CHEMY201-23B (HAM)

Organic Chemistry

15 Points

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The University of Waikato
Academic Divisions
Division of Health Engineering Computing & Science
School of Science
Chemistry and Applied Physics

Staff

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Convenor(s)

Michele Prinsep

Michele Prinsep
9392
E.3.06
See Moodle
michele.prinsep@waikato.ac.nz

Lecturer(s)

Ben Dickson

Ben Dickson
4188
CD.3.01
See Moodle
benjamin.dickson@waikato.ac.nz

Administrator(s)

Placement/WIL Coordinator(s)

Tutor(s)

Student Representative(s)

Lab Technician(s)

Librarian(s)

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:
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What this paper is about

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Welcome to CHEMY201-23B Organic Chemistry

Special Notice About Attendance And Participation
CHEMY201, Organic Chemistry is likely one of the more challenging papers that you will undertake at university. To ensure a successful outcome for
students, we strongly advise you to attend lectures in person if you possibly can. We will be monitoring engagement closely, in addition to the usual recording of attendance at laboratory classes.

Monitoring of Engagement will entail:
ꞏ Attendance will be taken at lectures and tutorials.
ꞏ Viewing statistics on Panopto recordings will be monitored weekly.
If you are unable to attend one or more sessions for an important reason, for example sickness or childcare responsibilities, please notify the lecturer, by Email and viewing of the Panopto recording will be taken as a proxy for your attendance on that occasion.

If you repeatedly fail to attend sessions or view the corresponding recording, you can expect that we will contact you and a note may be
made on your MyWaikato record indicating your lack of participation. Such notes may impact on any future requests to enrol.

PAPER DESCRIPTION
This 15 point paper builds upon the subject matter covered In CHEMY102 and covers aspects of theoretical and practical organic chemistry including multiple electrophilic substitutions of aromatic rings, an introduction to carbohydrate chemistry, reaction mechanisms with carbanion and radical intermediates and mechanisms of reactions of carbonyl groups.

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How this paper will be taught

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This paper consists of lectures, tutorials as required and a laboratory course which gives students a chance to understand practical aspects of the techniques covered.

The course has three timetabled lecture slots per week. Usually one of these would be used in a tutorial manner or for tests as required, but in some weeks, the tutorial slot will be used to deliver lecture material due to public holidays affecting lecture slots and to accommodate timetable clashes for staff. There is also a three hour laboratory session on alternate weeks commencing in paper week 1.

Note that the actual number of lab streams offered will depend on the number of students enrolled in the course.

The tutorial day is nominally Wednesday but this may need to vary this from time to time to suit the schedule of individual lecturers and as stated above, will be used as a lecture slot as required.

Please note that the test is held in a lecture slot (Wednesday).

Further details about the test, including coverage, will be announced via Moodle in due course.

A detailed schedule of events is listed later in the outline.

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Required Readings

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For all organic chemistry courses (CHEMY102, 201 and 301) there is only one text, which is Brown, Iverson, Anslyn, Foote: Organic Chemistry, 8th or 9th edition. This may be purchased from Campus Books Ltd. An electronic or hardback version may be purchased at:

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

You should be aware that the electronic versions may only remain current for five years.

If you have problems with electron diagrams and keeping track of electrons in organic chemistry mechanisms, we strongly recommend the book “Pushing Electrons: A guide for Students of Organic Chemistry” by Weeks & Winter published by Cengage Learning. An electronic or hardback version may be purchased at:

https://www.cengagebrain.co.nz/shop/9781285671666

For all Cengage purchases you receive a discount for purchase through the website using the discount code NZ15OFF

Note that the library web page has guidance for accessing and creating reading lists for University of Waikato courses:

https://www.waikato.ac.nz/library/reading-lists/

Recommended reading for organic chemistry:

The book Fessenden: Organic chemistry is a particularly valuable reference for reaction mechanisms and aromatic substitution. Other general organic texts of which there are a number in the library, will be useful for reference and backup.
For assistance with spectral interpretation we recommend Silverstein, Webster, Kiemle & Bryce: Spectrometric Identification of Organic Compounds; 8th edition. Wiley. There are a number of earlier editions of this book in the library all with Silverstein as the lead author but with various other authors.

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Learning Outcomes

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Students who successfully complete the course should be able to:

  • Be able to apply the above knowledge via synthetic and retrosynthetic analysis to the design of pathways to correctly oriented substituted benzenes
    Linked to the following assessments:
  • Be able to convert acyclic monosaccharides to the various ring forms with correct anomeric configuration and equally open a ring form to the corresponding acyclic structure. Be able to predict the products of reactions of the anomeric centre
    Linked to the following assessments:
  • Be able to discuss and interpret mechanisms of reactions involving nucleophilic addition to carbonyls involving a variety of substrates and reagents
    Linked to the following assessments:
  • Be able to discuss and interpret the mechanisms of a wide range of (apparently disparate) reaction types in terms of the unifying concept of stabilisation of carbanion reaction intermediates
    Linked to the following assessments:
  • Be able to explain trends in reactivity and pKa due to inductive & resonance effects & be able to recognise the most likely type of intermediate from reagents, reaction conditions & products and derive mechanisms as part of the explanation for reactivity
    Linked to the following assessments:
  • Be able to predict the position of subsequent substitutions of mono-substituted benzene and explain rates and directive effects in terms of intermediate carbocation stabilisation for mono-and further substituted benzenes
    Linked to the following assessments:
  • Be able to produce mechanisms with simple reactants showing the course of all the reactions outlined above and apply these mechanisms to more complex molecular reactants and utilize these reactions to synthesize a specified product
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  • Be able to reproduce mechanisms for a variety of reactions involving radical intermediates and discuss and interpret reactions involving radicals in terms of structure and relative stabilities
    Linked to the following assessments:
  • Demonstrate familiarity with the terminology of monosaccharide sugars including number of carbons & functional group, D or L configuration, ring size & alpha & beta anomeric configurations & identify a disaccharide sugar as reducing or non-reducing
    Linked to the following assessments:
  • Demonstrate the ability to carry out a multi-step organic synthesis under direction and characterise the product by GC and/or HPLC, IR and NMR as required
    Linked to the following assessments:
  • Demonstrate the ability to work safely and competently in the laboratory
    Linked to the following assessments:
  • Write concise and clear reports with coherent discussion supported by appropriate referencing and using appropriate language and formatting
    Linked to the following assessments:
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Assessments

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How you will be assessed

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

These items will NOT be open-book.

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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. Test
16.5
  • In Class: In Lecture
2. Laboratory Report (1)
5 Sep 2023
4:30 PM
7
  • Email: Lecturer
  • Hand-in: In Lab
✔
3. Assignment
9 Oct 2023
4:30 PM
18.5
  • Online: Submit through Moodle
4. Laboratory performance (6 sessions)
4
5. Laboratory reports (2 & 3)
16 Oct 2023
4:30 PM
14
  • Online: Submit through Moodle
6. 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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