Students

CHEM3601 – Advanced Synthesis

2022 – Session 2, In person-scheduled-weekday, North Ryde

General Information

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Unit convenor and teaching staff Unit convenor and teaching staff Unit Convenor and Lecturer
Andrew Piggott
andrew.piggott@mq.edu.au
Contact via 98508251
4WW 334
By appointment (please email)
Lecturer
Fei Liu
fei.liu@mq.edu.au
Contact via 98508312
4WW 330
By appointment (please email)
Lecturer
Koushik Venkatesan
koushik.venkatesan@mq.edu.au
Contact via 98508296
4WW 123
By appointment (please email)
Credit points Credit points
10
Prerequisites Prerequisites
20cp in CBMS or BMOL or CHEM units at 2000 level or above including (CHEM2601 or CBMS203 or CBMS204)
Corequisites Corequisites
Co-badged status Co-badged status
Unit description Unit description

This unit examines advanced topics in modern synthetic organic and inorganic chemistry. Specific topics may include: synthesis with selectivity, coordination chemistry, heterocyclic chemistry, rearrangement reactions, pericyclic reactions and advanced spectroscopic methods. These topics build upon the foundation of "CHEM2601 Synthesis", using the same text books supplemented with inexpensive Oxford Chemistry Primers on the specified topics. This unit requires strong skills in organic and inorganic chemistry, while a background in other aspects of chemistry will be advantageous. The laboratory sessions are aimed at developing skills in organic and inorganic synthesis and in the spectroscopic identification of organic and inorganic compounds.

Important Academic Dates

Information about important academic dates including deadlines for withdrawing from units are available at https://www.mq.edu.au/study/calendar-of-dates

Learning Outcomes

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

  • ULO1: Apply knowledge of the fundamental molecular properties affecting chemical reactivity and selectivity to predict the products and propose the mechanisms of a range of organic and inorganic reactions.
  • ULO2: Use the primary scientific literature to plan efficient synthetic routes to complex organic and inorganic molecules starting from simple building blocks.
  • ULO3: Assess the risks and hazards associated with working in a synthetic laboratory environment and apply appropriate processes and controls to minimise these risks.
  • ULO4: Employ a set of advanced laboratory techniques to synthesise and purify selected organic and inorganic compounds safely and efficiently.
  • ULO5: Use modern spectroscopic techniques to elucidate the structures of organic and inorganic compounds.
  • ULO6: Communicate experimental observations clearly, concisely and accurately in the form of written scientific reports.

General Assessment Information

 

Late Assessment Submission Penalty

From 1 July 2022, Students enrolled in Session based units with written assessments will have the following university standard late penalty applied. Please see https://students.mq.edu.au/study/assessment-exams/assessments for more information. 

Unless a Special Consideration request has been submitted and approved, a 5% penalty (of the total possible mark) will be applied each day a written assessment is not submitted, up until the 7th day (including weekends). After the 7th day, a grade of '0' will be awarded even if the assessment is submitted. Submission time for all written assessments is set at 11:55 pm. A 1-hour grace period is provided to students who experience a technical concern. 

For any late submission of time-sensitive tasks, such as scheduled tests/exams, performance assessments/presentations, and/or scheduled practical assessments/labs, students need to submit an application for Special Consideration. 

 

Assessments where Late Submissions will be accepted

In this unit, late submissions will accepted as follows: 

  • Laboratory Reports – YES, Standard Late Penalty applies 
  • Workshop Preparation – NO, unless Special Consideration is Granted 

 

Assessment Tasks

Name Weighting Hurdle Due
Workshop Performance 10% No Weeks 1,2,7,12
Practical Classes 35% No Weeks 6,7,8,9,12,13
Mid-Semester Test 15% Yes Week 7
Final Examination 40% No Formal Examination Period

Workshop Performance

Assessment Type 1: Problem set
Indicative Time on Task 2: 5 hours
Due: Weeks 1,2,7,12
Weighting: 10%

 

Workshops consist of interactive problem solving sessions focused on exam-style questions. The workshops are designed to develop independence in problem solving and provide students with an opportunity to ask questions and receive immediate feedback on their work. Students are graded based on their level of preparedness and participation in each workshop.

 
On successful completion you will be able to:
  • Apply knowledge of the fundamental molecular properties affecting chemical reactivity and selectivity to predict the products and propose the mechanisms of a range of organic and inorganic reactions.
  • Use the primary scientific literature to plan efficient synthetic routes to complex organic and inorganic molecules starting from simple building blocks.
  • Use modern spectroscopic techniques to elucidate the structures of organic and inorganic compounds.

Practical Classes

Assessment Type 1: Lab report
Indicative Time on Task 2: 25 hours
Due: Weeks 6,7,8,9,12,13
Weighting: 35%

 

Practical classes with discrete laboratory-based experiments spanning the whole semester. The lab sessions provide advanced practical training in a range of modern synthetic chemistry techniques and allow students to apply the knowledge gained in lectures to solve synthetic challenges safely and efficiently. Students must maintain a laboratory notebook for the duration of the unit, conduct comprehensive risk assessments and produce concise lab reports for the experiments performed.

 
On successful completion you will be able to:
  • Apply knowledge of the fundamental molecular properties affecting chemical reactivity and selectivity to predict the products and propose the mechanisms of a range of organic and inorganic reactions.
  • Use the primary scientific literature to plan efficient synthetic routes to complex organic and inorganic molecules starting from simple building blocks.
  • Assess the risks and hazards associated with working in a synthetic laboratory environment and apply appropriate processes and controls to minimise these risks.
  • Employ a set of advanced laboratory techniques to synthesise and purify selected organic and inorganic compounds safely and efficiently.
  • Use modern spectroscopic techniques to elucidate the structures of organic and inorganic compounds.
  • Communicate experimental observations clearly, concisely and accurately in the form of written scientific reports.

Mid-Semester Test

Assessment Type 1: Quiz/Test
Indicative Time on Task 2: 9 hours
Due: Week 7
Weighting: 15%
This is a hurdle assessment task (see assessment policy for more information on hurdle assessment tasks)

 

A one-hour test covering all material presented in the first half of the unit. The test will consist of a combination of short-answer and mechanism-based questions.

 
On successful completion you will be able to:
  • Apply knowledge of the fundamental molecular properties affecting chemical reactivity and selectivity to predict the products and propose the mechanisms of a range of organic and inorganic reactions.
  • Use modern spectroscopic techniques to elucidate the structures of organic and inorganic compounds.

Final Examination

Assessment Type 1: Examination
Indicative Time on Task 2: 15 hours
Due: Formal Examination Period
Weighting: 40%

 

A three-hour examination covering course material from Weeks 1-13. The examination will assess understanding of all the topics presented within the course and the ability to apply the knowledge gained to solve new problems. The examination will consist of a combination of short-answer and mechanism-based questions.

 
On successful completion you will be able to:
  • Apply knowledge of the fundamental molecular properties affecting chemical reactivity and selectivity to predict the products and propose the mechanisms of a range of organic and inorganic reactions.
  • Use modern spectroscopic techniques to elucidate the structures of organic and inorganic compounds.

1 If you need help with your assignment, please contact:

  • the academic teaching staff in your unit for guidance in understanding or completing this type of assessment
  • the Writing Centre for academic skills support.

2 Indicative time-on-task is an estimate of the time required for completion of the assessment task and is subject to individual variation

Delivery and Resources

Communication

During the semester, the CHEM3601 iLearn site will be used to communicate important information to you. It is your responsibility to regularly check the iLearn site for important announcements and updates

Office Hours

There are no formal office hours for this unit. The teaching staff are happy to receive students outside of the formal lecture, workshop and practical times, but please be aware that we are not always to be found in our offices. It is generally wise to organise an appointment in advance, generally via email (using your university email address).

Recommended Text Books

"Organic Chemistry", 9th Edition (2016) by John McMurry; Cengage Learning (this is the same book as for CHEM2601). Online copies may be available.

"Organic Chemistry", 2nd Edition (2012) by Jonathan Clayden; Oxford University Press. Online copies may be available.

"The Organometallic Chemistry of the Transition Metals", 6th Edition (2014) by Robert H. Crabtree. QD411.8.T73 C73

"Aromatic Heterocyclic Chemistry", (1992) by David T. Davies; Oxford Chemistry Primer QD411.8.T73 C73

"Pericyclic Reactions", (1999) by Ian Fleming; Oxford Chemistry Primer  QD281.R5 F58

"Polar Rearrangements", (1992) by Laurence M. Harwood; Oxford Chemistry Primer QD281.R35.H37/1992

"Introduction to Organic Spectroscopy", (1996) by Laurence M. Harwood and Timothy D. W. Claridge; Oxford Chemistry Primer QD272.S6.H37

"Organometallics 2: Complexes with Transition Metal-Carbon π bonds: (1994) by Manfred Bochmann; Oxford Chemistry Primer. QD411.8.T73 B63 1994 V.2

Suggested Reading for Organometallic Chemistry

"Applied Organometallic Chemistry and Catalysis" (2001) by Robin Whyman; Oxford Chemistry Primer. QD411.W48 2001

"Organometallics 1: Complexes with Transition Metal-Carbon α-bonds" (1994) by Manfred Bochmann; Oxford Chemistry Primer. QD411.8.T73 B63 1994 V.1

Suggested Reading for Spectroscopic Identification of Organic Compounds

“Structural identification of organic compounds with spectroscopic techniques” (2005) Yong-Cheng Ning QD272.S6 N56

“Introduction to spectroscopy: A guide for students of organic chemistry” 2001 Donald L. Pavia, Gary M. Lampman, George S. Kriz QD272.S6.P38 2001

“Practical spectroscopy: The rapid interpretation of spectral data: For McMurry's Organic Chemistry, fifth edition” 2000 Paul R. Young QD95.Y68

Textbooks can be purchased from Booktopia (https://www.booktopia.com.au/).You can also find a number of textbooks with “Organic Chemistry” and "Inorganic Chemistry" in the title in the University library. All cover similar material, but often use different notation. You may find that some of these other books explain certain topics more clearly. There also many web resources, but material placed on the web is not necessarily checked for accuracy, so be careful when using it.

Technology Used and Required

You must regularly check the unit web page for course related information. The web page for this unit can be found at:  http://ilearn.mq.edu.au

Teaching and Learning Strategy

Lectures will be presented as a combination of formal lectures (or recordings of lectures) and interactive Q&A sessions. Historically, non-attendance at lectures has had a significant deleterious effect that is ultimately reflected in poor final exam performance. It is your responsibility to manage your own study/work/life balance.

Class Timetable: Please check http://www.timetables.mq.edu.au for the official timetable of the unit.

Laboratory sessions: You should use the allocated session in Week 1 to familiarise yourselves with the requirements of the practical component of the unit, to watch the essential lab technique videos provided on Echo360 and to complete all relevant prelab exercises, hazard identification and risk assessments for the first experiment. Before commencing each new experiment, you are required to complete the prelab component in your laboratory notebook. This includes completing ALL risk assessments, flowcharts and answering any associated prelab questions. Failure to do so will result in your exclusion from the practical, with consequences for the successful completion of the course. You MUST read each experiment carefully before attending the lab.

Laboratory Reports: Laboratory reports must be submitted through iLearn by the posted due dates. See the Laboratory Manual for full details of what is required.

Unit Schedule

Weeks 1-2 - Organic Spectroscopy (A/Prof. Andrew Piggott)

Weeks 3-4 - Aromaticity and Heterocyclic Chemistry (A/Prof. Andrew Piggott)

Weeks 5-6 - Pericyclic Reactions (Dr Fei Liu)

Week 7 - Mid-Semester Test

Weeks 8-9 - Polar Rearrangements (Dr Fei Liu)

Weeks 10-13 - Organometallic Chemistry (A/Prof. Koushik Venkatesan)

Policies and Procedures

Macquarie University policies and procedures are accessible from Policy Central (https://policies.mq.edu.au). Students should be aware of the following policies in particular with regard to Learning and Teaching:

Students seeking more policy resources can visit Student Policies (https://students.mq.edu.au/support/study/policies). It is your one-stop-shop for the key policies you need to know about throughout your undergraduate student journey.

To find other policies relating to Teaching and Learning, visit Policy Central (https://policies.mq.edu.au) and use the search tool.

Student Code of Conduct

Macquarie University students have a responsibility to be familiar with the Student Code of Conduct: https://students.mq.edu.au/admin/other-resources/student-conduct

Results

Results published on platform other than eStudent, (eg. iLearn, Coursera etc.) or released directly by your Unit Convenor, are not confirmed as they are subject to final approval by the University. Once approved, final results will be sent to your student email address and will be made available in eStudent. For more information visit ask.mq.edu.au or if you are a Global MBA student contact globalmba.support@mq.edu.au

Academic Integrity

At Macquarie, we believe academic integrity – honesty, respect, trust, responsibility, fairness and courage – is at the core of learning, teaching and research. We recognise that meeting the expectations required to complete your assessments can be challenging. So, we offer you a range of resources and services to help you reach your potential, including free online writing and maths support, academic skills development and wellbeing consultations.

Student Support

Macquarie University provides a range of support services for students. For details, visit http://students.mq.edu.au/support/

The Writing Centre

The Writing Centre provides resources to develop your English language proficiency, academic writing, and communication skills.

The Library provides online and face to face support to help you find and use relevant information resources. 

Student Services and Support

Macquarie University offers a range of Student Support Services including:

Student Enquiries

Got a question? Ask us via AskMQ, or contact Service Connect.

IT Help

For help with University computer systems and technology, visit http://www.mq.edu.au/about_us/offices_and_units/information_technology/help/. 

When using the University's IT, you must adhere to the Acceptable Use of IT Resources Policy. The policy applies to all who connect to the MQ network including students.

Changes from Previous Offering

Dr Fei Liu will replace Prof. Peter Karuso for pericyclic reactions and polar rearrangements.

Assessment item weightings have changed slightly.

The mid-semester test is now a hurdle assessment item. A mark of at least 40% is required in the mid-semester test to pass the unit.

Unit information based on version 2022.03 of the Handbook