CHEMISTRY 2.5
An assessment for AS90309
Describe the structural formulae and reactions of compounds containing selected
organic functional groups.
Credits: Four
INSTRUCTIONS
Answer ALL questions.
© New Zealand Institute of Chemistry 2006
2
You should spend about 40 minutes on this assessment
QUESTION ONE:
Names and functional groups
(i) Complete the following table showing the structural formulae, IUPAC (systematic) names,
and the functional group name for some organic compounds.
Structural formula
(a)
CH3
IUPAC name
Functional group name
CH3
CH
OH
(b)
CH3
C
CH
CH3
CH3
(c)
H
C
C
CH2
CH3
(d)
propyl methanoate
(e)
pentanoic acid
carboxylic acid
2,2-dichlorobutane
haloalkane
(f)
(ii) Circle the answer which best classifies the molecule drawn in part (a) of the above table:
Primary
Secondary
Tertiary
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3
QUESTION TWO:
(a)
Isomerism
There are three structural isomers of the alkene which has the molecular formula C4H8 .
(i) State what is meant by the term structural isomer:
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(ii) In the box below draw the three structural isomers of the alkene which has the
molecular formula C4H8 .
(b)
The compound CH3CCl = CHCl exhibits geometrical isomerism. Draw and name the
geometrical isomers of this molecule:
Name: ________________________
Name: ________________________
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(c)
CH3CH = CCl2 is a structural isomer of CH3CCl = CHCl but it does not exhibit geometric
isomerism. Account for this difference.
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QUESTION THREE:
Organic Reactions
Complete the following equations by drawing the structural formula of the organic products in the
boxes provided.
a.
CH3 CH
CH
CH3
H2 / Pt
CH3
b.
CH3
C
CH2
H
OH
Conc H2SO4
& heat
OH
c.
+
CH3 C
CH3 CH2 CH2 OH
O
Conc H2SO4
& heat
CH3
d.
C
CH2
KMnO4 (aq)
CH3
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QUESTION FOUR:
(a)
Distinguishing Compounds
(i) Identify a reagent that could be used to distinguish between cyclohexane and
cyclohexane.
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(ii) Describe the expected observations for cyclohexene and cyclohexane.
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(b)
Discuss why cyclohexene and cyclohexane react differently in the test described above.
Your answer should include:
 The nature of the functional groups
 The types of reactions involved
 Equations for any reactions discussed
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QUESTION FIVE:
Organic Reaction Scheme
The flow diagram below shows a series of organic reactions.
Complete the diagram by:
 Drawing structural formulae and writing IUPAC (systematic) names
for compounds A and B.
 Name C and identify reagent D.
 Draw the structural formula only for compound E.
CH3
CH3 CH
CH
CH2
3-methylbut-1-ene
HCl
Compound B:
Compound A:
Name:
Name:
NaOH
Compound C:
Reagent D: _____________
CH3
CH3
CH3
CH3 CH CH2
CH CH2
CH2
OH
Name:
C
OH
O
3-methylbutanoic acid
NaOH
Compound E:
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QUESTION SIX:
Polymerisation
Plastic or Latex paint that is used to paint the exterior of a house may contain the polymer known
as polyvinyl acetate (PVA). This polymer, PVA is based on the monomer vinyl acetate which is
shown below:
O
H
O
C
H
C
CH3
C
H
vinyl acetate
Draw a section of the polymer PVA that shows exactly TWO monomer units.
END OF ASSESSMENT
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