CHEMY301-21A (HAM)

Advanced Organic Chemistry

15 Points

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Division of Health Engineering Computing & Science
School of Science
Chemistry and Applied Physics

Staff

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Convenor(s)

Lecturer(s)

Administrator(s)

Placement/WIL Coordinator(s)

Tutor(s)

Student Representative(s)

Lab Technician(s)

Librarian(s)

: cheryl.ward@waikato.ac.nz

You can contact staff by:

  • Calling +64 7 838 4466 select option 1, then enter the extension.
  • Extensions starting with 4, 5, 9 or 3 can also be direct dialled:
    • For extensions starting with 4: dial +64 7 838 extension.
    • For extensions starting with 5: dial +64 7 858 extension.
    • For extensions starting with 9: dial +64 7 837 extension.
    • For extensions starting with 3: dial +64 7 2620 + the last 3 digits of the extension e.g. 3123 = +64 7 262 0123.
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Paper Description

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This paper covers theoretical and practical Organic Chemistry and is regarded as an extension of the principles learnt in CHEMY102 and CHEMY201. This paper supports the major in chemistry and the minor in biochemistry.

The theory section of this paper (12 x 2 Lectures per week plus tutorials as required) covers advanced carbohydrate chemistry, principles of chemical synthesis, pericyclic reactions and natural product chemistry.

In the laboratory sessions (6 x 3 hours per week in one 6 week block) you will synthesize two compounds and characterize them and carry out a multi-step reaction preparing glucose derivatives with characterization.

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Paper Structure

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The course consists of two formal lectures per week plus a tutorial. In some weeks the tutorial slot may be used to deliver lecture material due to public holidays affecting lecture slots and to accommodate timetable clashes for staff.

Tutorials may not always occur each week.

Lectures and tutorials are recorded on Panopto and are available through Moodle.

Lecture Notes

These must be purchased from Campus Copy or downloaded from Moodle. We recommend that you print these notes single-sided to allow space for extra writing and also print them large enough to allow annotation of figures and chemical structures.

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Learning Outcomes

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Students who successfully complete the paper should be able to:

  • Explain pericyclic reactions and sigmatropic shifts in terms of frontier molecular orbital theory
    Linked to the following assessments:
  • Predict stereochemistry of products of pericyclic reactions using Woodward-Hoffmann rules.
    Linked to the following assessments:
  • Suggest synthetic pathways to mono and bicyclic compounds using pericyclic reactions
    Linked to the following assessments:
  • Explain equilibrium distributions of ring forms of monosaccharides in terms of stereoelectronic influences
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  • Name common biological oligosaccharides
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  • Use the disconnection approach to suggest synthons for synthesis of target molecules using reactions learned at all three levels.
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  • Comment on the efficacy of a synthesis in terms of atom economy
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  • Comment on aspects of chemoselectivity in a synthesis and the use of protecting groups
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  • Draw/indicate the precursors and a plausible biosynthetic route to the production of a given secondary metabolite.
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  • Analyse secondary metabolites and recognise their biosynthetic pathway of origin.
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  • Analyse provided experimental labeling information to predict likely biosynthetic routes to a given metabolite.
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  • Explain the differences between stable and radioactive labels and the relative merits of each.
    Linked to the following assessments:
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Assessment

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Please note that Laboratory Report 1 is a compulsory piece of assessment.

At this stage it is assumed that the test and the final test or examination will occur on campus and in person.

These items will NOT be open-book.

In the event of a lockdown preventing in person assessment, each assessment item will be replaced by a 50:50 mark split between an online open-book written assessment and an individual oral examination; the latter will NOT be open-book. In the event that your mark for the oral assessment is significantly lower than your mark for the written assessment, you will have an opportunity to sit a second oral assessment and if there continues to be a disparity between your performance in the two parts of the assessment you will be required to undertake an in-person written test. In the event that the oral examination occurs via Zoom or some similar program, you will be required to have video operating, to look at the camera during the examination and to have your hands in view. If you do not operate with video, you will be deemed not to have undertaken the oral assessment item.

In 2020, a significant number of suspected cases of cheating were discovered, in which students were found to have used online answer services from a company, so-called "contract cheating". Do not be tempted to use these 'services', despite their apparent low fees and promises of fast turnaround times. They breach the University's code of conduct on academic integrity. Answers provided by such services have been found to have issues including chemical errors, inappropriate high levels of detail, and/or poor grammar and spelling, making them stand out to the experienced and trained eyes that belong to your lecturers. If you are suspected of cheating in any way, your assessment item(s) will be immediately referred to the Discipline Committee for investigation. If you are found guilty of cheating, there will be a penalty proportionate to the severity of your offending. If your career requires that you apply for membership of a professional body, you may be required to disclose any such misconduct investigation.

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Assessment Components

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The internal assessment/exam ratio (as stated in the University Calendar) is 60:40. There is no final exam. The final exam makes up 40% of the overall mark.

The internal assessment/exam ratio (as stated in the University Calendar) is 60:40 or 0:0, whichever is more favourable for the student. The final exam makes up either 40% or 0% of the overall mark.

Component DescriptionDue Date TimePercentage of overall markSubmission MethodCompulsory
1. Assignment 1: Advanced Carbohydrate Chemistry
29 Mar 2021
4:30 PM
8
  • Email: Lecturer
2. Assignment 2: Synthetic Strategies
27 Apr 2021
4:30 PM
8
  • Email: Lecturer
3. Test: Pericyclic Reactions & Natural Products
2 Jun 2021
10:00 AM
16
  • Hand-in: In Lecture
4. Laboratory Performance
4
5. Laboratory Report 1
22 Mar 2021
4:30 PM
8
  • Hand-in: In Lab
6. Laboratory Report 2
19 Apr 2021
4:30 PM
8
  • Email: Lecturer
7. Laboratory Report 3
19 Apr 2021
4:30 PM
8
  • Email: Lecturer
8. Exam
40
Assessment Total:     100    
Failing to complete a compulsory assessment component of a paper will result in an IC grade
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Required and Recommended Readings

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Recommended Readings

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Organic chemistry:

For all organic chemistry courses (CHEMY102, 201 and 301) there is only one text, which is Brown, Iverson, Anslyn, Foote: Organic Chemistry, 7th or 8th edition. This may be purchased from Campus Books Ltd. An electronic version may be purchased at:

https://www.cengagebrain.co.nz/shop/isbn/9781305580350

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Online Support

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This paper has a Moodle page (http://elearn.waikato.ac.nz) where you will be able to access lecture material, problem sets with answers etc. There are also discussion forums where you can both ask and answer questions. All lectures are recorded via Panopto and are available through Moodle.

PLEASE NOTE: Moodle will be used for class notices etc and it is your responsibility to regularly check the site and your appropriate e-mail account. Instructions provided on Moodle and during lectures are considered to be given to the class as a whole.


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Workload

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150 hours total comprised of lectures (tutorials do not always occur), laboratory classes plus study, laboratory reports and assignments.
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Linkages to Other Papers

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This paper is strongly recommended for the majors in Chemistry, Molecular Biology including Biochemistry, and Materials Science.
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Prerequisite(s)

Prerequisite papers: CHEMY201 or CHEM212 and CHEM214

Corequisite(s)

Equivalent(s)

Restriction(s)

Restricted papers: CHEM301, CHEM312, CHEM314.

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