Winter 2000 CH4 Mark Scheme

1.

(a)

(b)

C
69.8 / 12
H
11.6 / 1
O
18.6 / 16
EF is C5H10O(1)
(i)

(ii)
(iii)

=
=
=
2

5.8
11.6
1.16

/ 1.16
/ 1.16
/ 1.16

5
10
1

amount NaOH = 0.0374dm3 0.211moldm3 (1)

= 7.89 103 mol
amount of W = 7.89 103 mol(1)
Mr = 1.36 g = 172 (gmol1)(1)
7.89103 mol
Note: can get 3 marks for correct calculation which
assumes second mark.

Emp formula mass = 86 thus MF is Cl0H20O2(1)

(some reasoning needed for this mark)

C9H19COOC2H5 + NaOH C9H19COONa + C2H5OH (2)

correct ester formula (1) balanced equation (1)
or ionic equation
Note: max (1) if added up formulae used or wrong ester formula
or RCOOC2H5

[8]

2.

(a)

Correct arrows involving C=C and HBr(1)

Correct intermediate with positive charge(1)
Correct arrow from Br towards carbon atom (1)

CH 3

CH 3

CH 3 CHBrCH 3

H
H

:Br

Br

Note: if product is 1-bromo product max 2 for full correct mechanism.

(b)

(i)

Reagent: magnesium(1)
dry ethoxyethane / ether(1)

iodine catalyst / warm under reflux (or at room temperature)(1)

(ii)
(c)

Reagent: aqueous or dilute sodium hydroxide(1)

Conditions: boil / heat under reflux(1)

Reagent: carbon dioxide (solid)(1)

Reagent second stage: water or dilute named acid (1)
Note: a route using methanal followed by oxidation can score (2) marks
CH 3

(d)
CH 3
CH 3

C
O

2
2

CH 3

(2)

Note: if one branched and one straight chain on correct ester linkage (1)
[12]

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Winter 2000 CH4 Mark Scheme

3.

(a)

O
n

(b)

(c)

(d)

Correct structure if linkage (1)

Some evidence of continuation of molecule (1)

Peak at A : C=O (1)

Peak at B : C O (1)
Spectrum is that of benzene 1,4- dicarboxylic acid (1)

(i)

To prevent the volatile reactant / dimethyl benzene boiling off (1)

(ii)

Because the diacid is soluble in hot water (1)

(iii)

M.Pt not sharp

or different from / not consistent with / less than data book (1)
or
F H F H
F H H F

(i)

(or H...F...F...H on chain)

Correct repeating structure (1)
Some evidence of continuation of molecule (1)
(ii)
(e)

(i)
(ii)

Kevlar : condensation(1)
PDFE : addition (1)

more carbon dioxide per kJ of energy (1)

therefore more global warming/ more greenhouse gas produced (1)

Some reference to need for special arrangements for filling tank /

dangerous in the event of a crash /more weight as gas tank
weighs more than petrol tank / more likely to leak because gas
under pressure (1)

1
[15]

CH 3

CHCl

CH 2 OH

CH 3

4.

(a)

(i)
CH 3

CH(OH)

CHCl COOH

41=4

COOH

COO Na

COOH
D

B consequential on A
C consequential on B
(ii)

2-chloropropan-1-ol (mark consequentially)

et

Winter 2000 CH4 Mark Scheme

(b)

C 2 H 5 COCl

NH 3

C 2 H 5 CONH 2
(1)

(1)

P2 O 5

(1)

C 2 H 5 CN
(1)

Na/C 2H 5OH
or LiAlH 4

C 2 H 5 CH 2NH 2

(1)

or

(1)
C 2 H 5 COCl

H 2O

C 2 H 5 COOH

LiAlH 4

C 2 H 5 CH 2 OH
(1)

KBr/concH 2SO 4

(1)

C 2 H 5 CH 2 Br
(1)
NH 3 (1)

C 2 H 5 CH 2 NH 2
5
(c)

(i)

NH 2 + NaNO 2 + 2HCl

NCl + 2H 2 O + NaCl

1 for diazo cation + (1) for rest of equation

(ii)

if greater than 5C X decomposes (1)

if less than 0C rate (of formation of X) is too slow (1)

OH
(iii)

(1) for N=N link

(1) for link to correct ring
next to OH

[16]

et