CHEM2021 ORGANIC CHEMISTRY - Mechanisms and Biomolecules - UNSW Chemistry

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FACULTY OF SCIENCE

       SCHOOL OF CHEMISTRY

      CHEM2021
  ORGANIC CHEMISTRY

Mechanisms and Biomolecules

          SESSION 2, 2018
Table of Contents

1. Information about the Course ......................................................................... 2
2. Staff Involved in the Course ............................................................................. 2
3. Course Details .................................................................................................. 3
4. Rationale and Strategies Underpinning the Course ..................................... 4
5. Assessment Tasks and Feedback .................................................................. 5
6.     Course Schedule ............................................................................................. 7
7.     Additional Resources and Support................................................................ 8
8. Required Equipment, Training and Enabling Skills ...................................... 8
9. Course Evaluation and Development ............................................................. 8
11. UNSW Academic Honesty and Plagiarism ................................................. 10

                                                                                                                         1
CHEM2021 – Organic Chemistry: Mechanisms and Biomolecules
1. Information about the Course

 Year of Delivery                     2018
 Course Code                          CHEM2021
 Course Name                          Organic Chemistry: Mechanisms and Biomolecules
 Academic Unit                        School of Chemistry
 Level of Course                      2nd UG
 Units of Credit                      6UOC
 Session(s) Offered                   S2
                                      This is the main Level 2 Organic Chemistry course taught within the School of Chemistry. It assumes knowledge
 Assumed Knowledge,                   of CHEM1011 and CHEM1021 or CHEM1031 and CHEM1041 or CHEM1051 and CHEM1061, AND
 Prerequisites or Co-requisites       CHEM2041. It is a core element in Chemistry major programs. It is also required for industrial chemistry,
                                      biochemistry and medicinal chemistry programs.
 Hours per Week                       6.5 hpw
 Number of Weeks                      13 weeks (no practical session in Week 1, one lecture in Week 13 due to Labour Day public holiday in Week 10)
 Commencement Date                    23 July 2018 (UNSW S2 2018 Academic Calendar)
 Summary of Course Structure (for details see 'Course Schedule')
 Component                                     HPW                        Time                     Day                            Location
 Lectures                                        3
 Lecture 1                                                     1 pm – 2 pm                 Mon                     OMB149
 Lecture 2                                                     5 pm – 6 pm                 Tue                     ChemSciM18
 Lecture 3                                                     1 pm – 2 pm                 Fri                     ChemSciM18
 Laboratory                                     3.5
 Lab – Option 1                                                9 am – 12.30 pm             Wed                     Chem Sci 262
 Lab – Option 2                                                2.30 pm – 6 pm              Wed                     Chem Sci 262
 Lab – Option 3                                                9 am – 12.30 pm             Thu                     Chem Sci 262
 Lab – Option 4                                                2.30 pm – 6 pm              Thu                     Chem Sci 262
 TOTAL                                          6.5
                                        •    Lecturers will work through typical revision questions and problems in class.
                                        •    The first 15 minutes of each laboratory class are set aside for checking risk assessments and to
                                             cover other occupational health and safety issues.
 Special Details                        •    Lectures extend to week 13 to compensate for a public holiday in week 10.
                                        •    Bench allocation and safety induction will be carried out in week 1 in your allocated lab time (9.00-
                                             9.30 for AM lab and 2.30-3.00 for PM lab).

2. Staff Involved in the Course

                   Staff                       Role                          Name                   Contact Details               Consultation Times
                                                                                            office: Dalton Building Room 217
 Course Convenor                                                Dr Vinh Nguyen              phone: (02) 9385 6167                    By arrangement
                                                                                            e-mail: t.v.nguyen@unsw.edu.au
                                                                                            office: Dalton Building Room 226
                                                                Prof Martina Stenzel        phone: (02) 9385 4656                    By arrangement
                                                                                            e-mail: M.Stenzel @unsw.edu.au
                                                                                            office: Dalton Building Room 224
                                                                Prof Naresh Kumar           phone: (02) 9385 4698                    By arrangement
                                                                                            e-mail: n.kumar@unsw.edu.au
 Additional Teaching Staff          Lecturers & Facilitators
                                                                                            office: Dalton Building Room 217
                                                                Dr Vinh Nguyen              phone: (02) 9385 6167                    By arrangement
                                                                                            e-mail: t.v.nguyen@unsw.edu.au
                                                                                            office: Dalton Building Room 223
                                                                A/Prof Jason Harper         phone: (02) 9385 4692                    By arrangement
                                                                                            e-mail: j.harper@unsw.edu.au
                                                                Dr Vinh Nguyen              There will also be Ph.D candidate
                                                                Dr Gavin Edward             demonstrators assisting Academic
                                                                Dr Robert Chapman           Demonstrator in each laboratory
                                    Academic Demonstrators      Dr Gavin Edwards            session.
                                                                A/Prof Jason Harper
                                                                A/Prof Shelli McAlpine
                                                                Dr Adam Martin
                                    Technical & Lab Staff       Dr Nancy Scoleri            T: 9385 4722

                                                                                                                                             2
3.   Course Details

 Course Description1              Organic molecules are at the heart of the chemistry of life and industry. This course builds on the fundamental chemical
                                  principles learned in first year, exploring many of the central reactions that form the basis of living processes, modern
 (Handbook Entry)
                                  research, and contemporary industrial transformations. The course contains several modules to develop knowledge of
                                  major classes of organic reactions (including compounds containing alkenes, alkynes, aromatic rings, and carbonyl groups)
                                  by enriching a study of key reactions with an understanding of relevant reaction mechanisms. The concepts of reactivity
                                  and selectivity in the manipulation of more complex compounds will be highlighted, with an emphasis on biologically
                                  relevant molecules, especially amino acids and nucleic acids. Interleaved throughout the course will be relevant examples
                                  from contemporary chemical industries, and important medicinal and pharmaceutical examples.

 Course Aims2                     The course aims to present the chemistry of organic molecules and highlight their importance in the world around you. To
                                  achieve this, we will present four modules that will give you a framework to build further knowledge in organic chemistry
                                  with a particular emphasis on biologically relevant molecules.
                                  The aim of the experimental part of the course is to give students practical experience in a selection of the reactions that
                                  they learn about in theory, and in the experimental techniques involved in carrying out the reactions and isolating and
                                  purifying products. In addition it is designed to allow students to practise some of the skills they have learned in level 1 and
                                  to learn new skills, including structural characterisation, implementation of multi-step syntheses, proper record keeping,
                                  awareness of Laboratory Safety (http://www.riskman.unsw.edu.au/ohs/ohs.shtml).
                                  It is emphasised that the theory part of CHEM2021 builds on material covered in Chemistry I and that it is the
                                  students' responsibility to make sure they are thoroughly familiar with that material because that knowledge will
                                  be assumed.

 Student Learning                 Students will derive a good, basic understanding of most functional group chemistry, and of a reasonable number of
 Outcomes3                        carbon-carbon bond forming processes. They will have a reasonable understanding of current mechanistic theory
                                  associated with this chemistry. They will have an understanding of multistep organic synthesis design and be able to
                                  predict certain multistep reaction products. They will have the beginnings of an ability to plan organic syntheses and be
                                  able to recognise classes of compounds based on their chemical reactions and spectroscopic properties.
                                  Students will feel comfortable in entering an organic chemistry laboratory and be aware of basic safety precautions and the
                                  elements of risk assessment. They will have experience in the separation, isolation and purification of organic reaction
                                  products. They will have experience in multistep syntheses and the use of protecting groups, and they will have practised
                                  the art of structure elucidation. They will also have an understanding of the manner in which records must be kept to
                                  protect intellectual property and appreciate the need to reference information against that in the literature.
 Graduate Attributes Developed in this Course4
 Science Graduate                  Select the level                                           Activities / Assessment
                                     of FOCUS
 Attributes5
                                    0 = NO FOCUS
                                     1 = MINIMAL
                                      2 = MINOR
                                      3 = MAJOR

 Research, inquiry and                    3           The large factual content of lectures will require students to become systematic in their thinking and
 analytical thinking abilities                        inquiry, and demand that students become analytical in their management and understanding of the
                                                      concepts of organic chemistry. Students will be challenged to respond to questions during lecture times.
 Capability and motivation                3           Lectures will focus on individual performance, relying upon individual capabilities and self-motivation for
 for intellectual                                     intellectual development. Performance assessed in mid term quiz and final exam (total 65%)
 development
 Ethical, social and                      3           Lecture material will be put into an industrial context and practical classes will emphasise the need for
 professional understanding                           accurate record keeping in the generation of IP
 Communication                            2           Part of the assessment of practical reports will be based on a report, written according to journal
                                                      conventions
 Teamwork, collaborative                  2           Practical work will be performed individually and marks awarded for individual performance.
 and management skills                                Experiments need to be completed in a certain time frame, so time management will be important.
 Information literacy                     2           Practical work will require physicochemical information to be evaluated against literature data.

                         Topic 1: Stereochemistry and Mechanism                 (Prof Martina Stenzel - 9 h)
 Major Topics
                         Introduction to mechanism - the basics of mechanism; what an arrow means and how it can be used; intermediates and what they
 (Syllabus Outline)      mean; the concepts of a nucleophile and an electrophile.
                         Stereochemistry and conformation - stereogenic centres, the importance of freedom of rotation, drawing stereogenic carbon centres,

     1
       UNSW Virtual Handbook: http://www.handbook.unsw.edu.au/2013/index.html
     2
       Learning and Teaching Unit: http://www.ltu.unsw.edu.au
     3
       Learning and Teaching Unit – Learning Outcomes: http://www.ltu.unsw.edu.au/content/course_prog_support/outcomes.cfm?ss=0
     4
       Access the contextualised Science Graduate Attributes and your mapped courses: http://www2.science.unsw.edu.au/guide/slatig/sciga.html (Mapped
     courses are available at this site)

                                                                                                                                                     3
up to and including six-membered rings and a brief introduction of nomenclature (anti, syn, periplanar, etc.)
                          Addition and Elimination - introduction of E1 and E2 nomenclature, highlighting mechanistic differences, requirements in terms of
                          conformation (see above), substrate type and solvent conditions.
                          Substitution processes - introduction of SN1 and SN2 nomenclature, highlighting mechanistic differences, requirements in terms of
                          conformation (see above), substrate type and solvent conditions.
                          A comparison between substitution and elimination - use this to predict the outcome of reactions given substrate and conditions.
                          Extension to other systems - various examples such as epoxidations/ring opening.

                          Topic 2: Chemistry of carbonyl compounds (Prof Naresh Kumar - 9h)
                          This section will cover synthesis and reactivity of aldehydes and ketones, and carboxylic acid derivatives. The following topics will be
                          covered in details: nature of the carbonyl group; nucleophilic addition of water, alcohols, cyanide, amines, organometallic reagents,
                          and acetylides to carbonyl compounds, and their reaction mechanisms; reduction of the carbonyl compounds including
                          stereochemistry of carbonyl reduction; α,β−unsaturated carbonyl compounds and conjugate addition of amines, cyanide,
                          organometallic compounds; keto-enol tautomerism, reactivity of enolates, α-substitution of carbonyl compounds, α-halogenation, the
                          haloform reaction, alkylation of enolate ions and enamines; reactions of carboxylic acids and their derivatives, α-bromination of
                          carboxylic acids, reduction of carboxylic acid derivatives; carbonyl condensation reactions including the aldol reaction, the Perkin
                          reaction, the Claisen condensation reaction, and Robinson annulation reaction; application of carbonyl condensation reactions in
                          natural products synthesis. Examples (sugars, amino acids and proteins) from nature will also be provided.
                          Topic 3: Aromatic chemistry                 (A/Prof Jason Harper - 9 h)
                          Concepts of aromaticity and anti-aromaticity; non-benzenoid and anti-aromatic hydrocarbons
                          Electrophilic aromatic substitution: alkylation, acylation, halogenation, sulfonation, nitration; activating/deactivation, resonance and
                          inductive effects, directing effects, concept of blocking and protecting groups and general synthetic strategy. Reactions of
                          substituents and sidechains: alkyl- and acylbenzenes: comparison of Friedel-Crafts alkylation and acylation reactions; phenols,
                          Kolbe reaction, oxidation; selective reduction of polynitro compounds. Benzene diazonium salts: preparation, reactions, displacement
                          and coupling. Halobenzenes and nucleophilic aromatic substitution. Benzyne: preparation and reactivity. Polycyclic aromatic
                          compounds: bonding, oxidation, reduction and substitution of naphthalene and anthracene. Heterocyclic compounds: π-electron rich
                          (thiophene, furan, pyrrole) versus π -electron poor (pyridine)
                          Examples of biologically important aromatic molecules.

                          Topic 4: Chemistry of biologically relevant organic molecules (Dr Vinh Nguyen - 9h)
                          This section will cover structures, synthesis, chemical reactivity and some biological functions of naturally occuring molecules.
                          Biological systems grow, reproduce and compete with each other via a huge range of complex organic reactions. This unit will build
                          upon the knowledge of amino acids, polypeptide and proteins in Chemistry I (CHEM1021 or 1041 or 1061) to examine advanced
                          topics in chemistry of relevant biological systems to understand the important role of natural products in organic chemistry and
                          biology. Natural products are the source of the most complex and fascinating chemical structures and they represent biological
                          diversity and biological activity, whether as single compounds or as complex mixtures. Chemistry of these biologically relevant
                          molecules can be an effective bridge from tradition to modern scientific developments, including genetics, molecular biology,
                          biotechnology, and pharmaceutical science.
                          Specific topics include: primary and secondary metabolisms; amino acids, peptides and proteins; carbohydrates and
                          polysaccharides; alkaloids and steroids; terpenoids and polyketides.

 Relationship to          CHEM2021 Organic Chemistry is the main Level 2 Organic Chemistry course taught within the School of Chemistry. It assumes
 Other Courses            knowledge of CHEM1011 and CHEM1021 or CHEM1031 and CHEM1041, or CHEM1051 and CHEM1061 AND CHEM2041. It is a
 within the               core element in Chemistry major programs, required for progression into CHEM3021. It is also required for industrial chemistry,
 Program                  biochemistry and medicinal science programs. It is a recommended elective for majors such as biotechnology, geochemistry and
                          pharmacology, and it will be in the Nanoscience programme from 2015.

4.   Rationale and Strategies Underpinning the Course

 Teaching Strategies            The course will engage students in learning, at a basic level, the language of organic chemistry through a vocabulary of
                                functional group reactivity, reagents and reaction types, and the grammar of mechanistic theory and basic synthetic design. It
                                will provide a moderate range of individual practical experience in the execution of representative, single organic chemical
                                reactions and multistep synthetic sequences, while at the same time expose students to laboratory techniques, including
                                record keeping, and methods of physicochemical characterisation and spectroscopic analysis. Students in the practical classes
                                work at their own pace but are restricted in their hours of work so that they develop skills in time management.
 Rationale for learning         At this stage in their development, students have a basic understanding of organic chemistry as a field in which the
 and teaching in this           transformations of carbon-based materials from reactant to product are achieved through reactions that are promoted by use of
 course5,                       reagents. They have limited knowledge of the diverse arsenal of reactions and reagents that are available, and even less
                                practical experience of these processes. Similarly, they have little or no experience in the techniques used to characterize

     5
         LTU – Teaching Philosophy: http://www.ltu.unsw.edu.au/content/teaching_support/teaching_portfolio.cfm?ss=0#putting

                                                                                                                                                     4
molecules or their reactions. The purpose of this course is to widen the experience of the students (Engaging 1 and 2, and
                            Contextualizing 5 and 6), to introduce concepts of selectivity and rearrangement, and to engage the students in learning
                            through practical experience (Engaging 3 and Contextualizing 7), both on paper and in the laboratory.
                            This course consists of 36 hours of lectures (3 hours/week) and 36 hours of laboratory work (one 3h laboratory period/week.
                            Lectures are delivered using a combination of Powerpoint and blackboard/whiteboard presentations and they include
                            numerous worked examples (Inclusive learning 9 and Contextualizing 7). In addition, for each topic students will attempt a
                            series of short answer written exercises for which answers are provided (Engaging 2 and 3; Inclusive 9). The practical part of
                            the course reinforces chemistry that is presented in lectures (Inclusive 9). It comprises a series of single step and one multistep
                            reactions from which students are expected to isolate pure materials by a variety of techniques including distillation and
                            crystallization and to characterise them by physicochemical methods. Accurate records must be kept within individual
                            laboratory notebooks (Designing 11 and 12). In addition, the practical course involves the study of unknown substances for
                            which spectra are provided and students are expected to derive structures.
                            There is therefore an element of instruction, but also of student based learning.

5.     Assessment Tasks and Feedback

          Task           Knowledge & abilities assessed                 Assessment Criteria                % of total                 Feedback
                                                                                                             mark
                                                                                                                                WHO                HOW

     Midterm Exam on     Mechanism and Stereochemistry -           Correct answers to questions.                17          Prof Stenzel         Grade &
       Topic 1 only      Ability to predict products, suggest                                                                                   discussion
                                                                   Content shows knowledge and
                           appropriate reagents, explain
     (Monday 03rd Sep                                               understanding of the course
                               appropriate mechanisms
                                                                    material of the first section.
        – Week 8)

       Assignment 1        Carbonyl chemistry - Ability to         Correct answers to questions.                3           Prof Kumar          Annotated
                             predict products, suggest                                                                                        scripts, Marks
                           appropriate reagents, explain                                                                                       & Summary
                             appropriate mechanisms                                                                                                Chart

       Assignment 2       Aromatic compounds – Ability to          Correct answers to questions.                3          AProf Harper               ditto
                             predict products, suggest
                           appropriate reagents, explain
                             appropriate mechanisms

       Assignment 3      Naturally occurring compounds –           Correct answers to questions.                3            Dr Nguyen                ditto
                         Ability to predict products, suggest
                           appropriate reagents, explain
                               appropriate mechanisms

     Practical Reports   Practical skills and reporting ability             Also see below                      30        Practical class        Annotated
                                                                                                                          demonstrators            report

        Final Exam        Assessment of Topics 2-4 only.           Correct answers to questions.                44
                         Ability to predict products, suggest          Demonstrated deductive
                           appropriate reagents, explain                    reasoning.
                           appropriate mechanisms, and
                                   deduce structures.

       Detailed Assessment for Practical Tasks

            Task                    Assessment Criteria                       % of total                                Feedback
                                                                                mark
                                                                                                       WHO                             HOW
       Pre-lab quizzes        Pass online Moodle quizzes and                       3              Practical class             Grade & discussion.
         on Moodle           satisfactorily pass in-lab flow sheet                                demonstrators
                                          assessment

       Laboratory work     Satisfactory completion of ALL core lab                 6              Practical class             Grade & discussion.
         – core skills      skills. This is compulsory to pass the                                demonstrators
                                     practical component.

                                                                                                                                                  5
Laboratory        Maintaining an appropriate lab notebook           6            Practical class          Within 2 weeks of
   notebook                       each week                                        demonstrators           submission. Grade &
                                                                                                               discussion.

  Laboratory        Remaining laboratory assessment items,            15           Practical class          Within 2 weeks of
                               including reports                                   demonstrators           submission. Grade &
                                                                                                               discussion.

Important note: To be awarded a pass in this subject, students must satisfy these conditions:
(i)     An overall pass (≥ 50%) in the laboratory component, which requires passing all core-skills, and
(ii)    Satisfactory overall performance (≥ 40%) in the examinations (midterm and final exams for all four modules combined)
(iii)   A minimum attendance of 80% in laboratories is required.

Failure to satisfy both criteria could result in either a FL or UF (Unsatisfactory Fail) grade being awarded, or further assessment
being offered at the sole discretion of the course coordinator. Students must ensure their availability to attend any supplementary
examination that will usually be offered in the week suggested by UNSW; inability or failure to attend a supplementary examination
may lead to a FL or UF (Unsatisfactory Fail) grade being confirmed.

                                                                                                                            6
6.         Course Schedule
Some of this information is available on the Virtual Handbook6 and the UNSW Timetable7.

      Week        Lectures (Topics & Lecturers)                                  Practical                 Assignment and
                                                                                                           Submission dates (see
                                                                                                           also 'Assessment Tasks
                                                                                                           & Feedback')
      Week 1      Stereochemistry and Mechanism – Prof M Stenzel                 Lab induction and bench
                                                                                 allocation
      Week 2      Stereochemistry and Mechanism – Prof M Stenzel                 Experiment 1
      Week 3      Stereochemistry and Mechanism – Prof M Stenzel                 Finish Experiment 1

      Week 4      Carbonyl Chemistry - Prof N Kumar                              Experiment 2              Experiment 1 report is due
      Week 5      Carbonyl Chemistry - Prof N Kumar                              Experiment 3              Experiment 2 report is due
      Week 6      Carbonyl Chemistry - Prof N Kumar                              Finish Experiment 3
      Week 7      In-Class Test for Topic 1                                      Experiment 4              Experiment 3 report is due
                  (Prof Stenzel, Monday 03rd September, 1-2 pm)
                  Aromatic Chemistry – A/Prof J Harper
                  (Tuesday and Friday lectures)
     Week 8       Aromatic Chemistry – A/Prof J Harper                           Finish Experiment 4       Assignment 1 due
     Week 9       Aromatic Chemistry – A/Prof J Harper                           Experiment 5              Experiment 4 report is due
     Week 10      Aromatic Chemistry – A/Prof J Harper (Tuesday)                 Finish Experiment 5
                  Natural Product Chemistry – Dr TV Nguyen
                  (Friday)
     Week 11      Natural Product Chemistry – Dr TV Nguyen                       Experiments 6             Experiment 5 report is due
                                                                                                           Assignment 2 due
     Week 12      Natural Product Chemistry – Dr TV Nguyen                       Finish Experiment 6
     Week 13      Natural Product Chemistry – Dr TV Nguyen                                                 Experiment 6 report is due
                  (Monday – 1 lecture)                                                                     Assignment 3 due

6
    UNSW Virtual Handbook: http://www.handbook.unsw.edu.au/2013/index.html
7
    UNSW Timetable: http://www.timetable.unsw.edu.au/
                                                                                                                                 7
7.           Additional Resources and Support

    Text Books                             P. Bruice, Organic Chemistry, 7th (International Student) Edition, Pearson
                                           J. Clayden, N. Greeves, and S. Warren, Organic Chemistry, 2nd ed., Oxford University Press
                                           L. Field, S. Sternhell, J. R. Kalman, Organic Structures from Spectra, 5th ed., Wiley.

    Course Manual                          Practical Course Manual will be available only on the Moodle website

    Required Readings                      Nil

    Recommended Internet Sites             Moodle website
                                           As notified by individual lecturers

                                           Laboratory: Material Safety Data Sheets (MSDSs) for risk assessment may be obtained from the following site:
                                           http://www.chemalert.unsw.edu.au/chemalert/index/index.do

                                           Additionally, the UNSW School of Chemistry website http://www.chem.unsw.edu.au/local contains direct links to
                                           many important chemistry-related websites and databases.

    Societies                              UNSW Students of Chemistry Society (SOCS) http://www.chem.unsw.edu.au/schoolinfo/socs.html
                                           UNSW Chemical Society
                                           Royal Australian Chemical Institute http://www.raci.org.au/

    Computer Laboratories or Study         Laboratory – Chemical Sciences Building 262
    Spaces
                                           Gibson Computer laboratory – Ground floor, Dalton Building

8.           Required Equipment, Training and Enabling Skills

    Equipment Required                     Exercise book (48 or 64 page bound) for use as laboratory notebook – essential
                                           Laboratory coat, eye protection, sensible clothing, and enclosed footwear, are required in all School of Chemistry
                                           laboratories.
                                           Open-weave shoes, e.g., trainers or gym shoes, should NOT be worn in the laboratory.

    Enabling Skills Training               Compulsory OH&S briefing and lab introduction in Week 1 in Lab. 262 (please arrive ON TIME).
    Required to Complete this
    Course                                 You must attend your own lab group because laboratory work will commence in week 2.
                                           Each experiment has a safety exercise that must be completed and checked before the experimental work can
                                           commence.
                                           MSDSs can be sourced from the websites listed above, and other safety data are supplied, and training is provided as
                                           part of the class.
                                           Awareness of School plagiarism guidelines (contained on-line and in the Laboratory Manual).

9.           Course Evaluation and Development

Student feedback is gathered periodically by various means. Such feedback is considered carefully with a view to acting on it constructively
wherever possible. This course outline conveys how feedback has helped to shape and develop this course.

    Mechanisms of Review        Last Review Date        Comments or Changes Resulting from Reviews

    Major Course Review         Nov 2011                Students appreciated the blocks of lectures and liked the assignments for each block of lectures.
                                                        More worked exercises have been included in the lectures in response to student demand.
                                                        Students were largely happy with the practical course, although they noted that it required them to be
                                                        organized.

    CATEI8                                              As above.

8
    Science CATEI procedure: http://www2.science.unsw.edu.au/guide/slatig/catei.html
                                                                                                                                                            8
Other                                        Informal feedback from service Faculties and Schools indicate that CHEM2021 is a valued course that
                                                 provides the most comprehensive and useful coverage of organic chemistry for their needs.
                                                 Students have referred to the practical component as 'fun' because of the challenging range of
                                                 experiments and techniques that the course provides. They also note that the content is about right in
                                                 terms of time demand.

10.         Administration Matters

    Expectations of Students     Assessment. Assessment for CHEM2021 is based upon:
                                       •    midterm exam (17% on topic 1),
                                       •    marks for three assignments (9%, 3% each for topics 2, 3 and 4),
                                       •    practical marks (30%), and
                                       •    one 2 hour written examination (44% on Topics 2-4).

                                   Important note: To be awarded a pass in this subject, students must satisfy these conditions:
                                   (i)    An overall pass (≥ 50%) in the laboratory component, which requires passing all core-skills, and
                                   (ii)   Satisfactory overall performance (≥ 40%) in the examinations (all four modules combined)
                                   (iii)  A minimum attendance of 80% in laboratories is required.

                                   Failure to satisfy both criteria could result in either a FL or UF (Unsatisfactory Fail) grade being awarded, or further
                                   assessment being offered at the sole discretion of the course coordinator. Students must ensure their availability to
                                   attend any supplementary examination that will usually be offered in the week suggested by UNSW; inability or
                                   failure to attend a supplementary examination may lead to a FL or UF (Unsatisfactory Fail) grade being confirmed.

                                 Attendance. Unless a specific exemption is granted by the School, a minimum attendance rate of 80% in each component
                                 of the course (lecture and laboratory) is required before a candidate can be considered for a pass in the course (see
                                 UNSW Policy https://my.unsw.edu.au/student/atoz/AttendanceAbsence.html).
                                 Attendance at Laboratory Classes is compulsory and a roll is kept. The reasons for any absences should be conveyed to
                                 the Laboratory Supervisor. If these were due to health problems they should be documented with a medical certificate. In
                                 such genuine instances no additional laboratory time will be allowed, but the laboratory marks obtained during session
                                 may be scaled accordingly so that you are not disadvantaged.
                                 Laboratory Work: pre-laboratory work is expected to take 15-30 minutes per week (including safety matters) and post-
                                 laboratory write-up is expected to take no more than 30 minutes per week.
                                 Ethical Practice. Students are expected to conduct themselves in a sensible and ethical manner, especially with regard to
                                 plagiarism, and in computer use, including the use of email and online discussion forums.

    Assignment Submissions       Lecture Assignments must be submitted to the lecturer concerned and a School Assignment/Report Cover Sheet must be
                                 attached (available on the Moodle website and in the School Office).
                                 Laboratory Reports will be submitted during the normal laboratory period.
                                 Late submission: Late submission of an assessment task without an approved extension of the deadline is not
                                 acceptable. Marks will be deducted for late submission at the rate of 10% of the total possible marks for that particular
                                 assessment task per day. This means that if a piece of work is marked out of 100, then the late penalty will be 10 marks
                                 per day (10% of 100 possible marks per day). The formula for calculating the late penalty is the total possible marks x 0.10
                                 x number of days late. For the purposes of this policy a weekend (Saturday and Sunday) will be regarded as two days.

    Occupational Health and      Information on relevant Occupational Health                and    Safety    policies   and     expectations    at    UNSW:
    Safety9                      http://www.ohs.unsw.edu.au/ohs_hazards/index.html
                                 School of Chemistry OH&S policy and requirements see laboratory manual.
                                 To be admitted to a laboratory, you must wear safety glasses meeting the minimum size requirements as posted outside
                                 all teaching laboratories, a lab coat and covered shoes (no thongs, open sandals or clogs). You must also complete all
                                 safety pre-lab work, risk assessment or other prescribed preparation relating to carrying out safe laboratory work.
                                 Visitors are not allowed to undergraduate laboratories without the permission of the lab supervisor.

    Assessment Procedures        Exemption for practical classes can be given to repeating students providing they have completed the course to a
                                 satisfactory level within the past 3 years. Applications for exemption should be made to the Course Coordinator, Dr Vinh
                                 Nguyen, Dalton Room 217), before the start of session. Permission will not normally be given for students to swap
                                 laboratory classes nor attend make up classes. Any requests based on medical grounds should be addressed to the
                                 Course Coordinator, but permission should not be assumed.

9
    UNSW Occupational Health and Safety: http://www.hr.unsw.edu.au/ohswc/ohswc_home.html
                                                                                                                                                       9
Equity and Diversity                  Those students who have a disability that requires some adjustment in their teaching or learning environment are
                                           encouraged to discuss their study needs with the course Convenor prior to, or at the commencement of, their course, or
                                           with the Equity Officer (Disability) in the Equity and Diversity Unit (9385 4734 or http://www.studentequity.unsw.edu.au/ ).
                                           Issues to be discussed may include access to materials, signers or note-takers, the provision of services and additional
                                           exam and assessment arrangements. Early notification is essential to enable any necessary adjustments to be made.

     Grievance Policy10                    School Contact                            Faculty Contact                                      University Contact

                                           Dr Gavin Edwards                          A/Prof Janelle Wheat                                 Student Conduct and Appeals
                                           Dir. of Teaching                          Associate Dean (Education)                           Officer (SCAO) within the Office of
                                           School of Chemistry                       jwheat@unsw.edu.au                                   the Pro-Vice-Chancellor (Students)
                                                                                                                                          and Registrar.
                                           g.edwards@unsw.edu.au                     Tel: 9385 0752
                                                                                                                                          studentcomplaints@unsw.edu.au
                                           Tel: 9385 4652
                                                                                                                                          Tel: 9385 8515

                                                                                                                                          University Counselling and
                                                                                                                                          Psychological Services
                                                                                                                                          Tel: 9385 5418

11. UNSW Academic Honesty and Plagiarism

     What is Plagiarism?

     Plagiarism is the presentation of the thoughts or work of another as one’s own.
     *Examples include:
     • direct duplication of the thoughts or work of another, including by copying material, ideas or concepts from a book, article, report or other written
          document (whether published or unpublished), composition, artwork, design, drawing, circuitry, computer program or software, web site, Internet, other
          electronic resource, or another person’s assignment without appropriate acknowledgement;
     • paraphrasing another person’s work with very minor changes keeping the meaning, form and/or progression of ideas of the original;
     • piecing together sections of the work of others into a new whole;
     • presenting an assessment item as independent work when it has been produced in whole or part in collusion with other people, for example, another
          student or a tutor; and
     • claiming credit for a proportion a work contributed to a group assessment item that is greater than that actually contributed.†

     For the purposes of this policy, submitting an assessment item that has already been submitted for academic credit elsewhere may be considered plagiarism.

     Knowingly permitting your work to be copied by another student may also be considered to be plagiarism.

     Note that an assessment item produced in oral, not written, form, or involving live presentation, may similarly contain plagiarised material.

     The inclusion of the thoughts or work of another with attribution appropriate to the academic discipline does not amount to plagiarism.

     The Learning Centre website is main repository for resources for staff and students on plagiarism and academic honesty. These resources can be located
     via:

     www.lc.unsw.edu.au/plagiarism

     The Learning Centre also provides substantial educational written materials, workshops, and tutorials to aid students, for example, in:
     • correct referencing practices;
     • paraphrasing, summarising, essay writing, and time management;
     • appropriate use of, and attribution for, a range of materials including text, images, formulae and concepts.

     Individual assistance is available on request from The Learning Centre.

     Students are also reminded that careful time management is an important part of study and one of the identified causes of plagiarism is poor time
     management. Students should allow sufficient time for research, drafting, and the proper referencing of sources in preparing all assessment items.

     * Based on that proposed to the University of Newcastle by the St James Ethics Centre. Used with kind permission from the University of Newcastle
     † Adapted with kind permission from the University of Melbourne

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     UNSW Grievance Policy: http://www.policy.unsw.edu.au/policy/student_grievance_resolution.pdf
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