NZIC 2012 Assessment Schedule for Chemistry 25 AS 91165 Demonstrate understanding of the properties of selected

organic compounds
One
(a)

Evidence

Achievement

CH3

Merit

Excellence

CH2CH3

2bromo3methylbutane
CH3 CH2 C OH

3 out of 5 names /
structures correct

Correct polymer

Both isomers
drawn

Constitutional

(structural)
isomers have the
same molecular
formula, different
structural formula

O
3chlorobutan2ol
either propan(1)amine
or (1)aminopropane
(b)
CH2

(c)
(i)

CH3
C

CH3

CH CH2

CH CH2 CH

CH3

CH3

CH3
C

cis
(ii)

CH3

H
C

CH3
trans

Constitutional (structural) isomers have the same number and type

of each atom (same molecular formula), but different atoms are
bonded to each other (different structural formula). Both but2ene
and methylpropene have the same constitutional (structural)
formula, C4H8, however their structural formulae are different.

Constitutional
isomerism of but2ene
and methylpropene
linked to the structure
of each molecule.

Full explanation of
constitutional
isomerism of but2ene
and methylpropene
linked to the structure
of each molecule.

Geometric (cistrans) isomerism occurs in molecules that have

carbontocarbon double bonds. The double bond restricts the
rotation of the atoms /groups of atoms about the axis of the carbon
tocarbon bond. Geometric isomers must also have two different

atoms / groups of atoms attached to each of the carbon atoms

involved in the double bond.
But2ene has a carbon to carbon double bond, and it has two
different groups (a methyl group and a hydrogen atom) attached to
each of the carbon atoms involved in the double bond.
Although methylpropene has a double bond that restricts rotation, it
cannot form geometric isomers because the two atoms attached to
each of the carbon atoms of the double bond are both the same i.e.
either both are hydrogen atoms or both are methyl groups

Geometrical
isomers must
have either a
CC or two
different atoms /
groups on each C
atom of the CC

N1: One correct

N2: Two correct
A3: Three correct
A4: Four correct

Requirement of

geometric isomerism
(double bond and two
different groups) linked
to reason why
either but2ene forms
geometric isomers
or methylpropene does
not form geometric
isomers.

M5: Meets criteria for

either structural or
geometric isomerism
M6: Meets criteria for
structural and
geometric isomerism

Full explanation of
geometric isomerism
(double bond, different
groups, atoms in fixed
positions due to non
rotation around double
bond) linked to both
molecules.

E7: both correct but minor

error or omission
E8: both correct

Two

Evidence

(a)
(i) H2 / Pt (high temperature and pressure)
(ii) Addition, because the double bond between the two
carbons has been broken and formed two new (single)
bonds (an unsaturated hydrocarbon has become saturated)
(b)
H H H
H

(c)

Cl

Achievement

H2 / Pt stated

Addition reaction with

a reason

Correct product

H H H
In an elimination reaction two atoms or small groups are
removed from a molecule forming a double bond in the
molecule. (a saturated molecule has become unsaturated)

In a substitution reaction one atom or group of atoms is

replaced by another atom or group of atoms.

Bromoethane undergoes a substitution reaction with

(aqueous / concentrated) NH3. The Br in bromoethane is
replaced with NH2. The products are aminoethane
(ethanamine) and hydrogen bromide
CH3CH2Br + NH3

CH3CH2NH2 + HBr

Bromoethane undergoes an elimination reaction with

alcoholic KOH. A hydrogen atom and a bromine atom are
removed from the molecule as HBr and a double bond is
formed between the two carbon atoms. The products are
ethene and hydrogen bromide.
CH3CH2Br

Definition of either an
elimination or a
substitution reaction

Equation for either an

elimination or
substitution reaction

Merit

Excellence

Addition reaction with

reason AND part (i)
correct

Addition reaction with

reason AND part (i)
correct

Definition of
elimination reaction
linked to alcoholic
KOH and equation for
elimination

Explanation of
elimination reaction
linked to alcoholic
KOH and equation for
elimination

Definition of
substitution reaction
linked to NH3 and
equation for
substitution

Explanation of
substitution reaction
linked to aqueous NH3
and equation for
substitution

CH2=CH2 + HBr
N1: One correct
N2: Two correct
A3: Three correct
A4: Four correct

M5: Meets criteria for

TWO reactions
M6: Meets criteria for
THREE reactions

E7: all reactions explained

but minor error or
omission
E8: all reactions explained
fully

Three
(a)

Evidence
CH3 CH CH2 CH3

Achievement

Cl
because the Cl is
attached to a C that is bonded to 2 other C
atoms

(b)
H

CH3

OH OH

R1 either H2O/H+ or dilute H2SO4

Br

2 chloroalkane
circled with a reason

1 Propene product,
i.e. P1, P3 or P4

Oxidation of
propanol product,
i.e. P2

1 Reagent correct,
i.e. R1 or R2

1
H

R2 either KOH(aq) or NaOH(aq)

H H
OH H H
CH3

Br H

CH3

P2

4
3
Propene reacts with HBr to form two products, as the molecule is
unsymmetrical. A major and a minor product forms, as the bromine
atom can add to either the first or second carbon atom making two
different products. The major product occurs when the hydrogen
Reason for major
atom adds to the carbon atom (the 1st carbon) in the double bond
and minor products
that already has the most hydrogen atoms attached to it. Therefore
the bromine atom adds to the second carbon atom. The minor
product has the hydrogen atom added to the second carbon atom
and the bromine to the first carbon atom.
N1: One correct

Merit

Reaction for
propene with HBr
(P3 and P4),
another reaction
(either P1 or P2)
and one reagent
(either R1 or R2)
correct

Reason for major

and minor products

Excellence

Reaction scheme
complete, i.e. P1,
P2, P3, P4, R1 and
R2 correct

Reason for major

and minor products
linked to structures

N2: Two correct

M5: One correct

E7: reaction scheme

correct

A3: Three correct

M6: Two correct

E8: Two correct

A4: Four correct

Question 4 Evidence
Add a piece of red and blue litmus to a sample of each of the
four unknowns.
The sample that changes red litmus to blue is aminoethane
(ethanamine). The other three samples have no effect on
litmus.

Achieved
Reaction of one sample
with all reagents to
enable sample to be
distinguished.

Merit
Three samples
identified.

Excellence
Valid method that identifies
each sample linked to the
reagent used, observations
and equations.

Using fresh samples of the 3 remaining unknowns, add a few

drops of bromine water. Pentene will decolourise the orange
bromine water, pentane will form two layers and ethanol will
not react.
C5H10 + Br2 C5H10Br2
Using fresh samples of the 2 remaining unknowns, add
acidified potassium dichromate and warm gently. One sample
will turn from orange to green, the other will remain orange
and from two layers.
The sample that changes the colour of acidified potassium
dichromate is ethanol. Pentane is insoluble in acidified
potassium dichromate.
CH3CH2OH

Cr2O72/H+

CH3COOH

Judgement Statement:

N1: One reaction

described
N2: Two reactions
described
A3: Meets criteria
A4: Three reactions
described

M5: Two samples

identified.
M6: Meets criteria.

E7: All samples identified

but minor error or omission
E8: Meets criteria.

Achieved with Achievement

Achieved with Merit

Achieved with Excellence

Score: 9 16

Score: 17 18

Score: 25 32