practical: preparation of an ester

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STAGE 2 CHEMISTRY
ASSESSMENT TYPE 1: Investigations Folio
Practical Investigation: Preparation of an Ester.
Purpose
This task allows you to demonstrate your ability to prepare an organic compound. This
supervised assessment provides you with the opportunity to demonstrate your:

ability to manipulate apparatus using safe and ethical investigation procedures

ability to evaluate procedures with suggestions for improvements

ability to use appropriate chemistry terms, conventions, formulae and equations

skills in individual and collaborative work.
Description of assessment
Using the method provided on the attached sheet, this preparation will assess:

the well-organised, safe and effective manipulation of apparatus for reflux, distillation,
liquid-liquid extraction procedures

the quality of the product prepared

the chemical reasoning behind the procedures followed

the reasoning behind the suggested improvements

the correct use of chemical terms, conventions, formulae, and equations

skills in individual and collaborative work.
Assessment conditions
The preparation and the practical report will be completed, in lesson time, under supervision.
The preparation will be conducted in pairs, but individual reports will be written.
Page 1 of 6
Preparation
conducted
collaboratively
but individual
report written.
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
Stage 2 Chemistry Practical (S): PREPARATION OF AN ESTER
Practical is split
into three parts
(A, B and Report)
to allow for
completion,
under
supervision, in up
to three separate
periods.
The preparation and the practical report will be completed under supervision.
Aim: To prepare an ester and to purify it.
Materials:





Quickfit apparatus
measuring cylinders (10
mL, 25 mL)
glacial acetic acid (pure
ethanoic acid)
3-methyl-1-butanol
concentrated sulfuric acid





boiling chips
20 mL sodium carbonate
solution
fused calcium chloride
small conical flask &
stopper
200 C thermometer
Procedure:
Part A: Preparation of Ester
1.
Measure 15 mL of the alcohol provided and 10 mL glacial (pure) acetic acid into the
50 mL pear-shaped Quickfit flask.
2.
Slowly add about 1 mL concentrated sulfuric acid and a few boiling chips.
3.
Assemble the glassware for reflux.
4.
Reflux the mixture for 30 minutes.
Part B: Isolation of Pure Ester
5.
Pour the cooled mixture into a separating funnel which contains about 20 mL water.
Shake and allow the layers to separate.
6.
Collect the organic layer and wash it a second time with water.
7.
Collect the organic layer and wash it with about 20 mL sodium carbonate solution.
8.
Collect the organic layer and wash it with about 20 mL distilled water.
9.
Collect the organic layer in a small conical flask containing fused calcium chloride.
Stopper, swirl and allow to stand for 15 minutes.
10.
Decant the organic liquid into a clean, dry 50 mL pear-shaped flask and add boiling
chips.
11.
Assemble the glassware for distillation.
12.
Distil the ester, recording the boiling range of the fraction collected. The boiling
points of relevant chemicals are shown in the table below.
Boiling Point (C)
ethanoic acid
118
3-methyl-1-butanol
commercial grade ester
pure ester
sulfuric acid
13.
Page 2 of 6
Only the outline
of the procedure
is provided.
Student needs to
select, and use
effectively,
appropriate
apparatus for the
preparation and
isolation
procedures to
demonstrate
evidence of
careful, effective,
well-organised
and safe
investigation
procedures.
Allows students
to demonstrate
evidence of
constructive
collaborative
work skills.
Isolation
procedures
described without
explanation to
allow students to
demonstrate
evidence of skills
of analysis and
evaluation in the
separate report
against all levels
of the
performance
standards.
131
120 - 145
142
(approx) 142
Note the appearance and odour of the ester.
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
Part C: PRACTICAL REPORT
When you have completed your practical you are to write a practical report using the two
headings below and covering the material indicated under the two headings.
Note: The use of dot points is recommended.
Quality of product
contributes to
evidence of
careful and
effective
manipulation of
apparatus and
implementation
of procedures.
Results:

Record the boiling range of your distillate.

Present your product for the teacher to inspect.
Discussion:
In your discussion you should:


Write an equation for the reaction used and state the systematic name of the ester
formed.
Explain the purpose of:
 the reflux
 all isolation procedures, using equations where appropriate.

Explain why this method of preparation usually results in a poor yield of ester.

Suggest how the procedure could be modified to:
Open-ended
instructions in the
Discussion allow
students to
demonstrate
breadth of
evidence of
learning against
all levels of the
performance
standards.
 improve the yield of ester
 improve the purity of the ester.

Describe hazards associated with this preparation and the precautions taken to
ensure safety.
Additional comments

This assessment would contribute to the assessment of a student’s ability to use appropriate chemical
terms, conventions, formulae and equations.

Observation could be used to assess the student’s ability to:
manipulate apparatus to implement safe and ethical work procedures.
demonstrate skills in individual and collaborative work.
Page 3 of 6
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
Learning Requirements
Assessment Design Criteria
Capabilities
1. Demonstrate and apply
knowledge and
understanding of chemical
concepts and
interrelationships
2. Formulate questions,
manipulate apparatus,
record observations in
practical chemical
activities, and design and
undertake chemistry
investigations
3. Demonstrate an
understanding of how
knowledge of chemistry
can be used to make
informed conclusions or
decisions, taking into
account social and
environmental contexts
4. Develop possible solutions
to a variety of problems in
chemistry in new or familiar
contexts
5. Critically analyse and
evaluate chemical
information and procedures
from different sources
6. Communicate in a variety
of forms using appropriate
chemical terms and
conventions.
Investigation
Communication
Citizenship
Personal
Development
Work
Learning
Page 4 of 6
The specific features are as follows:
I1
Design of chemistry investigations plans.
I2
Selection and acknowledgment of information about
chemistry and issues in chemistry from different sources.
I3
Manipulation of apparatus and technological tools to
implement safe and ethical investigation procedures.
I4
The obtaining, recording, and display of findings of
investigations using appropriate conventions and formats.
Analysis and Evaluation
The specific features are as follows:
AE1 Analysis of data and concepts and their connections, to
formulate conclusions and make relevant predictions.
AE2 Evaluation of procedures, with suggestions for
improvement.
Application
The specific features are as follows:
A1
Application of chemistry concepts and evidence from
investigations to solve problems in new and familiar
contexts.
A2
Use of appropriate chemistry terms, conventions,
formulae, and equations.
A3
Demonstration of skills in individual and collaborative
work.
Knowledge and Understanding
The specific features are as follows:
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 and understanding of
chemistry in different forms.
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
Performance Standards for Stage 2 Chemistry
A
Investigation
Analysis and Evaluation
Application
Knowledge and
Understanding
Designs logical, coherent, and
detailed plans for chemistry
investigations.
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 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 wellorganised safe and ethical
investigation procedures.
Critically and logically evaluates
procedures and suggests a range
of 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.
Analyses data and their
connections with concepts, to
formulate generally appropriate
conclusions and make simple
predictions, with some relevance.
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.
Evaluates some procedures in
chemistry and suggests some
improvements that are generally
appropriate.
Uses generally appropriate
chemical terms, conventions,
formulae, and equations with some
general effectiveness.
Obtains, records, and displays
findings of investigations using
appropriate conventions and
formats accurately and highly
effectively.
B
Designs well-considered and clear
plans for 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.
Obtains, records, and displays
findings of investigations using
appropriate conventions and
formats mostly accurately and
effectively.
C
Designs considered and generally
clear plans for 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.
Applies generally constructive
individual and collaborative work
skills.
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.
Obtains, records, and displays
findings of investigations using
generally appropriate conventions
and formats with some errors but
generally accurately and effectively.
Page 5 of 6
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
D
Investigation
Analysis and Evaluation
Application
Knowledge and
Understanding
Prepares the outline of one or more
chemistry investigations.
Describes basic connections
between some data and concepts,
and attempts to formulate a
conclusion and make a simple
prediction that may be relevant.
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.
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.
For some procedures, identifies
improvements that may be made.
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.
Attempts to connect data with
concepts, formulate a conclusion,
and make a prediction.
Identifies a basic problem and
attempts to identify a solution in a
familiar context.
Demonstrates some limited
recognition and awareness of
chemistry concepts.
Acknowledges the need for
improvements in one or more
procedures.
Identifies some chemical terms or
formulae.
Shows an emerging understanding
that some chemistry information is
relevant to social or environmental
issues.
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.
Shows emerging skills in individual
and collaborative work.
Attempts to communicate
information about chemistry.
Attempts to record and display
some descriptive information about
an investigation, with limited
accuracy or effectiveness.
Page 6 of 6
Stage 2 Chemistry annotated task
Ref: A185246 (revised January 2013)
© SACE Board of South Australia 2013
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