CH1OR1-Shape, Structure and Reactivity in Organic Chemistry

Module Provider: Chemistry
Number of credits: 20 [10 ECTS credits]
Level:4
Terms in which taught: Autumn / Spring / Summer module
Pre-requisites:
Non-modular pre-requisites: A level Chemistry or equivalent
Co-requisites: CH1IN1 Fundamentals of Atomic Structure and the Periodic Table CH1PH1 Physical Processes and Molecular Organisation CH1PRA Laboratory Skills for Chemists
Modules excluded: CH1FC1 Fundamental Concepts in Chemistry 1 or CH1FC3 Molecular Studies for the Life Sciences or CH1OR2 Fundamentals of Organic Chemistry or CH1OR4 Further Fundamental Organic Chemistry for Biologists
Current from: 2022/3

Module Convenor: Dr Jessica Gusthart
Email: j.s.gusthart@reading.ac.uk

Type of module:

Summary module description:

This module introduces students to the basic concepts of organic chemistry (to encompass the structure of organic compounds, their isomerism, the concept of a functional group and their predictable reactivity, and the unifying concept of mechanisms) in order to provide the foundation for treatment of the subject in greater depth in later modules or to better appreciate related subjects such as Biochemistry.

Aims:

To introduce students to the basic concepts of organic chemistry (to encompass the structure of organic compounds, isomerism, the concept of a functional group and the unifying concept of mechanisms) in order to provide the foundation for treatment of the subject in greater depth in later modules or to better appreciate related subjects such as Biochemistry.Ìý

Assessable learning outcomes:

Students should be able to:

• Name simple organic compounds and write molecular formulae from given names.


• Draw diagrams of molecules indicating the hybridisation state of individual atoms, showing the disposition of molecular orbitals.


• Draw curved arrow mechanisms for selected organic reactions.


• Assign the stereochemistry of simple organic compounds.


• Explain the mechanisms of substitution and elimination reactions.


• Describe and explain the reactivity of alkenes and alkynes toward a selection of reagents.


• Describe and explain the concept of aromaticity.


• Explain the mechanisms of EAS and NAS reactions.


• Explain the mechanisms of nucleophilic attack upon a variety of carbonyl containing groups.


• Use their knowledge of this fundamental reactivity of organic functional groups to rationalise simple synthetic transformations.

Additional outcomes:
Students will develop proficiency at problem solving.

Outline content:

Atomic structure, orbitals and hybridisation state, electron accounting, drawing structures, representing electron movement, bonding in alkanes, alkenes, alkynes and aromatic molecules, nomenclature, the discussion of molecular shape, isomerism. (8 lectures)

SN1 and SN2 processes, leaving groups and pKa will all be discussed alongside how organic molecules can behave as both electrophiles and nucleophiles in substitution reactions. Synthesis of alkenes via elimination reactions (E1, E2 and E1cB) and reactions that are characteristic of the alkene/alkyne functional groups will be discussed, for example reactions of alkenes with a range of electrophiles, including Br2, HBr, BH3 and m-CPBA. Regioselective addition of electrophiles to unsymmetrical alkenes will also be discussed and Markovnikov’s rule will be exemplified. (8 lectures)

Structure of benzene, the Hückel rule for aromaticity and the stability of aromatic molecules. Electrophilic aromatic substitution (EAS) and nucleophilic aromatic substitution (NAS), structure and reactivity of benzyne. The significance of substituents on the regiochemistry of these reactions will be discussed. Additionally, the synthesis and reactions of diazoaromatics will be covered. (8 lectures)

Structure and bonding of the carbonyl functional group, including the link between structure and reactivity. The reactions of carbonyl groups with nucleophiles and reducing agentsand the chemistry of carboxylic acids, esters and amides. (5 lectures)

Brief description of teaching and learning methods:

Two one-hour lectures per week with approximately one tutorial every three weeks. Summer seminars are scheduled for revision.

Summative assessment- Examinations:

A two-hour examination during the Summer Term based upon lecture and tutorial material. 75%

The examination for this module will require a narrowly defined time window and is likely to be held in a dedicated exam venue.

Summative assessment- Coursework and in-class tests:

One-hour closed book examination at the beginning of the Spring Term based upon lecture and tutorial material. 25%

Formative assessment methods:

Students will attend tutorials and workshop/seminars on the material covered in this module. Tutorials will allow for focused discussions on topics related to the lecture material and will be based around a set of questions the students will prepare answers to before the event. During the workshop/seminars, students will work on set problems with members of staff present to give guidance and feedback. Attendance is compulsory at all of these events.

Submission dates:



Term Test, Week 2 Spring Term

Penalties for late submission:

Students will attend tutorials on the material covered in this module. Tutorials will allow for focused discussions on topics related to the lecture material and will be based around a set of questions the students will prepare answers to before the event. Attendance is compulsory.

Submission dates:



Tutorials to be submitted as detailed on Blackboard.

Assessment requirements for a pass:
A mark of 40% overall.

Reassessment arrangements:

Reassessment will be held in the resit period and will be by examination only, worth 100%.

Additional Costs (specified where applicable):

1) Required text books:ÌýÌý

2) Specialist equipment or materials:ÌýÌý

3) Specialist clothing, footwear or headgear:ÌýÌý

4) Printing and binding:ÌýÌý

5) Computers and devices with a particular specification:ÌýÌý

6) Travel, accommodation and subsistence:ÌýÌý

Last updated: 22 September 2022