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SOUTH AUSTRALIAN MATRICULATION

2012 APRIL INTAKE ASSESSMENT 3


ORGANIC AND BIOLOGICAL CHEMISTRY AND CHROMATOGRAPHY

CHEMISTRY
Name

: _____________________________________

Student No. : _____________________________________


Group

20 pages
5 questions

: _____________________________________

Time: 90 minutes
Approved dictionaries and calculators may be used.
Instructions to Candidates
1. Answer ALL questions.
2. There is no need to fill all of the space provided; clear, well-expressed answers are
required. If you delete part or all of an answer you should clearly indicate your final
answer.
3. The total mark is 70.

Question

Marks

/16m

/16m

/13m

/13m

/12m

TOTAL

/70m

Purpose:
This task allows you to demonstrate your knowledge and understanding of the concepts of organic and
biological chemistry.
Description of the assessment:
This test assesses:
1) knowledge and understanding of the concepts of organic chemistry
2) use of systematic nomenclature
3) interpretation and use of structural formulae
4) knowledge and understanding of the nature and reactions of the functional group studied
5) application of concepts to solve problems in familiar and unfamiliar contexts
6) knowledge and understanding of practical procedures - chemical synthesis & organic testing
7)
Assessment conditions:
1) Time allowance: 90 minutes
2) You may consult the periodic table.
Assessment Design Criteria

Analysis &
Evaluation
(AE)

Application
(A)

Knowledge &
Understanding
(KU)

Grade

AE1

Analysis of data and concepts and their


connections, to formulate conclusions and make
relevant predictions.

AE2

Evaluation of procedures, with suggestions for


improvement.

A1

Application of chemistry concepts and evidence


from investigations to solve problems in new and
familiar context.

A2

Use of appropriate chemistry terms, conventions,


formulae and equations.

A3

Demonstration of skills in individual and collaborative


work.

KU1

Demonstration of knowledge and understanding of


chemistry concepts.

KU2

Use of knowledge of chemistry to understand and


explain social or environmental issues.

KU3

Communication of knowledge of chemistry in different


formats

OVERALL GRADE

Performance Standards for Stage 2 Chemistry Assessment 3


Investigation

Designs logical, coherent, and detailed


chemistry investigations.
Critically and logically selects and consistently
and appropriately acknowledges information
about chemistry and issues in chemistry from
a range of sources.
Manipulates apparatus and technological tools
carefully and highly effectively to implement
well-organised safe and ethical investigation
procedures.

Analysis and Evaluation

Application

Knowledge and Understanding

Critically and systematically


analyses data and their
connections with concepts, to
formulate logical and perceptive
conclusions and make relevant
predictions.

Applies chemistry concepts and


evidence from investigations to
suggest solutions to complex
problems in new and familiar
contexts.

Consistently demonstrates a deep


and broad knowledge and
understanding of a range of
chemistry concepts.

Critically and logically evaluates


procedures and suggests a
range of appropriate
improvements.

Obtains, records, and displays findings of


investigations using appropriate conventions
and formats accurately and highly effectively.
B

Designs well-considered and clear chemistry


investigations.
Logically selects and appropriately
acknowledges information about chemistry
and issues in chemistry from different sources.
Manipulates apparatus and technological tools
carefully and mostly effectively to implement
organised safe and ethical investigation
procedures.

Clearly and logically analyses


data and their connections with
concepts, to formulate
consistent conclusions and
make mostly relevant
predictions.
Logically evaluates procedures
and suggests some appropriate
improvements.

Uses appropriate chemical terms,


conventions, formulae, and
equations highly effectively.

Uses knowledge of chemistry


perceptively and logically to
understand and explain social or
environmental issues.

Demonstrates initiative in applying


constructive and focused
individual and collaborative work
skills.

Uses a variety of formats to


communicate knowledge and
understanding of chemistry
coherently and highly effectively.

Applies chemistry concepts and


evidence from investigations to
suggest solutions to problems in
new and familiar contexts.

Demonstrates some depth and


breadth of knowledge and
understanding of a range of
chemistry concepts.

Uses appropriate chemical terms,


conventions, formulae, and
equations effectively.

Uses knowledge of chemistry


logically to understand and explain
social or environmental issues.

Applies mostly constructive and


focused individual and
collaborative work skills.

Uses a variety of formats to


communicate knowledge and
understanding of chemistry
coherently and effectively.

Applies chemistry concepts and


evidence from investigations to
suggest some solutions to basic
problems in new or familiar
contexts.

Demonstrates knowledge and


understanding of a general range of
chemistry concepts.

Obtains, records, and displays findings of


investigations using appropriate conventions
and formats mostly accurately and effectively.
C

Designs considered and generally clear


chemistry investigations.
Selects with some focus, and mostly
appropriately acknowledges, information about
chemistry and issues in chemistry from
different sources.
Manipulates apparatus and technological tools
generally carefully and effectively to implement
safe and ethical investigation procedures.

Analyses data and their


connections with concepts, to
formulate generally appropriate
conclusions and make simple
predictions, with some
relevance.
Evaluates some procedures in
chemistry and suggests some
improvements that are
generally appropriate.

Applies generally constructive


individual and collaborative work
skills.

Obtains, records, and displays findings of


investigations using generally appropriate
conventions and formats with some errors but
generally accurately and effectively.
D

Prepares the outline of one or more chemistry


investigations.
Selects and may partly acknowledge one or
more sources of information about chemistry
or an issue in chemistry.
Uses apparatus and technological tools with
inconsistent care and effectiveness and
attempts to implement safe and ethical
investigation procedures.

Describes basic connections


between some data and
concepts, and attempts to
formulate a conclusion and
make a simple prediction that
may be relevant.
For some procedures, identifies
improvements that may be
made.

Obtains, records, and displays findings of


investigations using conventions and formats
inconsistently, with occasional accuracy and
effectiveness.
E

Identifies a simple procedure for a chemistry


investigation.
Identifies a source of information about
chemistry or an issue in chemistry.
Attempts to use apparatus and technological
tools with limited effectiveness or attention to
safe or ethical investigation procedures.
Attempts to record and display some
descriptive information about an investigation,
with limited accuracy or effectiveness.

Uses generally appropriate


chemical terms, conventions,
formulae, and equations with
some general effectiveness.

Attempts to connect data with


concepts, formulate a
conclusion, and make a
prediction.
Acknowledges the need for
improvements in one or more
procedures.

Uses knowledge of chemistry with


some logic to understand and
explain one or more social or
environmental issues.
Uses different formats to
communicate knowledge and
understanding of chemistry with
some general effectiveness.

Applies some evidence to


describe some basic problems
and identify one or more simple
solutions, in familiar contexts.

Demonstrates some basic


knowledge and partial
understanding of chemistry
concepts.

Attempts to use some chemical


terms, conventions, formulae, and
equations that may be
appropriate.

Identifies and explains some


chemistry information that is
relevant to one or more social or
environmental issues.

Attempts individual work


inconsistently, and contributes
superficially to aspects of
collaborative work.

Communicates basic information to


others using one or more formats.

Identifies a basic problem and


attempts to identify a solution in a
familiar context.

Demonstrates some limited


recognition and awareness of
chemistry concepts.

Identifies some chemical terms or


formulae.

Shows an emerging understanding


that some chemistry information is
relevant to social or environmental
issues.

Shows emerging skills in


individual and collaborative work.

Attempts to communicate
information about chemistry.

QUESTION 1
Plants under stress produce chemicals.
(a)

When grass is cut, a series of chemical reactions follow, beginning with the hydrolysis of
triglycerides into fatty acids and alcohol. The structural formula of one such triglyceride is
shown below:

(i)

Draw the structural formula of the alcohol formed in the hydrolysis of the above
triglyceride.

( 2 marks)

(ii)

Triglyceride may be hydrogenated under high pressure.


(1)

State one other reaction conditions used in the hydrogenation process.


(1 mark)

(2)

Identify one change that hydrogenation causes in a physical property of a


triglyceride.

(1 mark)

(3)

State the structural change in the triglyceride molecule that results in the
change in physical property.

(1 mark)

(iii)

The fatty acid is then converted into 2 compounds with the structural formulae
shown below:

Describe a chemical test that can be used to distinguish compound A from


compound B.

(3 marks)

(b)

Jasmonic acid is another molecule produced by plants under stress. The structural
formula of jasmonic acid is shown below:

(i)

Name the functional group circled in the structural formula above.


(1 mark)

(ii)

Jasmonic acid undergoes addition reaction.


(1)

Draw the structural formula of the product formed when Jasmonic acid
undergoes an addition reaction with bromine.

(2 marks)
(2)

State the observation in part (ii)(1) above.

(2 marks)

(iii)

Predict and explain the solubility of jasmonic acid in water.

(3 marks)

TOTAL: 16 marks

QUESTION 2
(a)

Compound X below is responsible for the odour of Cheddar Cheese:

Compound X
(i)

State the systematic name of compound X.


(2 marks)

(ii)

Compound X is a weak acid.


Write an equation to show the ionization of compound X in water.

(2 marks)

(iii)

Compound X oxidises from an aldehyde. Draw the structural formula of this aldehyde.

(2 marks)

(b)

Compound Y is responsible for the flavour in Brie Cheese.


Compound Y can be made by oxidising alcohol P as shown below:

Compound Y
(i)

State the whether alcohol P is classified as primary, secondary or tertiary.


(1 mark)

(ii)

An acidified solution containing a manganese anion is the reagent used in the laboratory
to oxidise alcohol P to compound Y.
(1)

Name the manganese anion used.


(1 mark)

(2)

State the conditions required to synthesise compound Y.

(2 marks)

(iii)

A student mixed 1 mL of Tollens Reagent with 5 drops of Compound Y in a test tube.


Predict the observation for this reaction.
(1 mark)

(c)

Ascorbic acid and ethyl pentanoate are two esters that are often used as flavoring agent. The
structural formula of ascorbic acid is shown below:

Ascorbic acid
(i)

Draw the structural formula of ethyl pentanoate.

(2 marks)

(ii)

Ascorbic acid is heated with NaOH solution.


Draw the structural formula of the product(s) formed after this reaction.

(3 marks)
TOTAL: 16 marks

QUESTION 3
Cellulose is found in plant cell. Cellulose is tasteless, odourless, hydrophilic, insoluble in water and
most organic solvents. It can be broken down chemically into its glucose units by treating it with
concentrated acids at high temperature.

(a)

Draw the structural formula of one glucose molecule from which cellulose is produced.

(2 marks)

(b)

Write a balanced equation to show how cellulose is broken down to form dissacharide.

(2 marks)

(c)

Glucose produced by the breakdown of cellulose can be converted into ethanol by fermentation
with the help of enzyme zymase.
(i)

Write an equation to show the production of ethanol by the fermentation of glucose.

(2 marks)

(ii)

Explain why combustion of ethanol produced from fermentation will not add more CO 2 into
the atmosphere.

(1 mark)

(iii)

State one condition required for fermentation process, other than yeast to provide zymase
enzyme.
(1 mark)

(iv) After fermentation process, the mixture containing ethanol is decant into a reaction flask
and purification process is carried out using distillation set-up as shown below:

Discuss by referring to one mistake in this distillation set-up and how it can affect the pure
ethanol collected.

(2 marks)

(d)

Predict and discuss the solubility between compound P and compound Q.

compound P

compound Q

(3 marks)

TOTAL: 13 marks

QUESTION 4
(a)

Saccharin, an artificial sweetener, is used to sweeten products such as drinks, candies,


cookies, medicines and toothpastes.

saccharin
(i)

Give the molecular formula of saccharin.


(2 marks)

(ii)

Name the functional group circled on the diagram above.


(1 mark)

(iii)

Saccharin is refluxed with diluted HCl solution.


(1)

Name the type of reaction between saccharine and HCl solution


(1 mark)

(2)

Draw the structural formula of the product formed after the reflux.

(2 marks)

(iv)

Saccharin is usually used in the form of its sodium salt.

Explain why the usage of sodium salt of saccharin is more favourable than its
molecular form in manufacturing soft drinks.

(2 marks)

(b)

The diagram below shows a section of a polypeptide chain.

(i)

Polypeptide chain can be broken down by protease (a digestive enzyme) into many
amino acids.
(1)

State the number of amino acids used to construct this section of the
polypeptide chain.
(1 mark)

(2)

Draw the structural formula of one of the amino acid formed after the
polypeptide chain is broken down by protease (a digestive enzyme that splits
proteins).

(2 marks)

(ii)

The polypeptide interacts with another polypeptide chain adjacent to it.

(1)

Name the type of interaction formed between the side groups circled on the
diagram.
(1 mark)

(2)

State the type of structure in which the interaction in part (1) contribute to the
polypeptide (primary, secondary, tertiary, quaternary).
(1 mark)

TOTAL: 13 marks

QUESTION 5
(a)

The types of sugar present in an orange juice sample can be separated and identify by TLC
using ethanol as the solvent and octadecylsilane as the stationary phase.
One chromatogram is shown in the diagram below:

(i)

State how many types of sugar present in this orange juice sample.
(1 mark)

(ii)

On the diagram, indicate solvent front.

(1 mark)

(iii)

Explain why this analysis is not effective, and suggest an improvement to this
analysis.

(2 marks)

Credit will be given for answers to part (b), which show clear well-expressed ideas, and which
present accurate and relevant information in a well-organised, logical manner. Your answer
should be confined to the space provided and should take approximately 10 minutes.
(b)

Benzoic acid, benzyl alcohol and benzaldehyde present in an organic sample can be
separated and identify by Gas Chromatography using a column packed with inert solids that
are coated with high boiling point hydrocarbon and helium as the carrier gas.
The structural formula of benzoic acid, benzyl alcohol and benzaldehyde are shown below:

benzoic acid

benzyl alcohol

benzaldehyde

The chromatogram obtained is shown in the diagram below:

By referring to the polarities of the three organic compounds, discuss their relative strengths
of attractions for stationary phase and the mobile phase and the relative rates of their
movement along the stationary phase. Hence, predict and explain peak A, B and C.

(8 marks)

TOTAL: 12 marks

You may write on this page if you need more space to finish your answers to this
Question Booklet. Make sure to label each answer carefully (eg.3(e)continued).