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
Module version for: 2016/7

Module Convenor: Dr Andrew Russell

Email: a.t.russell@reading.ac.uk

Summary module description:

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.

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:
J E McKendrick (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 (5 lectures) Organic Stereochemistry
This course will continue the discussion of molecular shape and examine the consequence of 2 and 3-dimensional shape upon isomerism to provide a background to the following courses on reactivity at unsaturated and saturated carbon centres.

C D. Smith (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 also 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 regioselective addition of electrophiles to unsymmetrical alkenes will also be discussed and Markovnikov’s rule will be exemplified.

J E McKendrick (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 substitution (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 reactivity. 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:
  Autumn Spring Summer
Lectures 19 20
Seminars 3 3 3
Tutorials 2 3
Guided independent study 63 65 19
       
Total hours by term 87.00 91.00 22.00
       
Total hours for module 200.00

Summative Assessment Methods:
Method Percentage
Written exam 75
Class test administered by School 25

Other information on summative assessment:
Students will attend tutorials and workshop/seminars on the material covered in this module. Attendance is compulsory at both. Both tutorial work and workshop problems are formative in themselves but will form the basis of the summative test held at the beginning of the Spring Term.

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

Submission dates:
Term Test, Week 1 Spring Term
Tutorials to be submitted as detailed on Blackboard.

Formative assessment methods:
Tutorials will allow for focused discussions on topics related to the lecture material and will based around a set of questions the students will prepare answers to before the event.
Workshops are a less formal way for students to work in groups, on set problems, with members of staff present to answer questions.

Penalties for late submission:

For students on chemistry-based degree courses, any unexplained absence from more than two tutorials in chemistry in any term will automatically incur a formal warning from the School Director of Teaching and Learning.
The Module Convenor will apply the following penalties for work submitted late, in accordance with the University policy.
  • where the piece of work is submitted up to one calendar week after the original deadline (or any formally agreed extension to the deadline): 10% of the total marks available for the piece of work will be deducted from the mark for each working day (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: http://www.reading.ac.uk/web/FILES/qualitysupport/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.

    Length of examination:
    2 hours.

    Requirements for a pass:
    A mark of 40% overall.

    Reassessment arrangements:
    Reassessment will be held in August 2016 and will be by examination only worth 100%.

    Additional Costs (specified where applicable):
    1) Required text books:
    2) Specialist equipment or materials:
    3) Specialist clothing, footwear or headgear:
    4) Printing and binding: Students May Wish To Print Out The Notes Provided On Blackboard, This Will Cost 5P Per Sheet In B
    5) Computers and devices with a particular specification:
    6) Travel, accommodation and subsistence:

    Last updated: 21 December 2016

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