CH1OR1NU-Shape, Structure and Reactivity in Organic Chemistry (NUIST)

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:
Co-requisites:
Modules excluded:
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.

Assessable learning outcomes:

Students should be able to:

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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 reactiv ity 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:

Foundations of Organic Chemistry and Nomenclature (3 lectures and 1 workshop): Atomic structure, orbitals and hybridisation state, electron accounting, drawing structures, representing electron movement, bonding in alkanes, alkenes, alkynes and aromatic molecules, nomenclature.

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Organic Stereochemistry (2 lectures and 1 workshop): This course will continue the discussion of molecular shape and examine the consequence of 2 and 3-dimensional shape u pon isomerism to provide a background to the following courses on reactivity at unsaturated and saturated carbon centres.

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Substitution and Elimination Reactions (10 lectures and 2 workshops): 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 reactio ns. 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.

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Reactivity of Unsaturated Compounds (4 lectures and 1 workshop): 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 an d m-CPBA will be described. The regioselective addition of electrophiles to unsymmetrical alkenes will also be discussed and Markovnikov’s rule will be exemplified.

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Aromatic Chemistry (9 lectures and 2 workshops): 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.

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An Introduction to Carbonyl Group Chemistry (11 lectures and 2 workshops): We will consider the structure and bonding of the carbonyl functional group, its fundamenta l 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.

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2 Review Workshops: Revision of material covered in all courses in preparation for the final examination.

Brief description of teaching and learning methods:

Each lecture takes two hours and a two-hour workshop is generally provided for each unit. The lecture may also discuss the synthetic skills needed to apply the module materials in simple organic compound synthesis. At a workshop for each module is provided for students to work together and for the lecturer to answer questions.

Contact hours:

Ìý	Autumn	Spring	Summer
Lectures	38	40
Seminars	10	12
Guided independent study:	Ìý	Ìý	Ìý
Ìý Ìý Revision and preparation	52	48
Ìý	Ìý	Ìý	Ìý
Total hours by term			0
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:

One two-hour examination at the end of each semester (= 2 × 2h overall) based upon lecture, tutorial and workshop material. (2 × 37.5% = 75%)

Summative assessment- Coursework and in-class tests:

One one-hour closed-book in-class test in the middle of each semester (= 2 × 1h overall) based upon lecture, tutorial and workshop material. (2 × 12.5% = 25%)

Formative assessment methods:

Students will attend tutorials/workshops 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 work on set problems with members of staff present to give guidance and feedback.

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 twice a year in March 2020 and August 2020 and will be by examination only, with each exam worth 50%.

Additional Costs (specified where applicable):

Last updated: 4 April 2020