Della

04/03/22

15

5 Acetaminophen, CxHyNO2 and phenacetin, C10H13NO2 are two most common and widely
used analgesic in phamaceutical industry.

(a) Some information about acetaminophen is given.

3 ishown.

(3)

(1)

(2) (2)

(1)

chemical shift / ppm

The high resolution mass spectrum of acetaminophen has a peak due to the
molecular ion at m/e = 151 and a peak at m/e = 152 with an abundance of
8.8% of the 151 peak.
The low resolution mass spectrum of acetaminophen has major peaks at
m/z = 43 and m/z = 108.
Acetaminophen contains one fuctional group similar to protein.
Acetaminophen reacts with Group 1 metals and sodium hydroxide but not with
sodium carbonate.

Use this information to answer (i) (v).

(i) Determine the no. of carbon atoms, x, in acetaminophen and state its
molecular formula. Show your working.

[1]
 16

(ii) Suggest structure for acetaminophen showing all the hydrogen atoms.

HO - -

Y
- I
11

-
CH ,

[1]
C =
8 1-1=9 0=2
,
,
, N =L (iii) Suggest the molecular formula of the fragment of acetaminophen at
(8×12) 1-91-(2×16) 1-14=151 m/z = 108.
151
......................................................................................................................[1]

(iv) On the structure you drawn in (ii), circle and label the protons responsible for
the 1 in acetaminophen.
[1]

(v) NMR analysis of acetaminophen is repeated using heavy water as the solvent.
Only three peaks appear in the new spectrum.

Explain why and include an equation.

The NH and 01-1 Peak does not appear its proton exchanged with that of 1720
..........................................................................................................................
.

..........................................................................................................................

......................................................................................................................[2]

(b) NMR spectrum of phenacetin has two more peaks compared to the spectrum of
acetaminophen. The type of proton responsible for H and they are
next to each other.

Complete the following table:

structures Chemical shift splitting pattern

CH2 O 3. 2 -4 PPM quartet

CH3 0.9 -
1. 7- PPM triplet

[2]
 17

(c) Acetaminophen and phenacetin are polar compounds. The mixture of these two can
be separated using gas-liquid chromatography, GLC.

State and explain which one will have longer retention time, Rt when analysed using
GLC.
Phenacetin is more Polat therefore slower reaction time
......................................................................................................................................
.

......................................................................................................................................

..................................................................................................................................[2]

[Total: 10]

6 Yellow dye is a very important basic colour in industry. It can be obtained naturally from plant
or via synthetic synthesis in the laboratory.

(a) The natural yellow dye can be obtained from curcumin. The structure of curcumin is
shown below.

(i) State three functional groups present in curcumin.

one dike tone moiety and two Phenolic groups
......................................................................................................................[1]

(ii) Curcumin reacts separately with the two reagents shown in the table.

Complete the table by:

drawing the structure of the organic or suitable inorganic products
formed
stating the types of reaction.
 18

reagent organic or inorganic product structure type of reaction

hot /
Ho
11° OH 11° OH
Oxidation
concentrated to
KMnO4 / H+ ' ¥ y
Ho

tctlz

Bt
o OH Bi

%É
'
electrophilic
an excess of Dt
addition
Bt Bt
Br2(aq)
HO '
OH
tctlz Hsct

[6]

(b) Methyl orange is the example of synthetic yellow dye which is useful as an indicator
in the determination of end point of acid-base titration. Given below is its structure.

(i) On the structure of methyl orange, circle th

the yellow colour of the dye.
[1]
 19

(ii) When acid is added to methyl orange solution, the hydrogen ion, H+ combined
with this indicator hence it changes from yellow to red colour.
+
Suggest the structure of methly or complex which give rise to the red
colour.

Hzc
Ht
N N N
503 Nat
-
-

Hzc

[1]

(c) Methyl orange can be synthesised as shown.

O2N SO3 Na+

step 1 step 2

O2N H2N SO3 Na+

step 2 step 3

H2N

step 4 at
NH
503 Nat
-

H3C
N +
H3C Y
 20

(i) Deduce the identity of commpound Y and draw the structure in the box. [1]

(ii) Draw the mechanism showing the reaction of bezene in step 1. Include all
relevant species, arrows, and charges.

H
Noz 402
7
~ Ht
①
→ > +
NO,
-

[2]

(iii) Suggest reagents and conditions for step 2, step 3 and step 4.
HCI.sn
step 2 ................................................................................................................
HCl
step 3 ................................................................................................................
aqueous methane
step 4 ................................................................................................................
[3]

[Total: 15]
 21

7 The structure of two polymers A and B are shown.

(a) Polymer A is known as Kevlar® which known to be very strong, but flexible. Its long
linear polymer chains can line up next to each other in a regular pattern.

(i) Name one intermolecular force in polymer A which result in the exceptional
properties of Kevlar®.
hydrogen bonds
......................................................................................................................[1]

(ii) Draw a diagram to show how the intermolecular force in (i) hold the polymer
chains in Kevlar®. Include at least two parts of structure A with one repeat unit
in your diagram.

if
-

i
-
o - n -

.
H

% ,

§
i

-1 :
-
c - N
i
H
-

[1]
 22

(b) Polymer B is known as neoprene formed by the polymerisation of

2-chlorobuta-1,3-diene, CH2 CH=CH2.

2-chlorobuta-1,3-diene can also be used to make a synthetic rubber copolymer,

known as SBR, by 1:1 polymerisation with phenylethene (styerene), C6H5CH=CH2.

(i) Define what is copolymer?

A polymer formed when two more different types of monomer are linked
..........................................................................................................................
or

in the same polymer chain

..........................................................................................................................
.

......................................................................................................................[1]

(ii) Draw part of the structure of SBR, showing one repeat unit.

CH , CC IC H2 Cl-12 - -
CH , C Hz -

[1]

[Total: 4]