CVB204 Organic Structure and Mechanisms


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Unit Outline: Semester 2 2024, Gardens Point, Internal

Unit code:CVB204
Credit points:12
Pre-requisite:((CVB101 or CZB191) and (CVB102 or CZB191)) or ((CVB102 or CVB103 or CZB190) and admission to ST20)
Anti-requisite:PQB401
Coordinator:Steven Bottle | s.bottle@qut.edu.au
Disclaimer - Offer of some units is subject to viability, and information in these Unit Outlines is subject to change prior to commencement of the teaching period.

Overview

Build on the organic chemistry knowledge and laboratory skills gained in CVB101 and CVB 102. The deeper understanding of reaction mechanisms, instrumental characterisation and stereochemistry are important in facets of all subsequent chemistry units. Perhaps most importantly, this unit will be used as the foundation for advanced studies in organic chemistry in CVB 301 Organic Chemistry: Strategy for Synthesis.

To successfully complete this unit you will:
-Describe the electronic effects and mechanistic concepts which govern the reactions of organic compounds.
-Predict the outcome of a set of reaction conditions when applied to organic compounds.
-Design syntheses based on the major functional groups.
-Deduce the solution of synthetic problems in organic chemistry
-Apply modern spectroscopic techniques as an aid to structure elucidation
-Demonstrate a range of practical skills in safe laboratory practice applied to the synthesis, isolation and purification of organic compounds.

Learning Outcomes

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

  1. Recognize chirality in organic molecules and its practical consequences.
  2. Describe the electronic effects and mechanistic concepts which govern the reactions of organic compounds.
  3. Predict the outcome of an unfamiliar set of reaction conditions when applied to simple organic compounds.
  4. Design simple syntheses and interconversions based on the major functional groups.
  5. Deduce the solution of chemical and synthetic problems in organic chemistry.
  6. Apply modern spectroscopic techniques as an aid to structure elucidation.
  7. Demonstrate a range of practical skills in safe laboratory practice applied to the synthesis, isolation and purification of organic compounds and document these findings in an appropriate work oriented format

Content

This unit will build on the foundation of organic chemistry laid in CVB102. The unit will revisit a number of the reactions previously investigated, but will build towards a deeper understanding through study of mechanisms of reaction. The understanding gained from mechanisms in organic synthesis will then be extended to advanced synthetic reactions and implications of structure (stereochemistry) on synthesis.
Finally with greater understanding of synthetic reactions and structurally more complex reaction products, there will be a realisation that the spectroscopic techniques applied in CVB101 will not always suffice for structural determination. Therefore a number of advanced molecular spectroscopy techniques will be introduced that will be built upon further in CVB301.
We will adopt a guided approach to learning in each of these key areas (below) leading from experimental result to conceptual model to predictability and testability. Successful learning will depend on recall of relevant factual material as a necessary preparation for solving problems.
Material covered will include but is not limited to:
  • Introduction to modern concepts in organic synthesis
  • Stereochemistry
  • Reactions in organic chemistry
  • Introduction to organic mechanisms
  • Molecular spectroscopy: Ultraviolet, infra-red and nuclear magnetic spectroscopy

Learning Approaches

Approaches to teaching and learning
Class contact in this unit will involve a combination of traditional lectures and less formal interactive workshop/tutorials, and a sequential laboratory experiment.
Lectures/tutorials (26 hours, 2 hours per week)
Interactive lectures using appropriate real world examples to demonstrate theory and concepts combined with collaborative problem solving in groups with feedback and discussion with the larger class.
Practical work (24 hours, 6 x 4 hour sessions)
The practical program is designed to reinforce the practical skills you learnt in CVB102 as well as develop more advanced skills in the syntheses, isolation and purification of organic compounds. Your acquisition of the knowledge and skills in the practical aspects of the safe handling and use of organic chemicals and reagents is emphasised. You will be able to work individually and collaboratively as members of a team in laboratory settings to develop thes practical skills. .
Workshops (10 hours, 5 x 2 hours)
These inquiry based interactive sessions will allow a deeper exploration or revision of selected topics from the lecture program or the techniques used in the practical exercise.

Feedback on Learning and Assessment

Feedback to students
There will be extensive opportunity to assess your progress in the unit. By attendance and participation in the tutorial program, you will be able to assess your understanding of the lecture material. The informal atmosphere in the laboratory means that you will have the opportunity for one-to-one feedback from your demonstrator. The results that you obtain in the problem solving assignment will provide ongoing feedback, in particular about your preparation for the final theory exam. All staff in the unit will be available for individual or small group consultation.

Assessment

Overview

General Assessment Information
The assessment in this unit comprises both formative and summative elements. Formative assessment will take the form of provision of model answers for summative tasks, practice problems with worked solutions, regular feedback on your practical workbook, and interactive discussions with your laboratory demonstrators. Summative assessment is a combination of problem-solving tasks, final submission of the laboratory workbook, a literature supported written paper/report? and supervised written theory examination.

Unit Grading Scheme

7- point scale

Assessment Tasks

Assessment: Workbook

You will be required to undertake six 4-hour sessions of supervised practical work for which you will maintain a laboratory workbook which documents the reaction being performed (including description of the mechanism), description of the synthetic procedure and workup and an analysis of the spectroscopic data used to characterise your compounds.

This is an assignment for the purposes of an extension.

Weight: 30
Individual/Group: Individual
Due (indicative): ongoing
Related Unit learning outcomes: 6, 7

Assessment: Research Paper

You will research and write up a series of individualised problems involving the elucidation of chemical structure through evaluation of spectroscopic data based on real examples from the literature.

This is an assignment for the purposes of an extension.

Weight: 25
Individual/Group: Individual
Due (indicative): 09/11/2019
Related Unit learning outcomes: 5, 6

Assessment: Examination (written)

The end of semester theory exam will cover content from all theory components of the unit.

 

Weight: 45
Individual/Group: Individual
Due (indicative): end of semester
Related Unit learning outcomes: 1, 2, 3, 4, 5, 6, 7

Academic Integrity

Students are expected to engage in learning and assessment at QUT with honesty, transparency and fairness. Maintaining academic integrity means upholding these principles and demonstrating valuable professional capabilities based on ethical foundations.

Failure to maintain academic integrity can take many forms. It includes cheating in examinations, plagiarism, self-plagiarism, collusion, and submitting an assessment item completed by another person (e.g. contract cheating). It can also include providing your assessment to another entity, such as to a person or website.

You are encouraged to make use of QUT’s learning support services, resources and tools to assure the academic integrity of your assessment. This includes the use of text matching software that may be available to assist with self-assessing your academic integrity as part of the assessment submission process.

Further details of QUT’s approach to academic integrity are outlined in the Academic integrity policy and the Student Code of Conduct. Breaching QUT’s Academic integrity policy is regarded as student misconduct and can lead to the imposition of penalties ranging from a grade reduction to exclusion from QUT.

Resources


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.

Resource Materials

Recommended text(s)

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

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

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 undertake compulsory formal pre-laboratory assessment in Health and Safety matters relevant to the laboratory and QUT buildings in general. Health and Safety information and precautions relevant to the particular experiments are clearly explained in the Practical Manual. Having been provided with this advice, it is your responsibility to comply with all instructions, for the safety of yourself, your fellow students and staff.

Course Learning Outcomes

This unit is designed to support your development of the following course/study area learning outcomes.

ST01 Bachelor of Science

  1. Develop a broad, multidisciplinary understanding of science and a specialised, in-depth knowledge of at least one discipline.
    Relates to: Examination (written)
  2. Use higher order thinking skills to design, plan, and conduct investigations and evaluate data to address scientific questions and challenges.
    Relates to: Examination (written)
  3. Develop and demonstrate key competencies in scientific practices and relevant technologies.
    Relates to: Examination (written)
  4. Practice science in a safe, culturally appropriate, ethical, sustainable, and socially conscious way with a knowledge of relevant concepts, regulatory frameworks and protocols.
    Relates to: Examination (written)
  5. Communicate scientific findings, concepts and evidence-based reasoning to diverse audiences using a variety of methods.
    Relates to: Examination (written)