PRE-UNIVERSITY & GENERAL STUDIES GAPP 2020

GMI GERMAN UNIVERSITY PREPARATORY PROGRAM MARK SCHEME

GMI-PGS CHEMISTRY TEAM :

NAME : TTO : MS CYNTHIA DATE :
AS ORGANIC TUTORIAL 2

1. Propane, C3H8, is used in the reaction sequence shown below.

A B
H3C—CH2—CH3 Reaction 1 H3C—CH2—CH2—Cl Reaction 2 H C—CH —CH
3 2 2—OH
Cl2 / uv light OH—(aq)/heat

Reaction 3 ethanolic OH—/heat

OH
│
E H3C—CH=CH2 H3C—CH—CH3
polymerisation C Reaction 4 D

(a) The reaction sequence shows several important reaction mechanisms. Select from reactions 1 to 4, the
reaction that shows
(i) free radical substitution, reaction 1
(ii) electrophilic addition, reaction 4
(iii) elimination reaction 3

(b) In reaction 2, the aqueous OH– acts as a nucleophile.

(i) State what is meant by the term nucleophile. Lone pair donor

(ii) With the aid of curly arrows, draw the mechanism involved in reaction 2. Show any relevant dipoles.

CH3CH2 CH2CH3 CH2CH3

(c) Compounds B and D are structural isomers of each other.

(i) State what is meant by the term structural isomers.
Compounds with the same molecular formula but different structural formula.

(ii) Draw the skeletal formulae of compounds B and D.

OH

OH

B D
(d) Compound C can be polymerised to form compound E. Draw a section of compound E. Show two repeat
units.
A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL

2. Compound E contains two functional groups, one of which is a primary alcohol.

(a) Name the other functional group and state how you could test for it.
Alkene. Bromine water decolourises.

(b) Name compound E. 3-methylhex-2-en-1-ol

(c) Compound E can be oxidised to form a carboxylic acid.

(i) State a suitable oxidising mixture for this reaction.
K2Cr2O7 and H2SO4

(ii) Write a balanced equation for this oxidation of compound E. Use [O] to represent the oxidising
mixture.
CH3CH2CH2C(CH3)=CHCH2OH + 2[O] → CH3CH2CH2C(CH3)=CHCOOH + H2O

(iii) Explain how compound E and the carboxylic acid could be distinguished by infra-red spectroscopy.
Carboxylic acid will have absorptions between 1680 – 1730 cm-1 and between 2500 – 3000 cm-1
whereas compound E will not have these absorptions.

(d) Compound E reacts with an excess of HBr to produce a mixture of two organic compounds, each with the
molecular formula C7H14Br2. Identify both organic compounds in the mixture.

3. Both acrolein, CH2=CHCHO, and acrylic acid, CH2=CHCOOH, can be made from prop-2-en-1-ol,
CH2=CHCH2OH.

(a) Name the functional group common to both prop-2-en-1-ol and acrolein. Alkene

(b) Prop-2-en-1-ol can be oxidised to form either acrolein or acrylic acid. Identify a suitable oxidising
mixture. Write a balanced equation for the oxidation of prop-2-en-1-ol into acrolein. Use [O] to represent
the oxidising agent.

Copyright of German Malaysian Institute. All rights reserved. 2

A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL

K2Cr2O7 and H2SO4

CH2=CHCH2OH + [O] → CH2=CHCHO + H2O

(c) A sample of prop-2-en-1-ol was oxidised and an infra-red spectrum of the organic product was obtained.
By referring to your Data Booklet, decide whether acrolein, CH2=CHCHO, or acrylic acid, CH2=CHCOOH,
was formed. Explain your answer.

Acrylic acid.
Absorption approx. 1700 cm-1 indicates C=O
Absorption approx. 3000 cm-1 indicates O-H

(d) Acrylic acid reacts with prop-2-en-1-ol to produce an ester.

(i) Write the balanced equation for this reaction.
CH2=CHCOOH + CH2=CHCH2OH → CH2=CHCOOCH2CH=CH2 + H2O

(ii) Draw the structure of the ester. Clearly display all of the functional groups.

OR

4. 1-Bromo-2-methylpropane is used in the production of ibuprofen and can be prepared from the reaction
between 2-methylpropan-1-ol and HBr.
(CH3)2CHCH2OH + HBr → (CH3)2CHCH2Br + H2O
(a) A student reacted 4.44 g of 2-methylpropan-1-ol with an excess of HBr. The student produced 5.48 g of
1-bromo-2-methylpropane.
(i) Calculate the number of moles of (CH3)2CHCH2OH used.
No of moles = 4.44/74 = 0.0600 moles

(ii) Calculate the number of moles of (CH3)2CHCH2Br collected. 5.48/137 = 0.0400 moles

Copyright of German Malaysian Institute. All rights reserved. 3

A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL

(iii) Calculate the percentage yield. Give your answer to three significant figures.
0.04/0.06 x 100% = 66.7%

(b) Chloroethene, CH2CHCl, is polymerised to form poly(chloroethene) commonly known as pvc.

(i) Draw a section of pvc showing three repeat units. Put a bracket round one repeat unit.

(ii) Polymers such as pvc are difficult to dispose of because they are non-biodegradable. Increasingly,
they are disposed of by combustion. State the problem associated with the combustion of polymers
such as pvc.
Harmful or toxic fumes are produced.

(iii) State two ways in which chemists are trying to minimise the damage to the environment caused by
the disposal of halogenated plastics such as pvc.
Recycle, crack polymers, use as feedstock

(c) Bromochlorodifluoromethane has been used as a flame retardant. When exposed to high temperatures,
one of the C–halogen bonds undergoes homolytic fission to produce free radicals. Suggest, with a reason,
which C–halogen bond is most likely to be broken.
The C – halogen bond most likely to be broken is C – Br because it is the weakest bond.

5. For each of the following reaction of carbonyl compounds, state the type of reaction and draw the
structure of the product(s).
(a)
(i) O
NaBH4

reduction
(ii)
HCN + NaCN
CHO

nucleophilic addition

Copyright of German Malaysian Institute. All rights reserved. 4

A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL

(iii)

Fehling’s solution
CHO
warm
oxidation
(iv) NO2

O2N NHNH2
O

condensation

(b) State the name and outline the mechanism for reaction (a)(ii).
Nucleophilic addition

Copyright of German Malaysian Institute. All rights reserved. 5