PRE-UNIVERSITY & GENERAL STUDIES
GMI GERMAN UNIVERSITY PREPARATORY PROGRAM
GAPP 2020
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 H3C—CH2—CH2—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,
(ii) electrophilic addition,
(iii) elimination
(b) In reaction 2, the aqueous OH– acts as a nucleophile.
(i) State what is meant by the term nucleophile.
(ii) With the aid of curly arrows, draw the mechanism involved in reaction 2. Show any relevant dipoles.
(c) Compounds B and D are structural isomers of each other.
(i) State what is meant by the term structural isomers.
(ii) Draw the skeletal formulae of compounds B and D.
(d) Compound C can be polymerised to form compound E. Draw a section of compound E. Show two repeat
units.
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.
(b) Name compound E.
(c) Compound E can be oxidised to form a carboxylic acid.
(i) State a suitable oxidising mixture for this reaction.
(ii) Write a balanced equation for this oxidation of compound E. Use [O] to represent the oxidising
mixture.
(iii) Explain how compound E and the carboxylic acid could be distinguished by infra-red spectroscopy.
(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.
A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL
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.
(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.
(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.
(d) Acrylic acid reacts with prop-2-en-1-ol to produce an ester.
(i) Write the balanced equation for this reaction.
(ii) Draw the structure of the ester. Clearly display all of the functional groups.
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.
(ii) Calculate the number of moles of (CH3)2CHCH2Br collected.
(iii) Calculate the percentage yield. Give your answer to three significant figures.
(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.
(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.
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A LEVEL CHEMISTRY AS ORGANIC – TUTORIAL
(a) 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.
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
(ii)
HCN + NaCN
CHO
(iii)
Fehling’s solution
CHO
warm
(iv) NO2
O2N NHNH2
O
(b) State the name and outline the mechanism for reaction (a)(ii).
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