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2019/20 Undergraduate Module Catalogue

CHEM2141 Introduction to Organic Synthesis

10 creditsClass Size: 200

Module manager: Prof Steve Marsden
Email: s.p.marsden@leeds.ac.uk

Taught: Semester 1 View Timetable

Year running 2019/20

Pre-requisite qualifications

Level 1 in Chemistry or equivalent

Module replaces

Amendment of current CHEM2141 module. Rebalancing of summative/formative assessment.

This module is not approved as a discovery module

Objectives

1. To equip students with the skills to plan how to prepare organic molecules.
2. To introduce a range of key reactions for application in organic syntheses.
3. To introduce the physical organic concepts that allow the outcome of organic reactions to be rationalised and understood.

Learning outcomes
1. Knowledge of the retrosynthetic approach to planning organic syntheses.
2. Knowledge of key reactions in organic chemistry including substitution reactions of heterocycles, reactions involving enols and enolates.

Skills outcomes
1. Rationalisation of the outcome of organic reactions using mechanistic reasoning
2. Ability to apply retrosynthetic analysis to plan organic syntheses


Syllabus

INTRODUCTORY WORKSHOPS
- Introduction to course; revision of core material from Year 1.

INTRODUCTION TO RETROSYNTHETIC ANALYSIS
Retrosynthesis using Level 1 chemistry.
- Disconnection next to heteroatoms, next to a carbonyl group.
- Revision of addition to and substitution at the carbonyl group, nucleophilic substitution, electrophilic substitution, nucleophilic aromatic
subtsiution. Diazonium chemistry.
- Oxidation (KMnO4) of benzylic substituents, radical bromination of benzylic positions

HETEROCYCLIC CHEMISTRY
- Structure and bonding (pyrrole vs. pyridine); electrophilic substitution of important heterocycles - Structure and bonding (pyrrole vs. pyridine)
- Reactivity relative to benzene: regioselectivity of electrophilic substitution, pKa

INTRODUCTION TO PHYSICAL ORGANIC CHEMISTRY
- The reaction co-ordinate, difference between intermediates and transition states
- Reversible and irreversible reactions: kinetic and thermodynamic control
- Rings: entropic and enthalpic contributions in thermodynamic control of ring size and (kinetic) ring formation. Why is a 4-membered ring so hard to form? Medium rings

ENOLS AND ENOLATES
- Introduction to enols and enolates.
- Enolisation under base and acidic conditions.
- Enolate formation; revision of pKa and choice of base.
- Reactions of enols and enolates: Bromination, alkylation the aldol reaction, Claisen ester condensation, Robinson annelation
- The Michael reaction

Teaching methods

Delivery typeNumberLength hoursStudent hours
Workshop41.004.00
Lectures181.0018.00
Tutorial21.002.00
Private study hours76.00
Total Contact hours24.00
Total hours (100hr per 10 credits)100.00

Private study

76 hours - Revision of lecture notes, preparation for tutorials and examination.

Opportunities for Formative Feedback

Under the new proposal, both tutorials would be formative, one supporting student progress towards the mid-term test on retrosynthesis and a second one supporting student progress towards the January examination on enolate chemistry.

Methods of assessment


Coursework
Assessment typeNotes% of formal assessment
In-course Assessment3 Hour Class Test50.00
Tutorial PerformanceFormative assessment of tutorial work0.00
Tutorial PerformanceFormative assessment of tutorial work0.00
Total percentage (Assessment Coursework)50.00

Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated


Exams
Exam typeExam duration% of formal assessment
Standard exam (closed essays, MCQs etc)1 hr 30 mins50.00
Total percentage (Assessment Exams)50.00

Normally resits will be assessed by the same methodology as the first attempt, unless otherwise stated

Reading list

The reading list is available from the Library website

Last updated: 20/07/2018

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