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CHEM1032 Fundamentals of Organic Chemistry II

Module Overview

Aims and Objectives

Module Aims

The aims of the module are: The aim of this course is to provide a core for future studies in chemistry and allied subjects, in aspects of Organic Chemistry as specified below and an introduction to basic practical skills including safe working practices (risk, hazard and control measures), laboratory report writing (written and verbal communication of results), error and accuracy. Teaching in this course recognises the diversity of our intake in terms of A level syllabus followed and choice of non-Chemistry A level subjects (maths, physics, etc.). Theory component: The aim of this organic chemistry course is to introduce students to many of the key concepts of organic chemistry through a survey of the basic reactions of selected monofunctional aliphatic and aromatic molecules. Particular emphasis is placed on the underlying mechanistic pathways that are involved together with some of their stereochemical consequences. The application of spectroscopic techniques for the determination of molecular structure is also considered. Hence, the course seeks to establish a sound foundation on which further learning in organic chemistry can built. Practical component: The aim of the practical component of the module is to provide students with the skills that will be needed in their future practical work. Instruction is provided regarding the in the presentation of practical reports, awareness of health and safety procedures, practical skills in the laboratory (and the theory on which they are based) and problem solving in the practical situation. During the first semester some of this instruction will take place in Seminars that precede the practical classes. Students will undertake as series of four experiments, of which the titles below are examples: • Grignard reaction • Aromatic substitution • Siloxanes • Enzymatic hydrolysis Each experiment is also preceded by a prelaboratory exercise that involves a combination of audio visual resources, accessible via Blackboard, that will help prepare you for the experimental work. A short quiz based on this content is to be completed before starting practical work. There are separate learning outcomes for each experiment and these are further specified in the practical scripts.

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

  • Recognise many functional groups and their reactivity
  • Set up glassware and apparatus to conduct experiments in Organic Chemistry.
  • Interpret data from a range of physical techniques to characterise Organic componds.
  • Present the results of a practical investigation in a concise manner.
  • Recognise many fundamental bond forming reactions and how to apply them in synthesis
  • Describe bonding models and appreciate how these impact on the properties of a simple molecule
  • Apply curly arrow nomenclature to depict the mechanistic course of a reaction
  • Appreciate when different reactions are likely to compete and ways to bias reactions towards a single outcome
  • Understand and apply the concept of protecting groups
  • Understand how spectroscopic techniques can be used to delineate a molecule’s structure
  • Understand the influence of bond polarisation on a molecule’s structure and reactivity
  • Evaluate the risks associated with an experiment and understand how to mitigate against those risks.

Syllabus

Applications of nucleophilic substitution reactions: Synthetic value of reactions of alkyl halides and sulfonates with nucleophiles. Revision of key features of SN1 and SN2 reaction mechanisms (including allylic and benzylic systems). Formation of alcohols by hydrolysis of alkyl halides. Reactions of alcohols with strong acids e.g. reaction with HX to form alkyl halides and dehydration to give alkenes. Use of thionyl chloride and phosphorous pentabromide to form alkyl halides (including mechanisms). Use of nitrogen, sulfur and phophorus nucleophiles. Organometallic reagents for C-C bond formation: the chemistry of Grignard reagents (reversal of polarisation at carbon). Formation by reaction with alkyl halides – reaction conditions. Grignards as bases (reactions with water, alcohols and alkynes). The elimination reactions: Substitution vs elimination in alkyl halides. Dehydration of alcohols. Elimination mechanisms (E1, E2 and E1cb). Stereochemistry and regioselectivity in elimination reactions. Electrophilic additions to alkenes: addition to alkenes of hydrogen halides, including regio- and stereochemistry for Markovnikov and anti-Markovnikov additions. Bromination of alkenes via a bromonium ion leading to the formation of trans-1,2-dibromides and bromohydrins. Epoxidation (peracids, and via bromohydrin), hydroboration (basic mechanism) and dihydroxylation (e.g. with OsO4, and via epoxide hydrolysis) of alkenes. Nucleophilic addition to the carbonyl group: Introduction - structure and bonding, polarisation, oxidation levels, leaving group ability and the influence of attached atoms on reactivity. Principle reactions with nucleophiles, electrophiles and bases and loci of reactivity. Addition of HCN, hydride, organometallic reagents Nucleophilic substitution at the carbonyl group: Acetal and imine formation, the Wittig reaction (basic mechanism). Nucleophilic substitution at the carbonyl group in carboxylic acid derivatives: Addition-elimination reactions, the tetrahedral intermediate. Mechanism of formation of esters from acids and alcohols – role of acid catalysis. Preparation using acid chlorides. Hydrolysis of esters (acid and base-catalysed – including simple mechanisms), Reactions with nucleophiles: (i) with simple Grignards; (ii) with amines; (iii) reduction by LiAlH4., Formation of amides from acid chlorides and esters. Hydrolysis (low reactivity). Nitriles: Formation from alkyl halides. Hydrolysis to carboxylic acids. Reactions with nucleophiles: (i) reduction by hydride reducing agents; (ii) reactions with simple Grignard reagents to give ketones. An introduction to enolate chemistry: Including ?-alkylation of aldehydes, ketones and acid derivatives Completion of four practical experiments and associated reports covering a range of topics and skills in organic chemistry including the application of a variety of advanced techniques and methodologies (including spectroscopy) to the synthesis and analysis of molecules and materials; the ability to analyse experimental data to provide an explanation for the observed experimental outcomes; understanding the importance of experimental safety and time management

Learning and Teaching

Teaching and learning methods

Lectures, tutorials with group working and tutor support Practical chemistry: Prelaboratory e-learning; pre-lab skills lectures/ Seminars; practical sessions, supporting demonstrations, group and one-to-one tuition

TypeHours
Lecture24
Preparation for scheduled sessions48
Follow-up work24
Practical24
Wider reading or practice14
Revision10
Tutorial6
Total study time150

Resources & Reading list

Andrew Burrows, John Holman, Andrew Parsons, Gwen Pilling, and Gareth Price (2009). Chemistry3: Introducing inorganic, organic, and physical chemistry. 

D. Williams, I. Flemming (2008). Spectroscopic Methods in Organic Chemistry. 

J Clayden, N Greeves and S Warren (2012). Organic Chemistry. 

James Keeler and Peter Wothers (2008). Chemical Stucture and Reactivity. 

M. Hesse, H. Meier, B. Zeeh (2008). Spectroscopic Methods in Organic Chemistry. 

Assessment

Assessment Strategy

The practical and theory (examination and tutorial) components must be passed separately at the module pass mark for the student’s programme, i.e. 40% if core, 25% if compulsory or optional (if compensation is allowed). All absences from practical sessions must be validated. Unexcused absences will result in failure of the module.

Formative

Tutorial

Summative

MethodPercentage contribution
Assessed Tutorials 10%
Examination  (2 hours) 65%
Practical write-ups 25%

Referral

MethodPercentage contribution
Examination  (2 hours) 75%
Practical write-ups 25%

Repeat Information

Repeat type: Internal & External

Linked modules

Repeat year externally: allowed if practical component passed. The practical marks are retained, the theory assessment is exam only. Repeat year internally: note that practical may be reassessed by resubmission of reports or repeated.

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