlH4 NaBH4

O O H H
C (CH 2 )3 C N N

(1) (1) 3
[15]