Q1.

A possible synthesis of 1,4-diaminobenzene is shown below.

(a) Identify a suitable reagent or combination of reagents for Step 1. Name and outline
a mechanism for the reaction.
(6)

(b) Identify a suitable reagent or combination of reagents for Step 2. Name and outline
a mechanism for the reaction.
(6)

(c) Identify a suitable reagent or combination of reagents for Step 4. Draw the repeating
unit of the polymer formed by reaction of 1,4-diaminobenzene with pentanedioic
acid.
(3)
(Total 15 marks)

Q2.
(a) Compound C, H2N(CH2)4NH2, can be synthesised from ethene in three steps as
shown below.

Step 1 Step 2 Step 3

Ethene Compound Compound Compound
addition A substitution B C
reaction reaction C 4 H4 N2 H2N(CH2)4NH2

Name compound C and draw a structure for each of compounds A and B.

State the reagent(s) required for each step and name the type of reaction involved in
the conversion of B into C.
(7)

(b) Draw the repeating unit of the polyamide formed when C reacts with hexanedioic
acid. Discuss the interactions between the chains of the polyamide.
(4)

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 (c) Explain why polyamides are degraded by sodium hydroxide whereas polymers such
as poly(ethene) are not.
(3)
(Total 14 marks)

Q3.
Refer to the following reaction sequence:

Which one of the following would be the most appropriate to carry out Step 2?

A H2 / Ni

B Sn / HCl

C NaBH4

D Fe / HCl
(Total 1 mark)

Q4.
Which one of the following types of reaction mechanism is not involved in the above
sequence?

CH3CH2CH3 (CH3)2CHCl (CH3)2CHCN

(CH3)2CHCH2NHCOCH3 (CH3)2CHCH2NH2

A free-radical substitution

B nucleophilic substitution

C elimination

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 D nucleophilic addition-elimination
(Total 1 mark)

Q5.
Use the data given on the back of the Periodic Table (PT) to help you answer this
question.
Compounds A to G are all isomers with the molecular formula C6H12O2

(a) Isomer A, C6H12O2, is a neutral compound and is formed by the reaction between
compounds X and Y in the presence of a small amount of concentrated sulphuric
acid.
X and Y can both be formed from propanal by different redox reactions.
X has an absorption in its infra-red spectrum at 1750 cm–1.
Deduce the structural formulae of A, X and Y. Give suitable reagents, in each case,
for the formation of X and Y from propanal and state the role of concentrated
sulphuric acid in the formation of A.
(7)

(b) Isomers B, C, D and E all react with aqueous sodium carbonate to produce carbon
dioxide.
Deduce the structural formulae of the three isomers that contain an asymmetric
carbon atom.
The fourth isomer has only three singlet peaks in its proton n.m.r. spectrum. Deduce
the structural formula of this isomer and label it E.
(4)

(c) Isomer F, C6H12O2, has the structural formula shown below, on which some of the
protons have been labelled.

A proton n.m.r. spectrum is obtained for F. Using Table 1 at the back of the Periodic
Table (PT), predict a value of δ for the protons labelled a and also for those labelled
b. State and account for the splitting patterns of the peaks assigned to the protons a
and b.
(6)

(d) Isomer G, C6H12O2, contains six carbon atoms in a ring. It has an absorption in its
infra-red spectrum at 3270 cm–1 and shows only three different proton environments
in its proton n.m.r. spectrum. Deduce a structural formula for G.
(2)
(Total 19 marks)

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Mark schemes

Q1.
(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)

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)

M2 structure
M3 arrow
6

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

NOT LiAlH4 NaBH4

3
[15]

Q2.
(a) 1, 4-diaminobutane or butane -1, 4-diamine (1)
A: BrCH2CH2Br or ClCH2CH2Cl (1)

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 B: NC CH2CH2CN
Step 1: Br2 or Cl2 (1) (ignore aq)
Step 2: KCN (1) (NOT HCN)
Step 3: H2 / Ni or LiAlH4 or Na / C2H5OH (1) (NOT NaBH4)
Hydrogenation only for H2 / Ni, or nucleophilic addition only for LiAlH4(1)
OR reduction or addition
7

(b)

QL hydrogen bonding (1)

Polarity of H-bonding shown or discussed (1)

4

(c) Polyamides / peptide link can be hydrolysed (1)

OR polyalkenes cannot be hydrolysed

QL OH– attacks peptide link or C + (1)



poly(ethene) non-polar (1)

3
[14]

Q3.
C
[1]

Q4.
C
[1]

Q5.
(a) X contains > C=O (1)
if X and Y reversed lose this mark but allow remaining max
6/7

X is CH3CH2COOH (1)

Y is CH3CH2CH2OH (1)

A is (1)

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 Conc H2SO4 : catalyst (1)
7

(b)

(c) 3.1 – 3.9 (1)

2.1 – 2.6 (1)

a: quartet (1) 3 adjacent H (1)

b: triplet (1) 2 adjacent H (1)

6

(d) 3269 cm–1 OH alcohol (1)

G is (1)
2

Notes

(a) first mark for C=O stated or shown in X

Ignore wrong names

Y CH3CH2CH2OH
allow C3H7 in A if Y correct or vice versa
Allow (1) for A if correct conseq to wrong X and Y

other oxidising agents: acidified KMnO4; Tollens; Fehlings

other reducing agents: LiAlH4; Na/ethanol; Ni/H2; Zn or Sn or Fe/HCl

(b) give (1) for carboxylic acid stated or COOH shown in each suggestion
(1) for correct E
any 2 out of 3 for B, C or D
allow C3H7 for either the B or D shown on the mark scheme
i.e. a correct structure labelled B, C or D or E will gain 2.

(c) protons a – quartet must be correct to score 3 adjacent H mark. Same for b

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(d) allow (1) for any OH (alcohol) shown correctly in any structure – ignore extra
functional groups. Structure must be completely correct to gain second mark
[19]

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–

Page 7 of 7