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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.
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 face to face lectures and tutorials but these will be recorded on Panopto if you are physically unable to attend. We strongly recommend that you attend in person if at all possible to ensure your engagement and success in this course There is also a three hour laboratory session on alternate weeks commencing in paper week 1.
Students who successfully complete the paper 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.
- Be able to apply the above knowledge via synthetic and retrosynthetic analysis to the design of pathways to correctly oriented substituted benzenes.
- 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.
- 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.
- 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.
- Be able to discuss and interpret mechanisms of reactions involving nucleophilic addition to carbonyls involving a variety of substrates and reagents.
- 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.
- 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.
- 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.
- Demonstrate the ability to work safely and competently in the laboratory.
- 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.
- Write concise and clear reports with coherent discussion supported by appropriate referencing and using appropriate language and formatting.
At this stage it is assumed that Test 1 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.
The internal assessment/exam ratio (as stated in the University Calendar) is 60:40. The final exam makes up 40% of the overall mark.
|Percentage of overall mark
11 Aug 2021
|2. Laboratory Report (1)
7 Sep 2021
5 Oct 2021
|4. Laboratory performance (6 sessions)
|5. Laboratory reports (2 & 3)
18 Oct 2021
Required and Recommended Readings
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:
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:
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:
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.
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.
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.
Linkages to Other Papers
This paper is required for a major in chemistry and for BSc (Hons) in chemistry as well as for a major in biochemistry.
Prerequisite papers: CHEM112 or CHEMY102
Restricted papers: CHEM201, CHEM212, CHEM214