Units

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Sample subject outline - Semester 1 2013

Note: Subject outlines often change before the semester begins. Below is a sample outline.

Rationale

The synthesis of molecules from smaller parts is the ultimate expression of our knowledge of organic reactions and their mechanisms. In order to understand the diverse range of reagents and reactions used sequentially in synthesis, fundamental knowledge of key reaction mechanisms and reactivity patterns of organic molecules is essential. These topics are both intellectually challenging and of fundamental importance in the real world. Whether the context is the formation of totally new molecules, or the routine preparation of any of a vast array of useful products such as medicines, cosmetics, agrochemicals, plastics, dyes, foodstuffs etc., organic synthesis is vital to our modern lifestyle. This unit builds on the fundamentals of structure and bonding, reaction mechanisms and structure determination covered in previous units, so this unit is programmed in the fifth semester.

Aims

To expand previous organic chemistry skills and knowledge by applying higher-level thinking processes and more advanced experimental techniques to the study of organic reaction mechanisms and theoretical and practical synthetic problems.

Objectives

On successful completion of this unit you should be able to:

1. recognize electronic effects and apply mechanistic concepts that govern organic reactions and predict reaction mechanisms using the electron flow concept.
2. demonstrate a mature and critical approach to the evaluation of experimental data, especially IR and NMR spectroscopic data, and an ability to deduce and explain conclusions based on logical argument.
3. demonstrate a knowledge of a range of synthetically useful organic reactions and apply the principles of synthesis design, using the concepts of retrosynthesis.
4. apply the principles of selectivity in organic synthesis, and show knowledge of some strategies to overcome common synthetic problems.
5. demonstrate a range of practical skills in safe laboratory practice applied to the synthesis, isolation and purification of organic compounds and apply skills in information retrieval and the synthesis of experimental data and literature knowledge into coherent written reports.

Content

Organic Reaction Mechanisms

1. Structural and electronic effects in compounds of carbon; their influence on the fundamental physical and chemical properties of organic molecules.
2. Brief revision of: energetics, equilibria and kinetics; polarity and reactivity; acids and bases; nucleophilic substitution at saturated carbon.
3. Elimination reactions.
4. Nucleophilic addition to carbonyl compounds and nucleophilic acyl substitution.
5. Addition reactions of alkenes; mechanism and industrial significance to polymers and plastics.
6. Electrophilic substitution on aromatic compounds; directing influences and synthetic applications.

Organic Synthesis

1. The principles of synthesis planning; the place and goals of synthesis in modern organic chemistry; the philosophy and terminology of synthesis; the principles of functional group equivalence.
2. Carbon-carbon bond formation for the synthesis of target molecules; methods for the formation of carbon-carbon bonds in molecules containing the common functional groups; the importance of selectivity in synthesis; the role of protecting and activating groups.

Approaches to Teaching and Learning

Class contact in this unit will involve a combination of traditional lectures and less formal interactive lecture/tutorials, and a sequential laboratory experiment. Lecture notes are provided for the synthesis section, so much of the material will be presented as worked examples.

Lectures/tutorials (26 hours, 2 hours per week)
One hour of lecture time is devoted to advice on the preparation of reports on practical work.

Practical work (24 hours, 6 x 4 hour sessions)
This consists of one large experiment - a multi-step synthesis involving a protecting group. Staff of the QUT Library will present a workshop on information retrieval in organic chemistry during the first practical session.

Workshops (8 hours, 4 x 2 hours)
These interactive sessions will allow a deeper exploration or revision of selected topics from the lecture program or the techniques used in the practical exercise.

Assessment

In this unit, you will be assessed by a combination of written reports on the laboratory exercise, an individualised problem-solving task, and a written examination.The two practical reports will be returned to you with written feedback. The interim report feedback will inform your production of the final report. The 'take-home' exam will not be returned, but you are welcome to discuss your marked submission with the lecturer.

Assessment name: Laboratory/Practical
Description: Two written practical reports (an interim report after half of the experiment has been attempted, and a final report).
Relates to objectives: 2 and 5.
Weight: 30%
Internal or external: Internal
Group or individual: Individual
Due date: Weeks 8 & 11

Assessment name: Problem Solving Task
Description: A 'take-home examination' comprising individualised problems involving the proposal of synthetic routes to target molecules from nominated starting materials and the proposal of a synthetic scheme starting from an individually assigned nominated starting substance.
Relates to objectives: 3 and 4.
Weight: 35%
Internal or external: Internal
Group or individual: Individual
Due date: Week 13

Assessment name: Examination
Description: A one-and-a-half hour written examination in which you will be expected to solve unseen problems on reaction mechanisms
Relates to objectives: 1, 3 and 4.
Weight: 35%
Internal or external: Internal
Group or individual: Individual
Due date: Exam Period

Academic Honesty

QUT is committed to maintaining high academic standards to protect the value of its qualifications. To assist you in assuring the academic integrity of your assessment you are encouraged to make use of the support materials and services available to help you consider and check your assessment items. Important information about the university's approach to academic integrity of assessment is on your unit Blackboard site.

A breach of academic integrity is regarded as Student Misconduct and can lead to the imposition of penalties.

Resource materials

Recommended textbooks:

1. Bruice PY (2007) Organic Chemistry, 5th edition, Pearson Education

2. Zubrick TW (2009) The Organic Chem Lab Survival Manual, 8th Edition, John Wiley & Sons

Molecular Models:

Molecular Models may be purchased in a package with the textbook by Bruice.

Resource books containing useful information and tutorial exercises will be provided, together with details of recommended websites.

Risk assessment statement

The professional practice of Chemistry requires the safe handling of Hazardous Substances. A practical laboratory program is an important part of this unit, so you will be required to handle such substances. The chemicals and procedures used in this unit are deemed to be appropriate for students at this level of the course. You will be provided with a School Health and Safety Manual in this unit (or a pre-requisite unit). Health and Safety information and precautions relevant to the particular experiment are clearly explained in the Practical Manual. Having been provided with this information, it is your responsibility to read and comply with these instructions for the safety of yourself, your fellow students and staff.

Disclaimer - Offer of some units is subject to viability, and information in these Unit Outlines is subject to change prior to commencement of semester.

Last modified: 19-Oct-2012