NCEA Level 2 Chemistry (90309) 2010 — page 1 of 4
Assessment Schedule – 2010
Chemistry: Describe the structural formulae and reactions of compounds containing
selected organic functional groups (90309)
Evidence Statement
Q
ONE
(a)
Evidence
Achievement
Structural formula
IUPAC name
TWO of
CH3CH2CH2CH2COOH
pentanoic acid
CH3CH2COOCH2CH3
ethyl propanoate
• THREE names
or structures
correct.
3-methylbut-1-yne
Achievement
With Merit
Achievement with
Excellence
Three linked
explanations of
(1), (2), (3), (4).
A full discussion of
structural isomers,
linked to molecules
C and D, AND
geometric isomers
linked to the
structure of
molecule A.
2-chlorobutan-2-ol
(b)(i)
C and D
(1) They have the same molecular formula
C7H14, the same number of carbon and
hydrogen atoms, but their atoms are arranged
differently.
(ii)(1)
(2)
A
(cis-hex-2-ene)
(trans-hex-2-ene)
(3)
(2) Cis-trans isomers occur in molecules that
have carbon-to-carbon double bonds because
rotation of the atoms about the axis of the
carbon-to-carbon double bond is restricted.
(3) They must also have two different groups
attached to each of the carbons involved in the
double bond.
(4) Molecule A, hex-2-ene, has a double bond.
It has two different groups attached to the
carbons, i.e. one carbon of the double bond is
attached to H and CH3 and the other carbon is
attached to H and CH2CH2CH3.
• Correct
structural
isomers
identified.
• Molecule that
can exist as cistrans isomers
identified and
isomers drawn.
NCEA Level 2 Chemistry (90309) 2010 — page 2 of 4
TWO
(a)(i)
CH3 – CH = CH2
Elimination
THREE of
• TWO products
or two reaction
types.
(ii)
BOTH of
Two products
identified and
linked to reaction
type. (Two pairs,
reaction type and
structure correct.)
Esterification/elimination
(iii)
• Polymer drawn
correctly.
(b)
(c)
AND
CH3–COOK or CH3–COO–K+
Acid-base
Both reactions are addition reactions. This
involves breaking the double bond between
the carbon atoms in but-1-ene and forming a
single bond in its place, as well as forming
two new single bonds.
With Cl2, the new single bonds formed are
both C–Cl bonds.
With HCl, the new single bonds are a C–Cl
bond and a C–H bond.
• Description of
addition
reaction, or
recognises
Markovnikov’s
rule.
With Cl2
But-1-ene reacts to form one product
CH3–CH2–CH=CH2 + Cl2 
CH3–CH2–CHCl–CH2Cl
• One product for
but-1-ene with
either Cl2 or
HCl.
EITHER
But-1-ene reacts
with Cl2 to form
CH3-CH2-CHClCH2Cl.
Linked to an
addition reaction.
But-1-ene reacts
with Cl2 to form
CH3–CH2–CHCl–
CH2Cl
OR
AND
With HCl
But-1-ene reacts to form two products.
This is because but-1-ene is an asymmetric
alkene (one carbon atom of the double bond
has different groups attached to it).
CH3–CH2–CHClCH3 is the major product
because the H from HCl will bond to the
carbon atom with the greatest number of H
atoms.
CH3–CH2–CH=CH2 + HCl 
CH3–CH2–CHClCH3 (major product)
CH3–CH2–CH2–CH2Cl (minor product)
But-1-ene reacts
with HCl to form
CH3–CH2–
CHClCH3 (major
product) and
CH3–CH2–CH2CH2Cl (minor
product).
Linked to an
addition reaction.
But-1-ene reacts
with HCl to form
CH3–CH2–
CHClCH3 (major
product) and
CH3–CH2–CH2–
CH2Cl (minor
product)
Linked to an
explanation of an
addition reaction
(breaking of double
bond and drawing
correct structures
suffices here) and
the formulae of
products.
NCEA Level 2 Chemistry (90309) 2010 — page 3 of 4
THREE
(a)(i)
(ii)
(b)(i)
(ii)
Secondary.
The carbon that the OH group is
attached to, is attached to two other
carbons.
TWO of
• One alcohol correctly
classified and the
reason described.
Primary.
The carbon that the OH group is
attached to, is attached to only one other
carbon.
One of these groups circled:
• Functional group
correct.
Bromine water rapidly decolourised
from orange to colourless.
• Observation described.
(iii)
• ONE correct product
for hydrolysis reaction.
TWO correct
products for
hydrolysis reaction.
FOUR
Add Na2CO3 to a sample of each
organic substance. The substance which
produces bubbles is the propanoic acid.
The bubbles are CO2.
2CH3CH2COOH + Na2CO3 
2CH3CH2COONa + CO2 + H2O
Add MnO4-/H+ to the two remaining
samples. One of the two samples will
turn the solution from purple to
colourless. This is hex-1-ene.
The organic substance that does not
change the colour of acidified
potassium permanganate nor reacts with
sodium carbonate is hexane.
One molecule identified
with correct reagent and
observation.
Two molecules
identified with
correct reagent and
observation.
(Allow a statement
that hexane does
not react with either
reagent as
indentifying a
molecule).
OR
One molecule
identified with
correct reagent,
observation and
equation.
THREE correct
products for
hydrolysis
reaction.
Valid method
that identifies
each sample.
This includes
reagent used,
observations and
equations.
NCEA Level 2 Chemistry (90309) 2010 — page 4 of 4
Judgement Statement
Achievement
Achievement with Merit
Achievement with Excellence
3A
OR
1M/E+1A
3M
3E