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 or
Current from: 2020/1

Module Convenor: Dr Andrew Russell

Email: a.t.russell@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:

L M Harwood (8 lectures) Foundations of Organic Chemistry and Nomenclature

Atomic structure, orbitals and hybridisation state, electron accounting, drawing structures, representing electron movement, bonding in alkanes, alkenes, alkynes and aromatic molecules, nomenclature.



A T Russell (6 lectures) Organic Stereochemistry

This course will continue the discussion of molecular shape and examine the consequence of 2 and 3-dimensional shape upon is omerism to provide a background to the following courses on reactivity at unsaturated and saturated carbon centres.



F J Davis (6 lectures) Substitution and Elimination Reactions

This course will examine nucleophilic substitution reactions, SN1, SN2 and SNi processes, leaving groups and pKa, and neighbouring group participation. We will discuss how organic molecules can behave as both electrophile and nucleophile in substitution reactions. This course will als o consider the synthesis of alkenes via elimination reactions (E1, E2 and E1cB) and will seek to delineate why, in a given situation, elimination or substitution reactions predominate.



L M Harwood (4 lectures) Reactivity of Unsaturated Compounds

We will study reactions that are characteristic of the alkene/alkyne functional groups. For example, reactions of alkenes with a range of electrophiles, including Br2, HBr, BH3 and m-CPBA will be described. The regios elective addition of electrophiles to unsymmetrical alkenes will also be discussed and Markovnikov’s rule will be exemplified.



P. B. Cranwell (8 lectures) Aromatic Chemistry

We will study the structure of benzene, the Hückel rule for aromaticity and the stability of aromatic molecules. The reactivity of these compounds will be considered under the general mechanistic headings; electrophilic aromatic substitution (EAS) and nucleophilic aromatic subs titution (NAS) as well as the 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.



A T Russell (8 lectures) An Introduction to Carbonyl Group Chemistry

We will consider the structure and bonding of the carbonyl functional group, its fundamental modes of reactivity including the link between structure and rea ctivity. The reactions of carbonyl groups with nucleophiles and reducing agents will be covered together with methods of formation, methods of removal and the chemistry of carboxylic acids, esters and amides.



All Staff: 3 Review Workshops

Revision of material covered in all courses in preparation for the final examination.

Brief description of teaching and learning methods:
Two one-hour lectures per week with approximately one tutorial and one workshop/seminar every three weeks. Summer seminars are scheduled for revision.

Contact hours:

Ìý	Autumn	Spring	Summer
Lectures	20	20
Seminars	3	3	3
Tutorials	2	3
Guided independent study:	62	65	19
Ìý	Ìý	Ìý	Ìý
Total hours by term	87	91	22
Ìý	Ìý	Ìý	Ìý
Total hours for module	200

Summative Assessment Methods:

Method	Percentage
Written exam	75
Class test administered by School	25

Summative assessment- Examinations:

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

Summative assessment- Coursework and in-class tests:

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

Submission dates:

Term Test, Week 2 Spring Term

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:

Tutorials to be submitted as detailed on Blackboard.

Penalties for late submission:

The Module Convenor will apply the following penalties for work submitted late:

• 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[1] (or part thereof) following the deadline up to a total of five working days;
• where the piece of work is submitted more than five working days after the original deadline (or any formally agreed extension to the deadline): a mark of zero will be recorded.

The University policy statement on penalties for late submission can be found at:
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.

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

Reassessment arrangements:

Reassessment will be held in August 2019 and will be by examination only, worth 100%.

Additional Costs (specified where applicable):

Last updated: 4 April 2020