CH4AO1: Advanced Topics in Organic Chemistry

Module code: CH4AO1

Module provider: Chemistry; School of Chemistry, Food and Pharmacy

Credits: 20

Level: Level 4 (Undergraduate Masters)

When you'll be taught: Semester 1

Module convenor: Dr Chris Smith, email: c.d.smith@reading.ac.uk

Module co-convenor: Dr Jessica Gusthart, email: j.s.gusthart@reading.ac.uk

Pre-requisite module(s): BEFORE TAKING THIS MODULE YOU MUST TAKE CH2OR1 (Compulsory)

Co-requisite module(s):

Pre-requisite or Co-requisite module(s):

Module(s) excluded:

Placement information: NA

Academic year: 2024/5

Available to visiting students: Yes

Talis reading list: Yes

Last updated: 17 June 2024

Overview

Module aims and purpose

This course will introduce the most up-to-date techniques for controlling chirality in the synthesis of complex molecular targets and study the chemistry of heterocycles with more than one heteroatom. Both topics build on the basics of organic chemistry that you have learnt during the first three years of your degree and the group problem solving. This course should be useful to anyone planning to pursue a chemistry-related career in the future. 

Module learning outcomes

By the end of the module, it is expected that students will be able to:

1. Describe the processes through which one enantiomer of a given molecular target may be synthesised.
2. Explain and apply selected methods of asymmetric synthesis to unseen synthetic problems.
3. Describe the synthesis and properties of heterocyclic compounds and apply the knowledge to aid an understanding of their role in biological systems.
4. Demonstrate an ability to plan a synthesis to deliver a range of compounds for a drug discovery programme and to communicate it in oral and written form.

Module content

The Elements of Asymmetric Synthesis. This course will examine the general principles underlying asymmetric synthesis. In particular we will examine the need to generate diastereoisomeric transition states in order to achieve asymmetric induction. We will examine the relative merits of chiral auxiliaries and chiral catalysts then exemplify these with reactions of great synthetic significance, e.g. the Evans enolate alkylation. (10 lectures) 

Advanced Heterocyclic Chemistry (5 hours). Chemistry and synthesis of complex heteroaromatics: pyridazines, pyrazines, pyrimidines, imidazoles, thiazoles and oxazoles. Complex heteroaromatics in Nature. 

Synthesis in Medicinal Chemistry (10 workshops) – In this part of the course the class will be split into teams and each team assigned a synthetic, medicinal chemistry task. The team will be charged with completing the task set through appropriate division of labour. The problem will rely heavily on synthetic chemistry and the students’ ability to research the literature, taking advantage of databases such as Reaxys and SciFinder.  

Structure

Teaching and learning methods

Lectures and workshops will be used to deliver learning content. A group-based problem solving exercise will help to understand how a medicinal chemist applies synthetic organic chemistry to the development of a drug. This will be supported as a series of workshops. 

Study hours

At least 31 hours of scheduled teaching and learning activities will be delivered in person, with the remaining hours for scheduled and self-scheduled teaching and learning activities delivered either in person or online. You will receive further details about how these hours will be delivered before the start of the module.

Please note the independent study hours above are notional numbers of hours; each student will approach studying in different ways. We would advise you to reflect on your learning and the number of hours you are allocating to these tasks.

Semester 1 The hours in this column may include hours during the Christmas holiday period.

Semester 2 The hours in this column may include hours during the Easter holiday period.

Summer The hours in this column will take place during the summer holidays and may be at the start and/or end of the module.

Assessment

Requirements for a pass

Students need to achieve an overall module mark of 50% to pass this module.

Summative assessment

Penalties for late submission of summative assessment

The Support Centres will apply the following penalties for work submitted late:

Assessments with numerical marks

• where the piece of work is submitted after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for that piece of work will be deducted from the mark for each working day (or part thereof) following the deadline up to a total of three working days;
• the mark awarded due to the imposition of the penalty shall not fall below the threshold pass mark, namely 40% in the case of modules at Levels 4-6 (i.e. undergraduate modules for Parts 1-3) and 50% in the case of Level 7 modules offered as part of an Integrated Masters or taught postgraduate degree programme;
• where the piece of work is awarded a mark below the threshold pass mark prior to any penalty being imposed, and is submitted up to three working days after the original deadline (or any formally agreed extension to the deadline), no penalty shall be imposed;
• where the piece of work is submitted more than three working days after the original deadline (or any formally agreed extension to the deadline): a mark of zero will be recorded.

Assessments marked Pass/Fail

• where the piece of work is submitted within three working days of the deadline (or any formally agreed extension of the deadline): no penalty will be applied;
• where the piece of work is submitted more than three working days after the original deadline (or any formally agreed extension of the deadline): a grade of Fail will be awarded.

The University policy statement on penalties for late submission can be found at: /cqsd/-/media/project/functions/cqsd/documents/qap/penaltiesforlatesubmission.pdf

You are strongly advised to ensure that coursework is submitted by the relevant deadline. You should note that it is advisable to submit work in an unfinished state rather than to fail to submit any work.

Formative assessment

Formative assessment is any task or activity which creates feedback (or feedforward) for you about your learning, but which does not contribute towards your overall module mark.

Students will attend tutorials on the lecture material covered in this module. Attendance is compulsory. Tutorials to be submitted as detailed on Blackboard. Revision sessions before the exams. 

Feedback in workshops to assist with a team chemical synthesis problem.  

Reassessment

Additional costs