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The University of Southampton

CHEM1032 Fundamentals of Organic Chemistry II

Module Overview

Aims and Objectives

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.


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 α-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

Preparation for scheduled sessions48
Wider reading or practice14
Follow-up work24
Total study time150

Resources & Reading list

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

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. 

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

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


Assessment Strategy

All absences from practical sessions must be validated. Unexcused absences will result in failure of the module. 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.




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


MethodPercentage contribution
Examination  (2 hours) 100%
Lab proficiency 

Repeat Information

Repeat type: Internal & External

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