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EZ Research Monographs • VOL. 1 2009149

Using a Dialectic Soft Systems Methodology (DSSM) to construct a Template for Answering Organic Deductive

Questions in Advance Level Chemistry

Aileen LimLow Kian SehTearle Cheng

Tng Miao Hui andLi 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.

Justifi cations 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



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.

Justifi cations 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



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)



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 clarifi cation

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.

1st Dialectic Finding out and seeking clarification

Define the Essence (summary of selected practice)

Immersion from Reality (Actual teaching)

2nd Dialectic Derivation of Template

Partial Organic Template

3rd Dialectic Refinement of template

4th Dialectic Evaluation of template

Final Organic Template

Figure 1



Reasons for Liking Organic Chemistry

Reasons for Disliking Organic Chemistry

Interesting and fun, Questions are hard The challenge and thinking involved are enjoyable

Organic structures are hard to deduce

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 do not need to be lengthy

Same reaction can have multiple reagents & 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).

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.



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

Knowledge (Stage 1)

Difficulty in remembering too many mechanisms, reactions, equations, reagents and/or conditions

Knowledge (Stage 1)

Confusion in various reactions and reagents & conditions

Comprehension (Stage 2)

Difficulty in applying concepts learnt to larger/more complex molecules

Application (Stage 3)

Difficulty in distinguishing between organic compounds and/or functional groups

Analysis (Stage 4)

Difficulty in making appropriate deductions Analysis (Stage 4) Difficulty in piecing information together to arrive at final structure

Synthesis (Stage 5)

Difficulty in linking the concepts from various topics together

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.



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: Refi nement 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



Problems encountered by student with accompanying quotes.

Refinements made to template

“unclear what deductions could be made from insoluble in water and soluble in NaOH(aq)”

Insolubility in water was inserted under the general deductions in stage 1. Also examples of common bases used in organic reactions are listed down.

“cannot find NaOH as reagent” This particular reagent was left out inadvertently.

Reagent was inserted into stage 2 of the template.

“not sure how to explain reactions of G” Students were unable to explain reactions that are taking place for each of the chemical tests listed in stage 2 of the template.

The type of reaction and also the mechanism were inserted into the ‘functional group’ column and the term ‘deduction’ was added to the Heading.

It was noted that the template was also not consistent in the area of presentation. For stage 2, some tests had negative test incorporated while others did not. Though it 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.

Negative tests were inserted into the template to make it more consistent and also to train students that deductions could be made from tests which are negative.

“Don’t know how to arrive to the structure using the deductions”

Stage 3 of the template helps students to link 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.

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.

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.

Table 3: Problems that Students Encountered with the Template, and Corresponding Refi nements



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.

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.

Table 4: Reasons for Liking the Organic Chemistry Template

Reasons for liking the template

Category Number of respondents (Total 47) with such responses

Organized, concise, easy to read, good summary, easy to memorize, comprehensive

Organization, details and presentation

34 (72.3 %)

Easy to use / refer to / identify / deduce, has useful information, know where to start

Ease of usage and application to question

16 (34.0 %)

Allows for quick reference, helps solve the question quickly

Improving students’ speed at solving

4 (8.5 %)

Teaches to use step by step, breaks process into stages

Systematic scaffolding 3 (6.4 %)



Reasons for not liking the template


Missing Information, details, deductions / reactions and/or equations

Content 27 (57.4 %)

Template is not well-organized Organization and presentation

1 (2.1 %)

Difficulty in usage, or that the template was not helpful and/or applicable to question


3 (6.4 %)

Flipping through the template takes time

Improving students’ speed at solving

2 (4.3 %)

The template doesn’t help enough in linking information together


No response 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.



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.

Problems encountered when using the template


Missing Information, details ,deductions/reactions, and/or equations

Content 10 (21.3 %)

Template is hard to read and/or messy

Organization and presentation

2 (4.3 %)

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


13 (27.7 %)

Difficulty in making deductions and/or linking information together


No response / no problem 17 (36.2 %)



Suggestions for Improvement Category Number of respondents (Total 47) with such responses

Include more information, details, reactions, reagents, equations

Content 15 (31.9 %)

Group reactions for specific compounds together, be more organized, use diagrams, and/or draw structures

Organization and presentation

4 (8.5 %)

Show examples of more questions


1 (2.1 %)

Demonstrate how to piece together the final structure

Systematic scaffolding

1 (2.1 %)

Do not use template again 2 (4.3 %) No response or that the template is good enough

21 (44.7 %)

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).


The problems encountered by the students while using the final version of the template were summarized in Table 8.



Problems encountered by student with accompanying quotes.

Refinements made to template

“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.

The reagent sodium hydrgencarbonate is incorporated into the template.

“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.

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.

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.

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.

“No NaCN and HCN in template. Don’t know what to deduce.” These reagents do not fall under the category of chemical tests.

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 Refi nements


The problems encountered by the students while using the final version of the template were summarized in Table 8.



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.



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.



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 Self-evaluation 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.



1 I like Organic Chemistry.

Reasons: ____________________________________________________________________________ ____________________________________________________________________________

2 I am good in Organic Chemistry.

3 I enjoy solving deductive questions.

4 I am confident in solving deductive

questions.

5 I am quick in solving deductive

questions.

6 I have problems coping with Organic

Chemistry.

List down the problems you faced:

____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________

7 I find solving deductive questions a tedious chore.

Strongly Agree

Agree Somewhat Agree

Somewhat

Disagree

Disagree Strongly Disagree

O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

O O O O O O

Agree Disagree Somewhat

Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O

Strongly Disagree

Disagree Somewhat

Disagree

Somewhat Agree

Agree Strongly Agree

Appendix 1

Survey Questions

Please rate how strongly you agree or disagree with each of the following statements by shading the appropriate circles



Possible reasons are:

(i) When I see a deductive question, I usually do not know where to start.

Reasons why you know/ do not know where to start:

_____________________________________________________________________ _____________________________________________________________________ _____________________________________________________________________

(ii) I can easily recall the reactions of various functional groups.

(iii) I can easily recall the reagents and

conditions of chemical tests I have learnt.

(iv) I know the relevant chemical tests to

distinguish between various functional groups.

(v) I can easily write balanced equations

for various reactions.

(vi) I can recall reagents and conditions

but I am confused about what functional groups they are used to test for.

(vii) I have difficulty remembering the various chemical tests.

(viii) I am usually able to think of various

possible functional groups by analyzing the given molecular formula(e).

(ix) I am usually able to pick out relevant information from deductive questions.

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O

Strongly Disagree

Disagree Somewhat

Disagree

Somewhat Agree

Agree Strongly Agree



(x) I am usually able to make deductions based on the information gathered.

(xi) I am usually able to see links between

the multiple deductions made.

(xii) I am usually able to arrive at a final

structure.

(xiii) I usually do not know how to use the

deductions made to deduce the final answer.

(xiv) I find problems phrasing and

presenting my answers.

Others:

____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

Thank you for your time!



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

Where : R Or H3C C

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.

Appendix 2



• 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 H H OH

H3C C CH3 CH2C CH2 C C

H H • M is

C

O OH

H3C CH2 C O

• 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.



1. I like Organic Chemistry.

7%8%

19%

45%

18%3%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

2. I am good in Organic Chemistry.

19%

14%

45%

20%

2% 0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

3. I enjoy solving deductive questions.

9%

14%

21%41%

13%2%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

Appendix 3



4. I am confident in solving deductive questions.

5. I am quick in solving deductive questions.

30%

15%36%

16%

3%0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

38%

16%

31%

11%3%1%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

6. I have problems coping with Organic Chemistry.

7. I find solving deductive questions a tedious chore.

2% 7%

19%

40%

22%

10% Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

5%12%

17%

39%

19%

8%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



7(i) When I see a deductive question, I usually do not know where to start.

4%12%

27%

30%

21%

6%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(ii) I can easily recall the reactions of various functional groups.

15%

17%

42%

22%

4%

0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(iii) I can easily recall the reagents and conditions of chemical tests I have learnt.

20%

18%

38%

23%

1% 0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



(iv) I know the relevant chemical tests to distinguish between various functional groups.

9%

15%

19%52%

5%

0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(v) I can easily write balanced equations for various reactions.

9%

16%

25%

35%

14% 1%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(vi) I can recall reagents and conditions but I am confused about what functional groups they are used to test for.

5% 9%

21%

40%

17%

8%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



(vii) I have difficulty remembering the various chemical tests.

2%5%

15%

38%

25%

15%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(viii) I am usually able to think of various possible functional groups by analyzing the given molecular formula(e).

5% 7%

15%

51%

20%

2%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(ix) I am usually able to pick out relevant information from deductive questions.

3%4%12%

46%

31%

4%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



(x) I am usually able to make deductions based on the information gathered.

(xi) I am usually able to see links between the multiple deductions made.

5%11%

13%

52%

15%4%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

8%

12%

27%37%

14%2%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(xii) I am usually able to arrive at a final structure.

11%

19%

34%

28%

8% 0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



(xiv) I find problems phrasing and presenting my answers.

1% 12%

18%

29%

21%

19% Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

(xiii) I usually do not know how to use the deductions made to deduce the final answer.

4%17%

22%

35%

16%

6%Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



Reagents and Conditions

Observations Functional groups

H2 -OH group Na (s)

No H2 No - OH group

Brady’s reagent 2,4-dinitrophenylhydrazine

Orange ppt Carbonyl compound eg aldehyde, RCHO or ketone, RCR’ present O

No orange ppt Absence of carbonyl compounds

Reagents and Conditions

Observations Functional groups

Fehling’s Alkaline solution of Cu2+ tartrate, heat

Reddish-brown ppt

Organic compound easily oxidized. Presence of aldehyde except benzaldehyde

No reddish-brown ppt Absence of aliphatic aldehyde

Initial Deductive Stage 1 (General Deductions)

Properties Deductions Possible functional groups High Highly

unsaturated. Aromatic

Presence of benzene ring 1. C: H ratio

Low Aliphatic Absence of benzene ring Base Acidic in

nature Phenol, -CO2H 2. Soluble in

Water Able to form hydrogen bonds with water molecules

-OH, -CO2H group present

Solid High mp High Mr 3. Physical state Gas Very low bp Low Mr

1 oxygen atom -OH 4. Formula 2 oxygen atoms Two -OH groups, -CO2H

Stage 2 (Specific Deductions)

Appendix 4



Tollen’s Ammonical silver(I) nitrate, heat

Silver mirror Organic compound easily oxidized. Presence of aldehydes

No silver mirror Absence of aldehyde Yellow ppt

OH Presence of CH3C R H Where R : H, alkyl or benzene ring

Iodoform test Alkaline aq. Iodine/ heat

No yellow ppt

OH Absence of CH3C R H Where R : H, alkyl or benzene ring

Decolourisation Compound unsaturated, C=C present

Br2/CCl4

No decolourisation Absence of C=C

Decolourisation with white ppt -OH group attached directly to benzene ring eg. phenolic group

Br2(aq)

Decolourisation Presence of C=C

White fumes of HCl Presence of -OH except phenol

PCl5 or SOCl2

No white fumes Absence of –OH

Na2CO3 Effervescence of CO2

Sample acidic, presence of -CO2H

No effervescence Sample not acidic, absence of -CO2H

Neutral FeCl3 Violet complex Phenolic group present i.e. -OH group attached directly to benzene ring

Acidified K2Cr2O7 or KMnO4, heat

Orange dichromate turned green or Decolourisation of acidified KMnO4

Compound can be oxidized e.g. could be primary or secondary alcohol



Stage 3 (Linking Information Together)

Reaction Observations Deductions [ O] Alkene X Y + CO2 Less C atoms in Y or effervescence (CO2 evolved)

Terminal alkene, RC=CH2 R’ Where R, R’ = H or alkyl group

[ O] Alkene X Y Number of C atoms in Y is half of the number of C atoms in X

Symmetrical alkene, RC=CR R’ R’

Oxidation KMnO4, acidified, reflux

[ O] Alkene X Y + Z Both Y and Z are ketones Both Y and Z are carboxylic acids Y is ketone and Z is carboxylic acid

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 RC=CR’ H H RC=CR’ R H



[ O] Alkene X Y Same number of C atoms in X and Y

Cyclic alkene with one double bond.

Reaction Observations Deductions Dehydration Al2O3, heat or excess concentrated H2SO4, 180 °C

Removal of H2O molecule from alcohol to form alkene

H H H H R-C=C-CH2R’ RCH2C=CR’

H H H

H

C C C

OH H

R R’



2-methylpropanoic acid

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:

B 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.

B D: Since B contains -CH2OH, dehydration gives only one alkene (D) and D is a terminal alkene.

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.

Appendix 5



Compound Structure

B CH3-CH-CH2-CH2-OH | CH3

C CH3-CH-CH2-CO2H | CH3

D CH3-CH-CH=CH2 | CH3

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.

OH CH3CH2 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 II C8H8Cl2O E C8H8Cl2O F Cl2(aq) G (a) (i) Suggest a structural formula for compound F.

OH

Cl

Cl

CH3CH2

(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

Appendix 6



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 OH G: H: C

Cl

C

OH

OHCH3 OHCH3 J:

C OHCH3 O On reaction with aq. NaOH, nucleophilic substitution occurs:

+ 2 OH- + 2 Cl- C

Cl

C

OH

CH3 OH OH CH3

Cl OH

G H Since the two hydroxyl groups are on the same carbon atom, H immediately loses water to give J. + H2O C

OH C OH CH3CH3 OH O OH

JH J is a ketone with a carbonyl functional group and reacts with 2,4-dinitrophenylhydrazine to give an orange ppt of 2,4-dinitrophenylhydrazone.



C O

CH3

+NO2

NO2

H2NNH

C

CH3 NO2

NO2

NNH

+ H2O

HO HO

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.



App

endi

x 7

Wor

king

shee

t for

doc

umen

ting

Prob

lem

s E

ncou

nter

ed

Pr

oble

ms

Enc

ount

ered

Prob

lem

s E

ncou

nter

ed

Pr

oble

ms

Enc

ount

ered

St

ruct

ure

A

Stru

ctur

e D

Str

uctu

re C

Stru

ctur

e B



Appendix 8











P and Q contains benzene ring

P undergoes neutralization with sodium hydrogencarbonate.

P is a carboxylic acid P undergoes oxidation with hot acidified KMnO4 to form product with 2 carbon atoms less.

P is an alkene

Q undergoes oxidation with hot acidified KMnO4 to liberate CO2. Q is a terminal alkene

P undergoes electrophilic addition with aqueous Br2 in the dark

P is an alkene

Q undergoes electrophilic substitution with aqueous Br2 Q is a phenol

T undergoes elimination with excess concentrated H2SO4 to form Q

T is an alcohol

T undergoes oxidation with alkaline iodine

T contains

C

H

CH3

OH

Q undergoes nucleophilic addition with a mixture of NaCN and HCN to from U. Q is carbonyl compound

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.

Appendix 9

Answers



C

H

OH

CH3C

O

HO

T

Excess conc H2SO4, 170°C

C

H

CC

O H

H

HO

HCN/NaCN

QC

H

CC

H

OH

O

C

H

CC

O H

H

OH

Br2 (aq)

C

H

CC

OH H

H

HO

CN

U

OR Br2 (aq)

P

C

H

CC

O

H

H

HO

Br

Br

OH Br

S

C

H

CC

H

OH

O

OH Br

R

OROR

C

H

CC

O

H

H

HO

Br

Br

Br OH

C

H

CC

H

OH

O

Br OH



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.

2 I know how to use the template.

3 The template increases my confidence

in solving deductive questions.

4 The template helps me to solve

deductive questions at a faster speed.

5 The template helps me solve deductive

questions.

6 I know where to start when I see a

deductive question.

7 The template provides me with a quick

reference of the various chemical tests and reactions.

8 The template helps me to piece

information together.

9 The template helps me to arrive at a

final structure.

O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

Strongly Agree


Somewhat

Disagree


O O O O O O

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

O O O O O O


Disagree

Somewhat Agree

Strongly Agree

Strongly Disagree

Appendix 10



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!



1. The template is useful.

9%

9%

2%

34%

42%

4%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

2. I know how to use the template.

2%2%2%

36%

49%

9%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

3. The template increases my confidence in solving deductive questions.

6%4%

9%

41%

36%

4%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

Appendix 11



4. The template helps me solve deductive questions at a faster speed.

4%13%

0%

48%

28%

7%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

5. The template helps me to solve deductive questions.

2%13%

11%

30%

38%

6%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

6. I know where to start when I see a deductive question.

0%2% 6%

17%

64%

11%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree



7. The template provides me with a quick reference of the various chemical tests and reactions.

2%2% 6%

28%

56%

6%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

8. The template helps me to piece information together.

2% 6%

15%

52%

23%

2%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree

9. The template helps me to arrive at a final structure.

13%

15%

26%

44%

2%

0%

Strongly Disagree

Disagree

Somew hat Disagree

Somew hat Agree

Agree

Strongly Agree


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Using a Dialectic Soft Systems Methodology (DSSM) to ... @ East Zone... · EZ Research Monographs • VOL. 1 2009 149 Using a Dialectic Soft Systems Methodology (DSSM) to construct