2014 Assessment Schedule AS 91165 (25) Demonstrate understanding of the properties of selected organic compounds

Question One

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(a) Br
CH3 C CH3
Br
CH3
THREE out of four
CH3 CH2 CH C OH
correct
O

pent2yne

3chloropentan1ol

(b) cyclohexane & cyclohexene BOTH pairs of

(i) Correct reagent cho- molecules dis-
either: using bromine water, Br2(aq) (cyclohexane and cyclohexene forms
sen for either (i) tinguished cor-
2 layers), the Br2(aq) remains orange, whereas the orange Br2(aq)
(Br2(aq) or rectly, i.e. both
turns colourless with cyclohexene.
MnO4/H+) or (ii) (i) and (ii) to-
or: using acidified potassium permanganate, MnO4 cyclohexane and cy- (moist litmus paper,
clohexene forms 2 layers, the MnO4/H+ remains purple whereas the One pair of mol- tally correct
metal or Na2CO3(aq))
purple MnO4/H+ turns colourless with cyclohexene. ecules distin-
guished correct-
(ii) aminoethane & ethanoic acid ly, i.e. either (i)
either: using moist red or blue litmus paper aminoethane will cause damp or (ii) totally
red litmus paper to turn blue, it will have no effect on damp blue correct
Correct observation
litmus paper. Ethanoic acid will cause damp blue litmus paper to
for one reaction in
turn red, it will have no effect on damp red litmus paper
either (i) or (ii)
or: using sodium carbonate (or bicarbonate) solution (or a metal eg Mg)
aminoethane will have no observable reaction with Na2CO3(aq) where-
as ethanoic acid will cause Na2CO3(aq) to effervesce / fizz / bubble
 Achievement with
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(c) 1chloropropane and 2chloropropane both react with KOH(aq) in EITHER:
a substitution reaction. The chloro atom (Cl) is replaced by a Elimination defined
hydroxyl group (OH). and linked correctly
KOH
one type of reaction and equations written
CH3CH2CH2Cl (
aq )
CH3CH2CH2OH correct, i.e. either OR
KOH KOH(aq) is substitu-
CH3CHClCH3 (
aq )
CH3CHOHCH3 Substitution defined
tion or KOH(alc) is
elimination and linked correctly
1chloropropane and 2chloropropane both react with KOH(alc) in and equations written Both reactions fully
an elimination reaction. A hydrogen atom (H) and the chlorine OR
one product is cor- discussed with a
atom (Cl) on adjacent carbon atoms are removed forming a carbon both reactions defined
rect, i.e. propan1 compare and contrast
to carbon double bond, C=C and linked correctly
ol, propan2ol or statement.
KOH( alc)
CH3CH2CH2Cl CH3 CH=CH2 + HCl propene with at least one equa-
KOH
tion OR
CH3CHClCH3 (
alc )
CH3 CH=CH2 + HCl one functional group All equations correct
correct, i.e. either with correct but limited
The substitution reactions of 1chloropropane and 2chloropropane alcohol or alkene definitions?
form 2 different alcohols propan1ol and propan2ol, whereas
the elimination reactions of 1chloropropane and 2chloropropane
form the 1 (same) alkene propene.
A3 3 from achieve-
N No response or no relevant evidence
ment M5 1 from merit E7 E and M
N1 1 from achievement
A4 4 from achieve- M6 2 from merit E8 2 E points
N2 2 from achievement
ment
Question Two
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(a) (i) (ii) OH
CH3 CH2 CH2
either both structural isomers
OH CH3 CH CH3 drawn correctly
TWO correct struc-
Structural (constitutional) isomers have the same molecular tures drawn AND cor-
formula (same type and number of atoms) but different rect definition of con-
or describes structural isomers stitutional isomers
structural formula (atoms are arranged differently). in terms of same number linked to molecules
These molecules both have the same number and type of and types atoms molecular
atoms but the atoms are arranged differently; C3H8O / the formula
hydroxyl/alcohol (OH) is on a different carbon atom.
(b) (i) either acidified potassium dichromate, Cr2O72/H+
or acidified potassium permanganate, MnO4/H+ (i) and (ii) correct colour
(ii) either colour changes from orange to green change for chosen solution
or colour changes from purple to colourless (i), (ii) and (iii) correct
(iii) correct product (butanoic
(iii) CH3 CH2 CH2 C OH acid) in
O
 Evidence Achievement with
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(c) cis CH3 OH trans CH H FOUR of the following
3
(i) links are made
C C C C Geometric isomers drawn
A C to C double bond
H H H OH causes the molecule
(ii) Geometric (cis and trans) isomers can occur in to be rigid (prevents
molecules that have (carbon to carbon) double bond rotation about the
because the carbon atoms are not free to rotate around bond)
(the axis of) the double bond. The carbon atoms Maximum of 2 CH3CHCHOH
(attached to the double bond) must also have two achieved points for contains a C to C
different groups attached to each carbon (involved in the ANY 2 valid state- double bond Geometric isomers fully
double bond). ments (may not quite discussed and linked to
CH3CHCHOH has 2
be at M level) why CH3CHCHOH,
different groups
CH3CHCHOH has a carboncarbon double bond. One attached to each of propen1ol, has
carbon of the double bond is attached to a hydrogen at- eg Geometric isomers geometric isomers
the double bonded
om (H) and a methyl group (CH3). The other is at- explained in terms of whereas CH3COHCH2,
carbons
tached to a hydrogen atom (H) and a hydroxyl/alcohol either the double bond propen2ol does not.
group (OH). being present Structural formula of
CH3COHCH2 drawn
CH3COHCH2 does not form geometric (cis and trans) eg different groups at- CH3COHCH2
isomers because although it contains a carboncarbon tached to the carbons on contains a C to C
double bond, one of the carbons attached to the double the double bond double bond
bond (C1) has 2 hydrogen atoms (H) attached to it.
CH3COHCH2 has a
CH3 H
(double bonded)
C C carbon with 2Hs
attached
OH H
N No response or no relevant evidence E7 only minor error /
A3 3 from achievement M5 2 from merit
N1 1 from achievement omission/ irrelevant info
A4 4 from achievement M6 3 from merit
N2 2 from achievement E8 all evidence given
 Question Three
Achievement with Achievement
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(a) CH3 CH3 CH3
(i)
C CH2 C CH2 C CH2 C C either (i) correct
CH3 CH3 CH3
(ii) OH
or (ii) correct
CH2 CH
(b)
A: CH3CH2CH2CH2OH (butan1ol)
(i)
B: CH3 CH CH2 CH3 (butan2ol) either A or B correct
OH
C: CH3 CH2 CH CH2 (but1ene) either C or D correct
D: CH3 CH CH CH3 (but2ene)
(ii) In an addition reaction. A hydrogen atom (H) and a hydroxyl group (OH) are
added to the adjacent carbon atoms of the carbon to carbon double bond, C=C,
forming a saturated alcohol. (addition) reaction
A butan1ol is the minor product and B butan2ol is the major product. explained in terms
either A (butan1ol) of formula of
There are 2 possible products because when the double bond is broken, a is identified as the products, and
hydrogen atom (H) will bond to one carbon (C) with either one or two minor product major and minor
hydrogen atoms attached and a hydroxyl group (OH) will bond with the other product with
carbon (C) with either two or one hydrogen atoms attached. or B (butan2ol) is reasons
In the major product the hydrogen (H) will bond to the carbon (C) with the identified as the
major product NOTE Markovnikovs
most hydrogen (H) atoms attached to it which is the first carbon of the four Rule is not an
carbon chain, as it has two hydrogen atoms attached to it rather than the second explanation
carbon which has one hydrogen atom attached to it.
Hence CH3CH2CHOHCH3 (butan2ol) is the major product.
 Achievement with
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(b) In an elimination reaction. A hydrogen atom (H) and the hydroxyl
(ii) group (OH) on adjacent carbon atoms are removed forming a carbon reason for major or
to carbon double bond, C=C. minor product correct (elimination) reaction A
for addition C forming explained
In the elimination reaction A C reason for major or in terms of formula of
minor product correct reactant and product
C CH3CH2CH=CH2 (but1ene) is neither a major nor minor for elimination
product since there is only one possible product.
In the elimination reaction B C + D
D CH3CH=CHCH3 (but2ene) is the major product and C
CH3CH2CH=CH2 (but1ene) is the minor product.
There are 2 possible products because the double bond may form The THREE reac-
between either the first and second carbons or the second and third tions in (b) (ii) are
carbons of the four carbon parent chain. The first carbon (C1) has either C (but1ene) (elimination) reaction ex- full elaborated on
three hydrogen atoms (3H) attached to it whereas the third carbon (C is identified as the plained in terms of formu-
3) has two hydrogen atoms (2H) attached to it. The major product minor product la of products, and major
will be the one in which the hydrogen atom (H) is removed from the and minor product with
carbon with the less number of hydrogen atoms attached to it. or D (but2ene) is reasons
In this case, D is the major product, as the double bond forms identified as the major
between the second carbon (C2) and the third carbon (C3) which NOTE Saytzeffs Rule is not
product an explanation
has two hydrogen atoms (H) attached to it. Since 2 < 3, this means
that D (but2ene) is the major product.
Whereas for C the double bond will form between the second carbon
(C2) and the first carbon (C1) which has three hydrogen atoms
attached to it. Since 3 > 2, this means that C (but1ene) will be the
minor product.
N No response or no relevant evidence E7 only minor error /
A3 3 from achievement M5 2 from merit omission/ irrelevant
N1 1 from achievement info
A4 4 from achievement M6 3 from merit
N2 2 from achievement E8 all evidence given
Judgment Statement

Not Achieved Achievement Achievement with Merit Achievement with Excellence

Score Range 07 8 13 14 18 19 24