Using a Dialectic Soft Systems Methodology (DSSM) to
construct a Template for Answering Organic Deductive
Questions in Advance Level Chemistry
Aileen Lim
Low Kian Seh
Tearle Cheng
Tng Miao Hui and
Li Xuanjun
Temasek Junior College
Abstract
Organic deductive questions are examined regularly in major examinations. However many students
find it difficult to grasp the techniques of answering organic deductive questions and thus unable to
score in examinations. This paper reveals the application of Dialectic Soft Systems Methodology in
constructing a template for helping college students in answering Organic Deductive Questions in
Advance Level Chemistry Examination. Apart from serving as a guided and structured approach for
memorizing chemical reactions, frequent practice in its manipulation enables the students to acquire the
necessary skills for answering deductive Organic Chemistry questions in examinations. This in turn
empowers their knowledge in organic chemistry to go beyond a nodding acquaintance with notions
and notations
Introduction
Organic Chemistry is a study on molecules made of carbon, and to see what kinds of reactions they
undergo, and how they are put together. As pointed out by Winter (2005), when these principles are
known, that knowledge can be put to good use, to make better drugs, stronger plastics, better materials
to make smaller and faster computer chips, better paints, dyes, coatings, and polymers that help improve
the quality of life. Thus, organic chemistry is a major component to be tested in Chemistry at General
Certificate of Education Advanced level (GCE A level) examination and 41.6% of examination
questions are focused on Organic Chemistry. Organic deductive questions appear regularly in this
examination. In Singapore, students from junior colleges will take the GCE A level examinations at the
end of their two years of study.
However many students are unable to score well in organic deductive questions due to their inability
to grasp the following answering techniques: recognizing key properties or reactions that are related to
the functional groups of compounds; linking the key properties or reactions to the functional groups of
the compounds; expressing answers in a coherent manner, and piecing the functional groups together
to form the structure.
The current practice of teaching students to answer organic deductive questions is via a lecture-tutorial
system. After attending lectures, students are tasked to solve a few sample organic deductive questions
during tutorials and the tutors will point out techniques in solving the questions verbally via flowcharts
and discussions with
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students. Some of the discussion points in tutorial class include identifying key things to look out for;
deducing the functional groups and properties; piecing the deductions together to come up with the
final structure and phrasing the answers appropriately. Although the current lecture-tutorial system
aims to improve students’ results in answering deductive questions by enabling them to better grasp and
apply the techniques of answering organic deductive questions basing on sample questions selected for
tutorials, a number of students are still unable to grasp techniques to solve organic deductive questions
two to three months before the GCE A level examinations. It is realised that a student’s knowledge in
Organic Chemistry must go beyond a nodding acquaintance with its notions and notations. Even if
Organic Chemistry is to remain merely a tool for that student, he or she will never be its master until
he or she has understood why it is so formed and is practiced in its manipulations. Fuelled by this
motivation, the research team embarks on a journey that uses Dialectic Soft Systems Methodology
(DSSM) to construct a template for helping students in answering deductive questions in Organic
Chemistry.
This paper describes the use of DSSM in constructing a template for the answering of organic
deductive questions. DSSM allows us to collect and use gathered data to answer our questions
concerning the problems faced by students when solving organic deductive questions and how can
we help to overcome the problems. By analyzing the data we gathered from students, we are thus able
to derive a template for the answering of organic deductive questions, which is further refined after
putting it into practice. The success of the use of the template in answering organic deductive questions
is then evaluated.into practice. The success of the use of the template in answering organic deductive
questions is then evaluated.
Nonetheless it must be noted that the learning styles of students vary and some students may be
unreceptive to using a template. The learning attitude of students and their grasp of concepts in organic
chemistry also play an important role in determining the outcome of this project. Since this is a new
method in teaching of answering organic deductive questions, there may be difficulties faced in
integrating this new system to the current teaching method. It may also be difficult to get the teachers
to teach in the same mode of instruction. Factors like time and resources required to implement this
project are also our concerns.
Nonetheless it must be noted that the learning styles of students vary and some students may be
unreceptive to using a template. The learning attitude of students and their grasp of concepts in organic
chemistry also play an important role in determining the outcome of this project. Since this is a new
method in teaching of answering organic deductive questions, there may be difficulties faced in
integrating this new system to the current teaching method. It may also be difficult to get the teachers
to teach in the same mode of instruction. Factors like time and resources required to implement this
project are also our concerns.
Justifications for adopting Dialectic Soft Systems Methodology
As pointed out in the work of Tay and Lim (2007), Dialectic Soft Systems Methodology (DSSM) is not
a new form of Checkland’s Soft Systems Methdology. It is the same process as the “7-stage” description
except it is presented from a different perspective. This approach makes explicit the inherent cyclic
nature of Checkland’s seven stages and the use of dialectic comparisons. It progresses through four
dialectics (see Figure 1).
Our design of the template using a Dialectic Soft Systems Methodology (DSSM) aims to
enable students to better grasp and apply the techniques of answering deductive questions
in organic chemistry. The template provides useful information in relation to the different
tests and reactions of various functional groups that students can use to help them solve
deductive questions. In traditional teaching of organic chemistry, materials are taught in
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lecture and students are expected to solve tutorial questions before lesson. Tutors will go through and
discuss the questions during tutorials. However, their tutorials, quizzes, and examinations showed a
general lack of root comprehension. The majority of the students appeared to understand the material
after lectures but fail to integrate and apply information when comes to more challenging deductive
questions.
Tay and Lim (2004) highlighted the usefulness of a scenario-based training system in helping new
trainees to learn, rehearse and memorise a set of inter-related work instructions before they are qualified
for active duties and how a Dialectic Soft Systems Model (DSSM) can be as a useful knowledge
acquisition process to acquire the information systematically. The Dialectic Soft Systems Model
(DSSM) progresses through four dialectics: 1st Dialectic - Seek relevant context, 2nd Dialectic Determine the steps of a case study, 3rd Dialectic -Implementation of selected case study and 4th
Dialectic - Test and validate selected case study. Their application of the Dialectic Systems Model
derives a case study for the “12-Car Push-up” operation in a Scenario-based Training System which
serves as an approach in helping new trainees to learn and remember a set of inter-related work
instructions used by a Singapore Railway Service Provider. The “12-Car Push-up” operation is based
on three main points of clarity, involvement and achievement. The Scenario-based Training System
helps to stimulate a trainee’s situational awareness, illustrating context of the situation clearer and more
explicitly by use of multimedia features, promotes andragogical mode of learning and helps a trainee
to overcome the theories of forgetting.
The use of the Dialectic Soft Systems Methodology (DSSM) to construct an organic template
enables the research team to achieve similar desirable outcomes as described in the work of Tay
and Lim (2004). The template helps students solve organic deductive questions in a more systematic
manner and prevent them from forgetting the various chemical tests for different functional groups.
Students can refer to the template and write down the functional groups that might be present in the
compounds given in the question. In this way, students will less likely miss out important information
given in the question.
Besides, Tay and Lim (2007) describes how to apply Dialectic Soft Systems Methodology (DSSM)
as an ongoing self-evaluation process for helping an evaluator or a group of evaluators acquire the
key knowledge about a situation; how to evaluate it against a set of guidelines; how to refine that
assessment; and how to share it with others. Therefore, apart from constructing the template, DSSM
also enables our research team to use it as an ongoing self-evaluation process to refine our templates
against the syllabus, and against any difficulty to be encountered by subsequent batches of students.
The entire cycle of four dialectics is repeated should any major gap be encountered in future. . This
in turn leads the trainee to a deepened appreciation of old answers as often as it leads us to formulate
new ones.
Justifications for adopting a Template Approach
First, template serves as a tool to promote student-directed learning. Katz (1996) reported methods
used to promote student-directed learning at St. Louis College of Pharmacy using alternative approach
to teaching organic chemistry using student-directed learning. The system used enhanced student
ownership, student-active learning, and student accountability and introduced student control to
develop independence and responsibility.
Second, the template serves as a framework of concise summaries of reactions and their properties to empower
a student’s understanding of the common features of diverse functional groups of organic chemistry and allow
him or her to be economical in time management during examinations.The importance of this second aspect is
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highlighted by the research conducted by Goedhart and Duin (1999) on the teaching of structural
formulas in Chemistry. They investigated how upper level secondary school students use the information
that is given by structural formulas, especially with respect to the solubility of compounds in water.
The investigations were based on a small-scale case-study approach, and information was obtained
by recording discussions between students working in small groups. In the first round of the project,
it was concluded that a great deal of students used rules of thumb (like “polar compounds dissolve in
polar solutes”), but their argumentations were not complete and they seemed to lack understanding. A
second round of research tried to provide students with an experiential basis concerning solubility of
organic compounds and let them formulate rules by themselves. Students formulated the rules intended
readily. One of the problems met in the study is that some students did not show a proper understanding
of the “functional group” concept but identified separate element symbols instead.
Third, the template serves as a problem-centered model. Jones (2005) used an active problem-centered
model to teach organic chemistry. In her model, students are responsible for their own first exposure to the
specified material outside the classroom .The preparation includes reading assigned portions of the
text, outlining the material and working on answered examples. The typical class involves a brief
lecture, followed by a general question-and-answer session. Students are then broken into groups to
work on assigned problems. Results have shown that students who adopted the model feel much more
in control of their learning experience and experience less frustration. Active-learning strategies in
organic chemistry seem to work well for students. Our approach using a template hopes to serve as
another learning strategy to help our students in organic chemistry.
Fourth, Bloom’s six of eight domains of intelligence can be deployed as manipulation skills for the
template in order to boost up a student’s confidence in examination. Bloom’s Taxonomy will be used
to classify the problems that our students faced with organic chemistry. Rule and Lord (2003) came up
with a manuscript which contains 13 curriculum units designed to enhance differentiated instruction
for learners with special needs from grades 1-12, including gifted students. It integrates Benjamin
S. Bloom’s levels of cognitive understanding with Howard Gardner’s eight domains of intelligence
to provide a framework for individualized instruction. Each unit has activities for the eight multiple
intelligences (logical-mathematical intelligence, linguistic intelligence, bodily-kinesthetic intelligence,
spatial intelligence, musical intelligence, interpersonal intelligence, intrapersonal intelligence,
and naturalistic intelligence) at each of Bloom’s taxonomic levels: knowledge, comprehension,
application, analysis, synthesis, and evaluation. We utilised six levels in our template: 1) Knowledge:
recalling data or information, 2) Comprehension: understanding the meaning, translation, interpolation,
and interpretation of instructions and problems, 3) Application: using a concept in a new situation or
unprompted use of an abstraction, 4) Analysis: separating material or concepts into component parts so
that its organizational structure may be understood, 5) Synthesis: building a structure or pattern from
diverse elements, putting parts together to form a whole, with emphasis on creating a new meaning
or structure, 6) Evaluation: making judgments about the value of ideas or materials. The six major
categories listed are in order, starting from the simplest behaviour to the most complex. The categories
can be thought of as degrees of difficulties. That is, the first one must be mastered before the next one
can take place. Through surveys and students’ comments, we will be able to identify which categories
our students have difficulties in when answering organic deductive questions
Application of Dialectic Soft Systems Methodology
This section illustrates how this DSSM concept was adopted for the crafting of the organic template (see
Figure 1)
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Immersion from
Reality (Actual
teaching)
4th
Dialectic
Evaluation
of template
1st Dialectic
Finding out and
seeking clarification
3rd Dialectic
Refinement of
template
Final Organic Template
Define the Essence
(summary of
selected practice)
2nd
Dialectic
Derivation
of Template
Partial Organic Template
Figure 1
Target Group
The target groups selected for the study were from the JC 1 cohort. The teaching of organic chemistry
would typically start towards the end of Term 2 and the entire organic syllabus would be completed by
Term 1 of the following year. The template thus had to be designed in stages so that it would cater to
the needs of the students as their lectures progressed.
1st Dialectic: Finding out and seeking clarification
The current system of teaching organic chemistry is based on a lecture-tutorial system. The
students attend lectures for the various homologous series after which they will be given a set of
tutorial questions to prepare for and to discuss with their tutors during tutorials. The lectures for the
entire organic syllabus take up about 17 hours to complete. As for the tutorials, students solve the
questions based on each homologous series to familiarize them with all the reactions and conditions.
Students have a vast number of reactions and conditions to remember over a period of about one and a
half year before they sit for their ‘A’ Level examination. Also they would also have to learn to integrate
across homologous series and to make logical deductions about an unknown organic compound based
on the reactions given. More often than not, students encounter difficulty coping with organic chemistry
in particular in the answering of organic deductive questions.
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A preliminary survey (Appendix 1) was conducted on 111 students who are from 6 tutorial groups to
gauge their level of interest in organic chemistry as well as the problems encountered in the subject.
These tutorial groups comprise students of varying abilities, which are the high ability, average ability
and below average ability. The students were categorized based on their performance in Chemistry
in the Year 1 June Common Test. The students were tasked to solve an organic deductive question
(Appendix 2) prior to responding to the survey. The rationale for this is to enable students to pen down,
if any, the problems encountered while answering the question while it is still fresh in their minds,
thereby making the results collated from the survey more authentic and accurate.
Results of Survey
Based on the survey results (Appendix 3), 66% of respondents agree that they like organic chemistry.
For the listed reasons for liking/disliking organic chemistry, they can be summarized in Table 1.
Reasons for
Chemistry
Liking
Organic Reasons for Disliking Organic Chemistry
Interesting and fun,
Questions are hard
The challenge and thinking involved are Organic structures are hard to deduce
enjoyable
Organic compounds have uses in real life Too many mechanisms/ reactions/ equations/
reagents and conditions to remember
Visual
Reactions and reagents & conditions easy to
confuse and mix up
Answers to organic chemistry questions Same reaction can have multiple reagents &
do not need to be lengthy
conditions
Easier to understand the concepts
Questions usually do not involve
calculations
Table 1: Reasons for Liking and/or Disliking Organic Chemistry
From the reasons stated, it largely is due to them finding the topic interesting and fun or liking the
challenge and thinking involved in the questions. Some students commented that organic chemistry
is relevant to real life (in terms of industrial uses or compounds in daily life) or that it is more visual
(many structures). Some like the fact that it does not involve much calculations and that they do not
need to write as much (compared to questions of other topics) in their answers to usual questions.
However, on the other hand, there were students who found the topic difficult. Some found the questions
hard, but in general, the learning difficulties can be summarized as too much information to memorize
and that it was easy to confuse the reactions of various functional groups. Many commented that if they
understood the topic better, they would enjoy it more.
Based on survey questions 1 and 3, it would appear that most students (66%) like organic chemistry,
and many students (56%) like to solve deductive questions. However, from the results of questions 2,
4 and 5, it seems that most of the students perceive themselves as weak in organic chemistry (78%
disagreed that they are good in organic chemistry), having lack of confidence in the deductive aspect
of the topic (81% disagreed that they are confident in solving deductive questions) and are not swift in
solving deductive questions (85% disagreed that they are quick in solving deductive questions).
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Hence it would appear that a majority of students enjoy the topic of organic chemistry, many of whom
enjoy solving deductive questions, but they do not perceive themselves to be good at it.
A majority of students (72%) agreed that they have problems coping with organic chemistry (Question
6). From the responses of the students across questions 6 and 7(i) to 7(xiv), the problems listed can
be broadly classified using Bloom’s Taxonomy, and the listed reasons can be broadly summarized in
Table 2.
Reasons for having problems coping with organic chemistry
Knowing
the
properties
of
organic
compounds/functional groups
Difficulty in remembering too many
mechanisms, reactions, equations, reagents
and/or conditions
Confusion in various reactions and reagents &
conditions
Difficulty in applying concepts learnt to
larger/more complex molecules
Difficulty in distinguishing between organic
compounds and/or functional groups
Difficulty in making appropriate deductions
Difficulty in piecing information together to
arrive at final structure
Difficulty in linking the concepts from various
topics together
Knowledge (Stage 1)
Knowledge (Stage 1)
Comprehension (Stage 2)
Application (Stage 3)
Analysis (Stage 4)
Analysis (Stage 4)
Synthesis (Stage 5)
Synthesis (Stage 5)
Table 2: Reasons for Having Problems Coping with Organic Chemistry
(Matched to Bloom’s Taxonomy)
Based on the students’ comments, issues such as knowing the properties or organic compounds or
functional groups, and remembering the mechanisms, reactions, equations, reagents and conditions are
all at the lowest level (Knowledge) of Bloom’s Taxonomy. Students may require help in reorganizing
the content of organic chemistry so as to facilitate remembering, which may help in the area of
Comprehension once they are able to discern between various reactions or reagents and conditions.
Likewise students have issues applying the concepts (reactions, reagents and conditions) to more
complex molecules (Application) or within a large organic molecule with multiple functional groups,
students have trouble identifying the functional groups involved (Analysis). This is likely due to
the fact that organic chemistry is taught one homologous series at a time, and students learn each
functional group separately. Hence students need to be assisted in integrating the knowledge across the
homologous series so that they can discern one functional group from another.
Also, students commented that they have difficulties making deductions (Analysis). This is likely due
to the same factor that students are taught one homologous series at a time, and the chemical tests for
each functional group are taught separately and students do not integrate their knowledge across all
topics. Again, helping students reorganize the content into focused themes or sections may be useful.
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The final issue is at the Synthesis level. Students find it hard to use the various piecemeal deductions
and link them together to arrive at a combined structure, or that they cannot see the links across various
homologous series. Hence, it would be useful to provide scaffolds for students that help them integrate
their deductions or knowledge.
Some students mentioned speed in solving questions as a problem, but this problem can be
attributed to familiarity issues (lack of practice) or being bottlenecked at the higher order processes,
hence it was not listed in the table above.
In view of the survey results, it can be concluded that students require assistance in the organization
of the multitude of reactions that are taught in organic chemistry as well as making use of these
reactions to solve organic deductive questions. A template which organizes organic content in a
systematic manner and integrates across homologous series based on the different chemical tests could
be used to solve the problems that students are currently encountering. Moreover by providing a guided
and structured approach, it is hoped that students will be able to acquire the necessary skills for the
answering of deductive questions. Also by using the template, students become more familiar with
the various reactions of organic chemistry and thereby helping students with respect to memorizing
reactions. The template allows students to make quick references for the reactions given in the deductive
question and indirectly helps in time management for the answering of question as well.
2nd Dialectic: Derivation of Template
The first version of the template (Appendix 4) was designed for the topics of hydrocarbons, alcohols,
carbonyl compounds and carboxylic acids, both aliphatic and aromatic. This was a partial template
which did not include all the homologous series in organic chemistry as the students involved in the
study had not been taught the entire organic syllabus yet. The template is in the form of a table to
enable students to make quick references based on the information given in the deductive question.
The template is divided into a number of stages. The first stage covers general deductions about the
unknown organic compounds based on their physical properties such as physical state or solubility. In
the answering of deductive questions, it is logical to make deductions based on their physical properties
before any further deduction is made based on the chemical reactions given. The second stage covers
the specific deductions about the compound which are the chemical tests for the various functional
groups. As students are taught organic chemistry by homologous series, more often than not they do
not see that a particular chemical test could be used to test for a number of functional groups. This stage
is thus a compilation of all the chemical tests and the various functional groups the tests are affiliated to
in the organic syllabus. A three-column table is constructed to allow students to make quick references
to the information given and to make their deductions in a guided manner. The last column in the table
for the first two sections is written in such a way to allow students to transfer the deductions straight
into their written answers. Stage 3 of the template focuses on helping students to construct the organic
structure based on the products deduced.
3rd Dialectic: Refinement of Template
A trial run for the partial template was implemented, with 60 students from 3 tutorial groups
participating, again of varying abilities. During this trial, students were taught during tutorial
sessions on how to use the template for the answering of organic deductive questions. A
sample question (Appendix 5) was discussed with tutors illustrating how the template should
be used. Students were then tasked with solving an organic deductive question (Appendix
6) on their own and to write down the problems encountered immediately on the working
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sheet (Appendix 7) provided. This would enable us to capture the problem areas that the template had
failed to address.
Analysis of problems encountered extracted from working sheet
The analysis of the problems that students encountered while using the template and the corresponding
action that was taken to refine the template can be summarized in Table 3.
Problems encountered by student with Refinements made to template
accompanying quotes.
“unclear what deductions could be made Insolubility in water was inserted under the
from insoluble in water and soluble in general deductions in stage 1.
NaOH(aq)”
Also examples of common bases used in
organic reactions are listed down.
“cannot find NaOH as reagent”
Reagent was inserted into stage 2 of the
This particular reagent was left out template.
inadvertently.
“not sure how to explain reactions of G”
The type of reaction and also the mechanism
Students were unable to explain reactions that were inserted into the ‘functional group’
are taking place for each of the chemical tests column and the term ‘deduction’ was added
listed in stage 2 of the template.
to the Heading.
It was noted that the template was also not Negative tests were inserted into the template
consistent in the area of presentation. For to make it more consistent and also to train
stage 2, some tests had negative test students that deductions could be made from
incorporated while others did not. Though it tests which are negative.
was possible for students to make deductions
about negative tests based on the positive
tests given, this was not the case in the
answers from some of the students. It was
noted that students made deductions for those
tests which are negative only when it was
shown in the template eg. Fehling’s Test.
“Don’t know how to arrive to the structure Stage 3 of the template helps students to link
using the deductions”
information together to a certain extent.
However the derivation of the final structure
of an organic compound from the various
deductions made is a higher order skill which
require practice and as such cannot be
addressed by the template.
Table 3: Problems that Students Encountered with the Template, and Corresponding Refinements
4th Dialectic: Evaluation of Template
The final version of the template (Appendix 8) which covers the entire organic syllabus was
constructed after the 3rd Dialectic. The template was implemented on 60 students who were
tasked with answering one deductive question (Appendix 9). As what was done during the trial for
the partial template, students had to record the problems encountered in the working sheet. In addition
a survey (Appendix 10) was administered to get their feedback on the use of the template for the
answering of organic deductive questions.
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Results and Analysis of Survey
Analysis of the survey (Appendix 11) showed that more than 80% of the students know how to use the
template and they also found it useful. About the same percentage of the students surveyed felt that the
template increases their confidence in solving organic deductive questions. 90% felt that the template
provided them with a quick reference for the various chemical tests and reactions.
From Question 10 of the survey, “What do you like about this template?”, the responses can be
categorized in the table below. For the listed reasons (note that a respondent can list more than one
reason) for liking the template, they can be grouped and summarized in Table 4.
Reasons for
template
liking
the Category
Organized, concise, easy to
read, good summary, easy to
memorize, comprehensive
Easy to use / refer to / identify /
deduce, has useful information,
know where to start
Allows for quick reference,
helps solve the question quickly
Teaches to use step by step,
breaks process into stages
Number of respondents
(Total 47) with such
responses
Organization, details and 34 (72.3 %)
presentation
Ease of usage and 16 (34.0 %)
application to question
Improving students’ speed 4 (8.5 %)
at solving
Systematic scaffolding
3 (6.4 %)
Table 4: Reasons for Liking the Organic Chemistry Template
About 72.3 % of the respondents indicated in their responses that they like the organization (good
summary of all the reactions), amount of details and comprehensiveness, concise nature which aids in
memorization. 34 % of the respondents indicated liking the ease of use and how it is useful in helping
them solve a deductive question. 8.5 % mentioned it helps them solve the question at a faster speed,
and 6.4 % indicated that it helps them to approach the question step by step.
As for Question 11 of the survey, “What do you not like about this template?”, the listed reasons
(note that a respondent can list more than one reason) for liking the template, they can be grouped and
summarized in Table 5.
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Reasons for not liking the Category
template
Number of
(Total 47)
responses
Missing Information, details, Content
deductions / reactions and/or
equations
Template is not well-organized Organization
and
presentation
Difficulty in usage, or that the Ease of usage and
template was not helpful and/or application to question
applicable to question
Flipping through the template Improving
students’
takes time
speed at solving
The template doesn’t help Systematic scaffolding
enough in linking information
together
No response
27 (57.4 %)
respondents
with such
1 (2.1 %)
3 (6.4 %)
2 (4.3 %)
1 (2.1 %)
14 (29.8 %)
Table 5: Reasons for Not Liking the Organic Chemistry Template
About 57.4 % of the respondents indicated in their responses that they feel that some reactions, details,
information, reactions are missing still. 2.1 % mentioned that it’s not well-organized. 6.4 % indicated
that they still didn’t know how to use the template or that it wasn’t helpful. 4.3 % indicated that flipping
takes time, and 2.1 % felt that the template didn’t help them piece together the information. 29.8 %
of respondents left this field blank (1 respondent wrote that he/she loves the template), which may
suggest that they like the template, and the responses from the other questions seemed to corroborate
this. This is a positive point to note.
Based on the responses on Q10 and 11, an observation can be made – although many respondents
mentioned that they found the template a good summary or comprehensive, almost all of these
respondents also commented that there was missing information. So while the template lists most of
the common reactions, these respondents wanted an absolutely complete list of reactions.
While 92% of the students surveyed (Appendix 10) felt that the template provided guidance on how
to start answering the deductive question, only about 70% felt that it helped them piece information
together and also in the final derivation of the structure.
From Question 12, of the survey, “What are the problems encountered when using the template?”, the
listed problems in using the template (note that a respondent can list more than one problem), they can
be grouped and summarized in Table 6.
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Problems encountered Category
when using the template
Number of
(Total
47)
responses
Missing Information, details
,deductions/reactions, and/or
equations
Template is hard to read
and/or messy
Students had not revised
fully, they were unfamiliar
with template, found the
template hard to use or
confusing, or that they did
not use the template at all
Difficulty
in
making
deductions and/or linking
information together
No response / no problem
10 (21.3 %)
Content
respondents
with
such
Organization
and 2 (4.3 %)
presentation
Ease of usage and 13 (27.7 %)
application to question
Systematic scaffolding
5 (10.6 %)
17 (36.2 %)
Table 6: Problems Encountered when Using the Template
About 21.3 % mentioned the point about missing information. However, note that these 10 respondents
have already mentioned the same problem for Q11, so they are a subset of the 27 respondents for Q11. 4.3
% mentioned that they didn’t like the presentation of the template. 27.7 % mentioned something to the
effect of finding the template difficult to use. Note that the 3 respondents who commented similarly for
Q11 also fall within this 27.7 %. 10.6 % of respondents mentioned that the template didn’t help them
arrive at the final structure. However, only 2.1 % of respondents that made a similar comment does not
fall within this group. Hence, the total should be considered as 12.7 % for this aspect across Q11 and
12. It is thus encouraging to note that 36.2 % had no problems using the template at all.
The responses to Question 13 of the survey, “Some suggestions for improvement?” can be grouped and
summarized in Table 7.
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Suggestions for Improvement
Category
Include
more
information,
details, reactions, reagents,
equations
Group reactions for specific
compounds together, be more
organized, use diagrams, and/or
draw structures
Show examples of more
questions
Content
Organization
presentation
Number of
(Total 47)
responses
15 (31.9 %)
respondents
with such
and 4 (8.5 %)
Ease of usage and 1 (2.1 %)
application
to
question
Demonstrate how to piece Systematic
1 (2.1 %)
together the final structure
scaffolding
Do not use template again
2 (4.3 %)
No response or that the template
21 (44.7 %)
is good enough
Table 7: Suggestions for Improvement for the Organic Template
31.9 % requested to include more reactions. 8.5 % suggested better organization, e.g. grouping some
reactions together, using diagrams to organize the information, or provide drawings of structures. 2.1
% suggested using more questions as examples. Another 2.1 % suggested more details on how to piece
together the final structure. 4.3 % requested not to use the template again. However, 44.7 % had no
response, so it is inconclusive if the students wanted to but had no ideas for improving the template, or
that they found that it did not need improving (only 1 respondent commented this).
Analysis of problems encountered extracted from working sheet
The problems encountered by the students while using the final version of the template were summarized
in Table 8.
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Analysis of problems encountered extracted from working sheet
The problems encountered by the students while using the final version of the template were
summarized in Table 8.
Problems encountered by student with Refinements made to template
accompanying quotes.
“What
does
the
reagent
sodium
hydrogencarbonate mean?”
“What is sodium hydrogencarbonate? I only
know sodium carbonate.”
Students did not realize that the tests sodium
hydrogencarbonate and sodium carbonate
serve the same purpose.
“How to get two =CH2 so that two moles of
CO2 is given off?”
Students failed to see that while a terminal
double bond on oxidation liberates one mole
of CO2, there could be another reaction
involved that could contribute to the second
mole of CO2 evolved. This observation
surfaces one disadvantage of the use of
template. It appeared that students were
following the template blindly and they were
not doing their own independent analysis.
Their thought processes were restricted along
the direction as guided by the template.
“How to deduce which functional group to
choose.”
It was noted that students were able to state
the functional groups present as given by the
template. However there were some who had
problems linking the information together
and through systematic elimination arrive at
the final structure of the unknown organic
compound.
“No NaCN and HCN in template. Don’t
know what to deduce.”
These reagents do not fall under the category
of chemical tests.
The reagent sodium hydrgencarbonate is
incorporated into the template.
The purpose of the template is just to provide
students with the scaffolding for the
answering of organic deductive questions.
Higher order skills which involve reasoning
and systematic analysis could not be
addressed by the use of the template.
The template is meant to help students arrive
at the functional groups present. However,
the linking of the information deduced again
is a higher order skill which cannot be
addressed by the template.
The template is not meant to be a compilation
of all the possible reactions in organic
chemistry.
Table 8: Problems Encountered by Students Recorded in Students’ Working Sheets,
Analysis and Subsequent Refinements
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Conclusion
The use of Dialectic Soft Systems Methodology (DSSM) has allowed the construction of a viable and
workable template to assist students in answering deductive questions in organic chemistry at the A
Levels.
Using the DSSM, the attitudes and views of the students towards organic chemistry as well as the
problems they faced when solving deductive questions (1st Dialectic) was first explored and analysed.
The data was then used to construct a template to address the difficulties students faced when solving
deductive questions (2nd Dialectic). The template contained information pertaining to common physical
properties and tests commonly seen in deductive questions as well as the deductions that can be made
from the properties or tests. It was designed in a table form so that students would be able to make
quick references to the information contained and to make their deductions in a logical manner. The
template was then refined by conducting a trial where a sample of students were allowed to use the
template to solve a deductive question in organic chemistry and asked to comment on the problems or
difficulties they encountered when using the template (3rd Dialectic). The comments were analysed
and changes were made to template to address the problems students faced. The final version of the
template was then evaluated by again allowing students to use the template to solve another deductive
question in organic chemistry and comment on any problems of difficulties faced (4th Dialectic). In
addition, a survey was also administered to obtain feedback on the use of the template for answering
organic deductive questions. It was found that students were generally positive about the template and
felt that it did help them to get started on answering the organic deductive question and piecing the
information together. However, a fair number also indicated that the template was missing some
reactions, details, information and reactions. From the analysis of the data, the template was then
further refined again (3rd Dialectic).
Not only has the use of the Dialectic Soft Systems Methodology (DSSM) assisted in the construction
of the template for students to solve organic deductive questions, it also allows the continual review
and refinement of the template created over time, making each version more user friendly and
comprehensive for subsequent batches of students that will be provided with the template. As such,
this methodology can be applied by teachers or educators in other areas and subjects. The educator
can first construct a survey to find out the attitudes, perceptions and problems students face when
tackling a particular subject or topic (1st Dialectic). New methods of pedagogies or learning tools used
to tackle the problem and aid students in learning can then be constructed based on the data obtained
(2nd Dialectic). The pedagogical method or learning tool would then provided to the students and
feedback obtained from them. Based on the feedback, the method or tool could be further refined
and tested again with either the same students or with subsequent batches of students (3rd and 4th
Dialectic). With each testing and feedback, previously unseen problems, inadequacies or limitations
of the pedagogical method or learning tool would be revealed, allowing the educator to further refine
it to address the new problems revealed over time. The Dialectic Soft Systems Methodology (DSSM)
can also be used to construct educational programmes for students such as remedial or enrichment
programmes and refine these programmes over time. One advantage of the Dialectic Soft Systems
Methodology (DSSM) is hat it allows the pedagogical methodology or learning tool or programme to
continually change and adjust to target the needs of different batches students which may gradually
change over time. Another advantage of the Methodology is that it allows the educator to use it within
the course of his work. The educator or group of educators can obtain feedback from the students they
teach and construct various new pedagogical methods and learning tools to use. Further feedback can
be obtained on the students to continually refine and improve the creation and allow it to adjust to
students changing needs over time.
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The template created can also be provided to the next batch of students to aid them in their learning of
organic chemistry and the solving of deductive questions. Although the template has generally been
found by students to be helpful in their learning and solving of organic deductive questions, there
are still a few limitations of the template. Firstly, the template does not contain every single possible
organic reaction. This is because the table is designed to be quickly referenced by the user. If every
possible detail or organic reaction were included in the template, the amount of information would
simply be too vast for students to effectively sieve through in a short period of time. Hence, only the
common physical properties and tests seen in A Level organic deductive questions were selected and
included in the template. Already, this has caused the template to span 5 full pages, causing some
students to comment that valuable time was wasted in “flipping the pages” to look for the information.
The second limitation of the template is that although it enables students to quickly reference and
deduce the various functional groups of the organic molecule given the information in the deductive
question, it does not address the higher order skills required to completely solve the deductive question,
for example to link the various functional groups together to obtain the final unknown molecule. The
reason for this is that the template was designed with the aim of providing students with the scaffolding
for the answering or organic deductive questions. It helps them organize the vast amount information
they have learnt from the various homologous series in organic chemistry and apply it in a systematic
manner to identify the various functional groups in an unknown organic molecule given the various tests
and properties in a typical A Level organic deductive question. In addition, most of the marks awarded
in a typical deductive question is allocated to the identifying of the various unknown functional groups
in the unknown molecule. Hence, the template, if correctly used, would allow the student to score most
of the marks in a typical deductive question.
The next stage of the research could be to gather more data on the effectiveness of the template as
opposed to the conventional way of teaching. It would be interesting to find out if the students using the
template can actually grasp the methods used in the solving of organic deductive questions more quickly
then if the conventional method was used. It would also be important to verify if the use of the template
allows the students to obtain better scores when answering deductive questions. Most importantly, it
would be useful to verify if students using the template are able to master the solving techniques and
remember the information such that they are able to solve deductive questions without the use of the
template or if they become too reliant on the template. Another way possible direction the research can
proceed is to continue using the Dialectic Soft Systems Methodology (DSSM) to redesign the template
such that it aids the students in the higher order skills like piecing the various functional groups together
to form the unknown molecule. In fact, if further research is carried out to test theeffectiveness of the
template, the Dialectic Soft Systems Methodology (DSSM) can still be used to refine and improve the
template as feedback is obtained from the students.
It is desirable that the template derived from this piece of research will be useful to students in their study
of organic chemistry. But more than that, it is projected that through this research, various educators
will see the benefit and usefulness of the Dialectic Soft Systems Methodology (DSSM) and embark on
their own research in their own respective areas using the Methodology which would certainly improve
the education landscape in time to come.
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References
Goedhart, M. and Duin, Y. (1999), Teaching Structural Formulas in Chemistry: How Students Relate
Structural Formulas to the Solubility of Substances. Annual Meeting of the National Association for
Research in Science Teaching (Boston, MA, Mar 28-21).
Jones, T.M.W. (2005). Teaching problem-solving skills without sacrificing course content. Journal of
College Science Teaching 35, No.1 (S 2005), 42-46.
Katz, M. (1996), Teaching organic chemistry via student-directed learning: a technique that promotes
independence and responsibility in the student. Journal of Chemistry Education 73, no. 5 (May 1996),
440-445.
Rule, A.C. and Lord L.H. (2003), Activities for Differentiated Instruction Addressing All Levels of
Bloom’s Taxonomy and Eight Multiple Intelligences. State University of New York at Oswego, Collected
Works, Teachers (052).
Tay, B. H. and Lim, K. P. (2004), A Scenario-based Training System for a Railway Service Provider
in Singapore. Proceedings, Systems Engineering/ Test and Evaluation Conference 2004 in Adelaide,
Australia.
Tay, B. H. and Lim, K. P. (2007), Using Dialectic Soft Systems methodology as an Ongoing Selfevaluation Process for a Singapore railway Service Provider in Systems Concepts in Evaluation , an
Expert Anthology. Williams, B. and Iman, R. (eds), pp89 – 100. American Evaluation Association.
California: Edge Press of Inverness.
Winter, A. (2005). Organic chemistry I for dummies. New Jersey: Wiley Publishing, Inc.
Website: Learning Domains or Bloom’s Taxonomy:
http://www.nwlink.com/~Donclark/hrd/bloom.html
Website: Major Categories in the Taxonomy of Educational Objectives (Bloom 1956):
http://krummefamily.org/guides/bloom.html
Acknowledgements
We are indebted to colleagues and students for the ideas expressed in this paper. We are very much
indebted to Dr Tay Boon Hou and Dr Eric Goh for their invaluable guidance throughout our research.
We are also grateful to Research@Eastzone for the support in terms of the facilities and data base
resources.
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Appendix 1
Survey Questions
Please rate how strongly you agree or disagree with each of the following statements by shading the
appropriate circles
1
I like Organic Chemistry.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
Reasons:
____________________________________________________________________________
____________________________________________________________________________
2
I am good in Organic Chemistry.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
3
I enjoy solving deductive questions.
Disagree
4
I am confident in solving deductive
questions.
Disagree
5
I am quick in solving deductive
questions.
Disagree
6
I have problems coping with Organic
Chemistry.
Disagree
List down the problems you faced:
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
7
I find solving deductive questions a
tedious chore.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
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Possible reasons are:
(i)
When I see a deductive question, I
usually do not know where to start.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
Reasons why you know/ do not know where to start:
_____________________________________________________________________
_____________________________________________________________________
_____________________________________________________________________
(ii)
I can easily recall the reactions of
various functional groups.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
(iii)
I can easily recall the reagents and
conditions of chemical tests I have
learnt.
Disagree
(iv)
I know the relevant chemical tests to
distinguish
between
various
functional groups.
Disagree
(v)
I can easily write balanced equations
for various reactions.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
(vi)
(vii)
I can recall reagents and conditions
but I am confused about what
functional groups they are used to test
for.
I have difficulty remembering the
various chemical tests.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
Disagree
(viii)
(ix)
I am usually able to think of various
possible functional groups by
analyzing the given molecular
formula(e).
I am usually able to pick out relevant
information
from
deductive
questions.
Disagree
Disagree
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(x)
I am usually able to make deductions
based on the information gathered.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
(xi)
I am usually able to see links between
the multiple deductions made.
Disagree
(xii)
I am usually able to arrive at a final
structure.
Disagree
(xiii)
I usually do not know how to use the
deductions made to deduce the final
answer.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
(xiv)
I find problems phrasing
presenting my answers.
and
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
Others:
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
Thank you for your time!
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Appendix 2
Compound L, C8H16O2, decolourises aqueous bromine from brown to a colourless solution at
room temperature. L reacts with I2 in aqueous NaOH under heating to give a yellow
precipitate, and reacts with solid PCl5 in the cold to liberate white fumes. One mole of L
reacts completely with sodium metal to liberate one mole of hydrogen gas.
Oxidation of L using acidified KMnO4 under reflux produces only one organic product, M
with a molecular formula C4H6O3.
Compound M liberates carbon dioxide gas when it reacts with solid Na2CO3.
Deduce the structures of L and M, and explain your reasoning clearly, including relevant
balanced equations.
Sample Answer:
•
From the molecular formula of L (C8H16O2), it can be observed that the carbon to
hydrogen ratio is low thus implying that L may be an aliphatic compound (i.e. absence of
benzene ring)
•
The molecular formula of L shows the presence of 2 oxygen atoms. This implies that L
may contain either 2 –OH groups, 1 –COOH group, 1 –OH group and R–C–H or 1 –OH
group and 1 R–C–R’.
O
O
•
The decolourisation of aqueous bromine when it is added to L indicates the presence of
carbon-carbon double bond.
•
A positive iodoform test which resulted in the formation of a yellow ppt (CHI3) implies
that the following structures are present in L:
OH
H3C
C
O
Or
H3C
C
Where
:R
H
•
White fumes of HCl are observed when PCl5 is added to L. This implies the presence of –
OH groups in L.
•
Since 1 mol of compound with 1 –OH group present will give ½ mol of hydrogen gas and
1 mol of L gives 1 mol of hydrogen gas, this implies that there are 2 –OH groups present
in L.
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•
L undergoes strong oxidation with acidified KMnO4 to give only 1 organic product, M.
Since –OH groups are present in L, L may be a primary or secondary alcohol (tertiary
alcohols do not undergo oxidation). It may also imply the oxidation of carbon-carbon
double bond which is present. Since only 1 organic product is obtained, this implies that
L is a symmetrical alkene. The number of carbon atoms in L is twice the number of
carbon atoms in M, indicating that the cleavage of carbon-carbon double bond in L would
give 2 moles of M.
•
M can react with Na2CO3 to liberate CO2 gas, this implies that M contains the –COOH
group.
•
From the molecular formula of M (C4H6O3), it can be seen that there are 3 oxygen atoms.
Thus it can be deduced that 2 of the oxygen atoms belong to the –COOH group and the
last oxygen atom belongs to a ketone group which is obtained from the oxidation of a
secondary alcohol.
•
Thus L is
OH
H3C
C
CH2
H
H
C
C
OH
CH2
H
•
C
CH3
H
M is
O
H 3C
C
OH
CH2
C
O
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Appendix 3
1. I like Organic Chemistry.
3% 7%
18%
Strongly Disagree
8%
Disagree
19%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
45%
2. I am good in Organic Chemistry.
2%
0%
19%
20%
Strongly Disagree
Disagree
14%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
45%
3. I enjoy solving deductive questions.
13%
2%
9%
Strongly Disagree
14%
Disagree
Somew hat Disagree
Somew hat Agree
41%
21%
Agree
Strongly Agree
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4. I am confident in solving deductive questions.
3%
0%
16%
Strongly Disagree
30%
Disagree
Somew hat Disagree
Somew hat Agree
Agree
36%
Strongly Agree
15%
5. I am quick in solving deductive questions.
11%
1%
3%
Strongly Disagree
Disagree
38%
Somew hat Disagree
Somew hat Agree
31%
Agree
Strongly Agree
16%
6. I have problems coping with Organic Chemistry.
10% 2% 7%
Strongly Disagree
19%
22%
Disagree
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
40%
7. I find solving deductive questions a tedious chore.
8%
5%
12%
19%
Strongly Disagree
Disagree
17%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
39%
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7(i) When I see a deductive question, I usually do not know where to start.
6% 4%
12%
Strongly Disagree
21%
Disagree
Somew hat Disagree
Somew hat Agree
27%
Agree
Strongly Agree
30%
(ii) I can easily recall the reactions of various functional groups.
0%
4%
15%
Strongly Disagree
22%
Disagree
Somew hat Disagree
17%
Somew hat Agree
Agree
Strongly Agree
42%
(iii) I can easily recall the reagents and conditions of chemical tests I have learnt.
1%
23%
0%
20%
Strongly Disagree
Disagree
Somew hat Disagree
18%
Somew hat Agree
Agree
Strongly Agree
38%
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(iv) I know the relevant chemical tests to distinguish between various functional groups.
0%
9%
5%
Strongly Disagree
15%
Disagree
Somew hat Disagree
Somew hat Agree
52%
Agree
19%
Strongly Agree
(v) I can easily write balanced equations for various reactions.
14%
1%
9%
Strongly Disagree
16%
Disagree
Somew hat Disagree
Somew hat Agree
Agree
35%
Strongly Agree
25%
(vi) I can recall reagents and conditions but I am confused about what functional groups they
are used to test for.
8%
5%
9%
Strongly Disagree
17%
Disagree
Somew hat Disagree
21%
Somew hat Agree
Agree
Strongly Agree
40%
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(vii) I have difficulty remembering the various chemical tests.
15%
2% 5%
Strongly Disagree
15%
Disagree
Somew hat Disagree
Somew hat Agree
25%
Agree
Strongly Agree
38%
(viii) I am usually able to think of various possible functional groups by analyzing the given
molecular formula(e).
2%
20%
5%
7%
Strongly Disagree
Disagree
15%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
51%
(ix) I am usually able to pick out relevant information from deductive questions.
4%
3% 4%
12%
Strongly Disagree
Disagree
31%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
46%
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(x) I am usually able to make deductions based on the information gathered.
15%
4% 5%
11%
Strongly Disagree
Disagree
13%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
52%
(xi) I am usually able to see links between the multiple deductions made.
14%
2% 8%
12%
Strongly Disagree
Disagree
Somew hat Disagree
Somew hat Agree
27%
37%
Agree
Strongly Agree
(xii) I am usually able to arrive at a final structure.
8% 0%
11%
Strongly Disagree
19%
28%
Disagree
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
34%
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(xiii) I usually do not know how to use the deductions made to deduce the final answer.
6% 4%
17%
16%
Strongly Disagree
Disagree
Somew hat Disagree
Somew hat Agree
22%
Agree
Strongly Agree
35%
(xiv) I find problems phrasing and presenting my answers.
19%
1%
12%
Strongly Disagree
Disagree
18%
Somew hat Disagree
Somew hat Agree
21%
Agree
29%
Strongly Agree
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Appendix 4
Initial Deductive
Stage 1 (General Deductions)
1.
Properties
C: H ratio
High
2.
Soluble in
Low
Base
Water
3.
Physical state
4.
Formula
Solid
Gas
1 oxygen atom
2 oxygen atoms
Deductions
Highly
unsaturated.
Aromatic
Aliphatic
Acidic
in
nature
Able to form
hydrogen
bonds
with
water
molecules
High mp
Very low bp
Possible functional groups
Presence of benzene ring
Absence of benzene ring
Phenol, -CO2H
-OH, -CO2H group present
High Mr
Low Mr
-OH
Two -OH groups, -CO2H
Stage 2 (Specific Deductions)
Reagents
Conditions
Na (s)
and Observations
Functional groups
H2 Ĺ
No H2 Ĺ
-OH group
No - OH group
Brady’s reagent
Orange ppt
2,4dinitrophenylhydrazine
Carbonyl compound
RCHO or
ketone, RCR’ present
eg
aldehyde,
O
Absence of carbonyl compounds
No orange ppt
Reagents
and Observations
Conditions
Reddish-brown ppt
Fehling’s
Alkaline solution of
Cu2+ tartrate, heat
Functional groups
Organic compound easily oxidized.
Presence
of
aldehyde
except
benzaldehyde
No reddish-brown ppt
Absence of aliphatic aldehyde
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Tollen’s
Ammonical
nitrate, heat
Silver mirror
Organic compound easily oxidized.
Presence of aldehydes
No silver mirror
Yellow ppt
Absence of aldehyde
silver(I)
Iodoform test
Alkaline aq. Iodine/
heat
OH
Presence of CH3C
R
H
Where R : H, alkyl or benzene ring
No yellow ppt
OH
Absence of CH3C
R
H
Where R : H, alkyl or benzene ring
Br2/CCl4
Br2(aq)
PCl5 or SOCl2
Na2CO3
Neutral FeCl3
Decolourisation
Compound unsaturated, C=C present
No decolourisation
Absence of C=C
Decolourisation with white ppt
-OH group attached directly to benzene
ring eg. phenolic group
Decolourisation
Presence of C=C
White fumes of HCl
Presence of -OH except phenol
No white fumes
Absence of –OH
Effervescence of CO2
Sample acidic, presence of -CO2H
No effervescence
Sample not acidic, absence of -CO2H
Violet complex
Phenolic group present
i.e. -OH group attached directly to
benzene ring
Compound can be oxidized e.g. could be
primary or secondary alcohol
Acidified K2Cr2O7 or Orange dichromate turned green
or
KMnO4, heat
Decolourisation
of
acidified
KMnO4
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Stage 3 (Linking Information Together)
Reaction
Oxidation
KMnO4, acidified, reflux
Observations
[ O]
Alkene X Æ Y + CO2
Less C atoms in Y
effervescence (CO2 evolved)
Alkene X
Deductions
Terminal alkene, RC=CH2
or
[ O]
Æ Y
R’
Where R, R’ = H or alkyl group
Symmetrical alkene, RC=CR
R’ R’
Number of C atoms in Y is half of
the number of C atoms in X
Alkene X
[ O]
Æ Y + Z
Both Y and Z are ketones
Unsymmetrical alkene
Y & Z are ketones or carboxylic
acids
(Piece information together to
determine position of double
bond)
RC=CR’
R’’R’’’ where R, R’, R’’ R’’’
are alkyl groups
Both Y and Z are carboxylic RC=CR’
acids
H H
Y is ketone and Z is carboxylic RC=CR’
acid
R H
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Alkene X
[ O]
Æ
Y
Same number of C atoms in X and Cyclic alkene with one double
bond.
Y
Reaction
Observations
Deductions
Removal of H2O molecule from
Dehydration
H
H
Al2O3,
heat
or
excess alcohol to form alkene
concentrated H2SO4, 180 °C
C
R
C
H
H
C
OH
H H
R-C=C-CH2R’
R’
H
H H
RCH2C=CR’
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Appendix 5
4.
Alcohol B forms esters, which are responsible for the flavours of various fruits and has
the molecular formula C5H12O. Reaction of B with acidified potassium dichromate (VI)
produces a compound C, C5H10O2. Heating B over Al2O3 produces D, C5H10. Vigorous
oxidation of D forms 2-methylpropanoic acid as one of the products.
Suggest structures for B, C and D and explain the reactions involved.
[5]
J94 / I / 10(b)
Explanation:
ƒ B Æ C: Alcohol B is oxidised to C. From the molecular formula of B and C, B is a
primary alcohol (contains –CH2OH group) and C is a carboxylic acid.
ƒ B Æ D: Since B contains -CH2OH, dehydration gives only one alkene (D) and D is a
terminal alkene.
ƒ On vigorous oxidation, D (containing 5 carbon atoms) forms 2-methylpropanoic acid
(containing 4 carbon atoms). Total bond cleavage has taken place during strong
oxidation to give 2-methylpropanoic acid and CO2 as D is a terminal alkene.
2-methylpropanoic acid
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Compound
Structure
CH3-CH-CH2-CH2-OH
|
CH3
B
C
CH3-CH-CH2-CO2H
|
CH3
D
CH3-CH-CH=CH2
|
CH3
Appendix 6
Appendix 6
* Supplementary Questions (the question which students did on the documenting
sheet)
1.
The compound 4-ethylphenol, E, and chlorinated products derived from it have useful
antiseptic properties.
CH3CH2
OH
OH
E
Depending on the conditions of the reaction, compound E can react with chlorine in
two different ways, giving the two isomers F and G. In these reactions chlorine reacts
in a similar manner to bromine.
I
C8H8Cl2O
F
(a)
II
E
C8H8Cl2O
G
Cl2(aq)
(i) Suggest a structural formula for compound F.
Cl
OH
CH3CH2
Cl
(ii) Explain whether you would expect F to be more or less acidic than phenol.
•
•
More acidic than phenol.
Two electron-withdrawing Cl atoms stabilises the anion by enhancing the
dispersal of negative charge into the benzene ring, making proton leaving
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easier.
(b)
Compound G reacts with NaOH (aq) to give H, C8H10O3, which immediately loses
water to give J, C8H8O2. Compound J is insoluble in water but it dissolves in
NaOH(aq). It reacts with 2, 4-dinitrophenylhydrazine and with alkaline aqueous iodine,
but not with Fehling’s solution.
(i) Identify and draw the structural formulae of compounds G, H and J. Explain the
reactions described and write equations where appropriate.
Cl
G:
OH
C
CH3
H:
OH
CH3
Cl
OH
C
OH
J:
C
CH3
OH
O
On reaction with aq. NaOH, nucleophilic substitution occurs:
Cl
CH3
OH
OH + 2 OH Æ CH3
C
OH + 2 Cl
C
Cl
OH
G
H
Since the two hydroxyl groups are on the same carbon atom, H immediately loses
water to give J.
OH
CH3
OH
C
CH3
Æ
OH
+
C
O
OH
H2O
J
H
J is a ketone with a carbonyl functional group and reacts with 2,4dinitrophenylhydrazine to give an orange ppt of 2,4-dinitrophenylhydrazone.
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HO
HO
H2NNH
NO2
C
O
C
+
NNH
NO2
CH3
CH3
+ H2O
NO2
NO2
J has the CH3-C=O functional group and reacts with alkaline aq. iodine to give
CHI3.
(ii) Suggest suitable conditions for reaction II.
Cl2(g), room temperature, in the presence of UV light.
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Problems
Encountered
Problems
Encountered
Working sheet for documenting
Appendix 7
Structure C
Structure A
Structure D
Structure B
Problems
Encountered
Problems
Encountered
Appendix 8
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Appendix 9
The compounds P and Q are isomers with the molecular formula C9H8O2.
P liberates carbon dioxide with sodium hydrogencarbonate but Q does not.
Upon reaction with hot acidified potassium manganate (VII), 1 mole of P gives 2 moles of
carbon dioxide and C7H6O2 while 1 mole of Q gives 1 mole of carbon dioxide and C8H6O3.
P decolourises aqueous bromine in the dark to form R, C9H9O3Br. Q reacts with aqueous
bromine to form white precipitate of S, C9H6O3Br3.
Q can be obtained by reacting T, C9H10O3, with excess concentrated sulphuric acid at 170°C.
T gives a yellow precipitate on reaction with aqueous alkaline iodine solution.
When Q reacts with a mixture of NaCN and HCN, U is produced.
Suggest the structures of P, Q, R, S, T and U, explaining the chemistry of the reactions
described.
Answers
Ÿ P and Q contains benzene ring
P undergoes neutralization with sodium hydrogencarbonate.
Ÿ P is a carboxylic acid
P undergoes oxidation with hot acidified KMnO4 to form product with 2 carbon atoms less.
Ÿ P is an alkene
Q undergoes oxidation with hot acidified KMnO4 to liberate CO2.
Ÿ Q is a terminal alkene
P undergoes electrophilic addition with aqueous Br2 in the dark
Ÿ P is an alkene
Q undergoes electrophilic substitution with aqueous Br2
Ÿ Q is a phenol
T undergoes elimination with excess concentrated H2SO4 to form Q
Ÿ T is an alcohol
T undergoes oxidation with alkaline iodine
CH3
C
Ÿ T contains
OH
H
Q undergoes nucleophilic addition with a mixture of NaCN and HCN to from U.
Ÿ Q is carbonyl compound
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OH
H
C
C
C
CN
H
H
U
O
OH
C
C
T
CH 3
H
HO
HO
Excess conc
H2SO4, 170°C
HCN/NaCN
O
H
C
H
H
O
C
C
C
OH
C
C
H
H
HO
Q
OR
OH
P
O
C
Br2 (aq)
Br2 (aq)
H
C
C
H
H
O
H
H
C
C
C
OH
Br
O
H
H
C
C
C
Br
OH
S
H
H
O
C
C
C
OH
Br
Br
H
R
OH
HO
Br
OR
OR
H
H
O
C
C
C
Br
OH
Br
OH
H
HO
Br
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Appendix 10
Survey Questions
Please rate how strongly you agree or disagree with each of the following statements by
shading the appropriate circles.
1
The template is useful.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
2
I know how to use the template.
Disagree
3
The template increases my confidence
in solving deductive questions.
Disagree
4
The template helps me to solve
deductive questions at a faster speed.
Disagree
5
The template helps me solve deductive
questions.
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
O
O
O
O
O
O
Strongly
Disagree
Disagree
Somewhat
Somewhat
Agree
Agree
Strongly
Agree
Disagree
6
I know where to start when I see a
deductive question.
Disagree
7
The template provides me with a quick
reference of the various chemical tests
and reactions.
Disagree
8
The template helps me to piece
information together.
Disagree
9
The template helps me to arrive at a
final structure.
Disagree
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10
What do you like about this template?
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
11
What do you not like about this template?
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
12
What are the problems encountered when using the template?
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
13
Some suggestions for improvement:
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
____________________________________________________________________________________
Thank you for your time!
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Appendix 11
1. The template is useful.
4%
9%
9%
Strongly Disagree
2%
Disagree
Somew hat Disagree
42%
Somew hat Agree
Agree
Strongly Agree
34%
2. I know how to use the template.
9%
2%2%2%
Strongly Disagree
Disagree
36%
Somew hat Disagree
Somew hat Agree
Agree
49%
Strongly Agree
3. The template increases my confidence in solving deductive questions.
4%
6%
4%
9%
Strongly Disagree
Disagree
36%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
41%
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4. The template helps me solve deductive questions at a faster speed.
7%
4%
13%
Strongly Disagree
0%
Disagree
28%
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
48%
5. The template helps me to solve deductive questions.
6%
2%
13%
Strongly Disagree
11%
Disagree
Somew hat Disagree
38%
Somew hat Agree
Agree
Strongly Agree
30%
6. I know where to start when I see a deductive question.
11%
0%
2%
6%
17%
Strongly Disagree
Disagree
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
64%
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7. The template provides me with a quick reference of the various chemical tests and
reactions.
2%2%
6%
6%
Strongly Disagree
Disagree
Somew hat Disagree
28%
Somew hat Agree
Agree
Strongly Agree
56%
8. The template helps me to piece information together.
2%
2%
6%
23%
15%
Strongly Disagree
Disagree
Somew hat Disagree
Somew hat Agree
Agree
Strongly Agree
52%
9. The template helps me to arrive at a final structure.
0%
2%
13%
Strongly Disagree
15%
Disagree
Somew hat Disagree
44%
Somew hat Agree
Agree
Strongly Agree
26%
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