CHEMY201-20B (HAM)

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)

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: cheryl.ward@waikato.ac.nz

You can contact staff by:

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Paper Description

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This paper covers aspects of organic chemistry including reaction mechanisms with carbanion and radical intermediates, mechanisms of reactions of carbonyl groups, multiple electrophilic substitutions of aromatic rings and an introduction to carbohydrate chemistry.

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Paper Structure

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Lecture Notes

Printed workbooks can be obtained from Waikato Print https://www.waikato-print.co.nz/students/ or download and print the workbook 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.

The course consists of both online and face to face components. We believe that the face to face sessions are the best way to ensure your engagement in this course but you will have the option of participating in these via Zoom if you are physically unable to attend. There is also a three hour laboratory session on alternate weeks commencing in paper week 1.

For MICHELE'S section of the course:

Up to three face to face sessions per week will be used in a flexible manner as workshops or tutorials as appropriate. The lecture material will also be available online in the form of Panopto recordings. This is not to be regarded as a substitute for attending the face to face sessions but can be used for you to read in advance of sessions, if you are physically unable to come to class or as revision. Michele will indicate what is happening in a particular week as she goes along but nominally there will be two workshops plus a tutorial (zoom or in person).

For MERILYN'S section of the course:

Each week you should view the two recordings indicated for the week in the detailed timetable below, which is also reproduced on Moodle. As you view the recording you should complete the relevant section of your workbook of notes. Printed workbooks can be obtained from Waikato Print https://www.waikato-print.co.nz/students/ or download and print the workbook from Moodle. The scheduled Thursday workshop will be a face to face session during which questions can be answered and problems relevant to the weeks work will be practiced. For those unable to attend on Thursday the same content will be repeated as a Zoom workshop during the scheduled Monday workshop the following week.

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Learning Outcomes

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Students who successfully complete the course should be able to:

  • 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.
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  • Be able to apply the above knowledge via synthetic and retrosynthetic analysis to the design of pathways to correctly oriented substituted benzenes.
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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.
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  • 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.
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  • 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.
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  • Be able to discuss and interpret mechanisms of reactions involving nucleophilic addition to carbonyls involving a variety of substrates and reagents.
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  • 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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  • 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.
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  • 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.
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  • Demonstrate the ability to work safely and competently in the laboratory.
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  • 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.
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  • Write concise and clear reports with coherent discussion supported by appropriate referencing and using appropriate language and formatting.
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Assessment

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Assessment Components

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The internal assessment/exam ratio (as stated in the University Calendar) is 100:0. There is no final exam. The final exam makes up 0% of the overall mark.

The internal assessment/exam ratio (as stated in the University Calendar) is 100:0 or 0:0, whichever is more favourable for the student. The final exam makes up either 0% or 0% of the overall mark.

Component DescriptionDue Date TimePercentage of overall markSubmission MethodCompulsory
1. Test
12 Aug 2020
12:00 PM
17.5
  • In Class: In Workshop
2. Laboratory Report (1)
7 Sep 2020
4:30 PM
6.67
  • Email: Lecturer
  • Hand-in: In Lab
3. Assignment
5 Oct 2020
4:30 PM
17.5
  • Email: Lecturer
  • Hand-in: In Lab
4. Laboratory performance (6 sessions)
5
5. Laboratory reports (2 & 3)
19 Oct 2020
4:30 PM
13.33
  • Online: Submit through Moodle
6. Final Test
40
  • Online: Submit through Moodle
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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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, 7th or 8th 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/

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Recommended Readings

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Recommended reading for organic chemistry: The book Fessenden: Organic chemistry is a particularly valuable reference for reaction mechanisms and aromatic substitution; a number of copies of this are available in Course Reserve. 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; note that the more recent editions will refer to more modern techniques.

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Online Support

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Incomplete lecture notes for Organic Chemistry are accessible on Moodle from where they should be downloaded and printed in advance for completion during lectures. If printing off Moodle make sure the notes are full size to allow for copious annotation; please be sure to keep these in an organised state. Questions about course work may be directed to lecturers either via email or via moodle. All lectures are recorded on Panopto and are available on moodle, which is useful for review or catching up. We STRONGLY recommend, when possible, attendance at lectures.

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Workload

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Total: 150 hours

Formal contact hours: 24 Lectures (@50 minutes), 18 hours of laboratory work plus a maximum of 12 tutorials (@ 50 minutes).

Personal study: 3 hours per lecture minimum during the semester for reviewing material and undertaking problem sets; 3 laboratory reports at 8 hours per report including report writing and acquisition of spectra.

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Linkages to Other Papers

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This paper is required for a major in chemistry and for BSc (Hons) in chemistry as well as for a major in biochemistry.

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Prerequisite(s)

This paper requires students to attend some in-person laboratory or fieldwork. It can not be taken solely online. Do you still want to choose this paper? Prerequisite papers: CHEM112 or CHEMY102

Corequisite(s)

Equivalent(s)

Restriction(s)

Restricted papers: CHEM201, CHEM212, CHEM214

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