University of the West of England

MODULE SPECIFICATION

Code: USSJ7L-20-2 Title: ORGANIC CHEMISTRY Version: 7

Level: 2 UWE credit rating: 20 ECTS credit rating: 10

Module type: STANDARD

Owning Faculty: Health and Life Sciences Field: Applied Sciences

Valid from: September 2003 Discontinued from:

Pre-requisites: USSJR9-20-1 Chemical Principles or USSJRA-20-1 Chemistry in Context

Co-requisites: None

Excluded combinations: None

Learning outcomes:

      • demonstrate a knowledge of useful, synthetic reactions and have an appreciation of the mechanisms of important organic reactions

      • assign the structure of simple organic compounds utilising a range of spectral techniques including 13C nmr spectroscopy and spectometry

      • utilise the disconnection approach in the design of synthetic routes to benzene derivatives

      • carry out techniques required for organic synthesis

Syllabus outline:

Aromaticity and aromatic substitution reactions:

    Molecular orbital structure and stability of benzene, the Huckel rule, its application to benzene and non-benzenoid aromatic structures such as the cyclopentadienyl anion and cycloheptatrienyl cation. Electrophilic aromatic substitution in monosubstituted benzene derivatives, orientation and reactivity effects of ring substituents towards electrophilic substitution. Nucleophilic aromatic substitution. Substitution of hydrogen in nitrobenzene, substitution of atoms other than hydrogen by unimolecular and bimolecular mechanisms and by an aryl mechanism.

Stereochemistry II:

    Application of the sequence rules to molecules with more than one chiral centre, stereoisomers with no chiral centres, allenes, spiro compounds, biphenyls. Axial and equatorial bonds in cyclohexane. Monosubstituted cyclohexanes, the hydrolysis of axial and equatorial ester groups. Conformation and reactivity.

Aldehydes and ketones:

    Preparation and relative reactivities of aldehydes and ketones. Oxidation and reduction. Nucleophilic addition to the carbonyl group. The Cannizzaro reaction, benzoin condensation, the Aldol condensation and related reactions. Halogenation of ketones and keto-enol tautomerism.

Synthetic intermediates:

    Carbanionoid reagents, their reactivity and use in the synthesis of ketones and carboxylic acids, including the preparation of some alicyclic derivatives. Review of the preparation of amines, reaction of amines with nitrous acid, including preparation of diazonium salts. Replacement and coupling reactions of diazonium salts. The Diels Alder reaction and its use in synthesis.

Heterocyclic Chemistry:

    Orbital structures of pyrrole, furan, thiophene and pyridine. The basicity of pyrrole and pyridine. Electrophilic substitution reactions of pyrrole and related compounds. Electrophilic and nucleophilic substitution reactions of pyridine.

Organic Spectroscopy II:

    Introduction to carbon-13 nmr spectroscopy, chemical shifts and spin-spin coupling. Comparison of proton and carbon-13 nmr spectroscopy. Applications in structure elucidation. Applications of mass spectrometry in organic chemistry, use of the molecular ion and discussion of some simple fragmentation patterns.

Retrosynthetic Analysis II:

    C-C and C-X bond forming reactions involving benzene derivatives. Design of synthesis of benzene derivatives.

Teaching and learning methods:

The module will be presented using lectures, practical work and tutorials. Directed student centred learning is an aspect of the course, particularly using software for enhancing the understanding of mass spectrometry and 13C NMR spectrometry.

Reading Strategy

All students will be encouraged to make full use of the print and electronic resources available to them through membership of the University. These include a range of electronic journals and a wide variety of resources available through web sites and information gateways. The University Library’s web pages provide access to subject relevant resources and services, and to the library catalogue. Many resources can be accessed remotely. Students will be presented with opportunities within the curriculum to develop their information retrieval and evaluation skills in order to identify such resources effectively.

This guidance will be available either in the module handbook, via the module information on UWEonline or through any other vehicle deemed appropriate by the module/programme leaders.

      • Williams D.H and Fleming I, Spectroscopic Methods in Organic Chemistry, McGraw Hill (1995).

      • McMurray J., Organic Chemistry, Brooks/Cole (2000).

      • Claydon J, Greeves N, Warren S, Wothers P, Organic Chemistry, Oxford University Press (2001).

Assessment

Weighting between components A and B (standard modules only) A: 60% B: 40%

ATTEMPT 1

First Assessment Opportunity

Component A Element weighting

EX3

Examination 3 HRS

1

     
     
 

 

Component B

Description of each element Element weighting

PR1

Practical write-ups based on laboratory work including questions related to theory and appropriate spectra

1

PR2

Practical write-ups based on laboratory work including questions on related theory. Problem solving assignment

1

     
     
     

Second Assessment Opportunity (further attendance at taught classes is not required)

Component A

Description of each element Element weighting

EX3 - REF

Examination (3 Hours)

1

     
     
 

 

Component B

Description of each element Element weighting

PR1 - REF

Students will be provided with data for laboratory experiments analagous to those carried out during the delivery of the module, including appropriate spectra. They will be expected to answer questions relating to information supplied and analyse the spectra.

1

PR2 - REF

Problem solving assignment

1

     
     
     

SECOND (OR SUBSEQUENT) ATTEMPT Attendance at taught classes is required.

Specification confirmed by …………………………………………………Date ……………………………

(Associate Dean/Programme Director)

Back to top