Fundamentals of Organic Chemistry II

Learning Outcomes

Learning Outcomes

Having successfully completed this module you will be able to:

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

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

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

Resources & Reading list

Textbooks

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

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

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

D. Williams, I. Flemming (2008). Spectroscopic Methods in Organic Chemistry. London: McGraw-Hill.

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

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.

Formative

This is how we’ll give you feedback as you are learning. It is not a formal test or exam.

Summative

This is how we’ll formally assess what you have learned in this module.

Referral

This is how we’ll assess you if you don’t meet the criteria to pass this module.

Repeat Information

Repeat type: Internal & External