Form 20
Module Title
Module
Co-ordinator
Version 3.0 (2007/2008)
Heriot-Watt University - Module Descriptor Template (RAY)
Organic Structural Identification, Stereochemistry
& Reaction Mechanisms
Dr J.H. Cameron
School
Engineering and Physical Sciences
SCQF
Level
8
Module
Code
1. Pre-requisites
Minimum D grade in Stage 1 Chemistry modules, or the equivalent
2. Linked Modules
(specify if synoptic)
3. Excluded Modules
Synthesis in Organic Chemistry (synoptic)
4. Replacement Module
Code:
6. Degrees for which this
is a core module
7. Aims
Date Of Replacement:
All Chemistry degrees
5.
B18OA
Availability as an
Elective
Semester
Yes

1
On or OffCampus
Credits
On
15
No
The module aims to:
 provide an introductory course on the principles of ir, uv, mass and nmr spectroscopy, as they relate to the determination of chemical structures of
organic compounds
 conduct exercises on structure determination of simple organic compounds through use of the above methods
 describe and apply conformational analysis to a range of acyclic and cyclic molecules
 describe and apply configurational analysis to a range of acyclic and cyclic molecules
 demonstrate how stereochemical outcomes of organic reactions are influenced by structural and mechanistic considerations
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Form 20
Module Title
Module
Co-ordinator
Version 3.0 (2007/2008)
Heriot-Watt University - Module Descriptor Template (RAY)
Organic Structural Identification, Stereochemistry
& Reaction Mechanisms
Dr J.H. Cameron
School
Engineering and Physical Sciences
SCQF
Level
8
Module
Code
B18OA
Semester
1
On or OffCampus
Credits
On
15
8. Syllabus


Molecular formulae – derivation of molecular formulae through use of elemental analysis and mass spectroscopy; use of ‘double bond equivalents’
Mass spectrometry – molecular ion, fragmentation, molecular ion peak patterns (isotopes), electron-impact and chemical ionisation mass spectrometry, highresolution mass spectra
 Infrared spectroscopy – use of infrared spectroscopy for identifying functional groups
 Ultraviolet-visible spectroscopy – basis of UV spectroscopy and its use for identifying conjugated systems, in particular conjugated carbonyl and aromatic
compounds
 Fundamental aspects of 1H and 13C nmr spectroscopy – chemical shifts, multiplicities, integrals, deduction of molecular structure; broadband decoupled 13C
NMR, off-resonance decoupling, DEPT
 Solving molecular structures through combined use of the above methods
 Conformational Analysis – Conventions for representing organic structures; Conformations of Simple Acyclic Systems; Conformations of Monocyclic Systems;
Conformations of Polycyclic Aliphatic Systems; use of nmr techniques to determine structure (Karplus equation)
 Configuration Alkenes- Geometrical Isomerism;CIP sequence rules; E-, Z- nomenclature for alkenes; Compounds containing one Chiral Centre; R-, Snomenclature; Compounds with two or more Chiral Centres; Optical Activity of Organic Molecules without a Chiral Centre; Methods of Resolution of Racemic
Mixtures; Measurement of Chirality
 Mechanisms and Stereochemistry of Organic Reactions – Syn Additions to Alkenes; Anti Additions to Alkenes; E2 Elimination Reactions; E1 Elimination
Reactions; Addition Reactions at Carbonyl Groups of Aldehydes and Ketones; Stereochemistry of Substitution Reactions at Chiral Centres
 Ethers and Epoxides – Nomenclature and Structure Simple Acyclic and Cyclic Ethers; Synthesis of Simple Ethers; Cleavage of ethers with HI or HBr;
Nomenclature and Structure of Epoxides; Synthesis of Epoxides; Reactions of Epoxides; Crown ethers
9. Learning Outcomes (HWU Core Skills: Employability and Professional Career Readiness)
Subject Mastery
Understanding, Knowledge and Cognitive Skills
Scholarship, Enquiry and Research (Research-Informed Learning)
On completion of the module, the student will be able to
 demonstrate a broad knowledge of the principles of IR, UV and NMR spectroscopy, and mass spectrometry, in their application to
the determination of the chemical structures of organic molecules
 successfully practice using the above knowledge to solve the molecular structures of simple organic compounds
 undertake the critical analysis of spectroscopic problems
 apply spectroscopic methods to the solution of chemical problems
 Demonstrate a systematic approach to structural analysis of organic molecules
 Be aware of the quantification of conformational populations using thermodynamics and spectroscopy
 Show an enhanced awareness of how the structures of organic molecules can influence reaction outcome.
 Discuss the applications of structural analysis to organic synthesis with extensions to advanced concepts such as chiral induction
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Form 20
Module Title
Module
Co-ordinator
Version 3.0 (2007/2008)
Heriot-Watt University - Module Descriptor Template (RAY)
Organic Structural Identification, Stereochemistry
& Reaction Mechanisms
Dr J.H. Cameron
School
Engineering and Physical Sciences
SCQF
Level
8
Module
Code
B18OA
Semester
1
On or OffCampus
Credits
On
15
Personal Abilities
Industrial, Commercial & Professional Practice
Autonomy, Accountability & Working with Others Communication, Numeracy & ICT
Personal abilities are embedded in the module. The module provides the opportunity to :
 Use ICT skills with on-line materials, assessments (formative and summative) and web links to support the learning process
 develop oral communication abilities through small group tutorials
 use and evaluate spectroscopic data
 Use molecular models and molecular modeling packages to visualize and understand structure
 Practice the extensive use of problem solving approach to encourage consolidation and application of structural concepts
 Use a VLE and other on-line Web sites and resources to enhance the student learning experience and promote independent learning
 Participate in tutorial sessions designed to promote discussion of course-related topics with professional-level colleagues.
 Use an evaluate numerical and graphical data
 Demonstrate numerical, graphical and problem-solving skills in a range of areas
 Manage time effectively, work to deadlines and prioritise workloads
 Communicate complex ideas and information effectively to a group of peers
 Apply strategies for appropriate selection of relevant information from a body of knowledge
 Practise the use of standard methods in the solution of routine chemical problems within familiar contexts
 Exercise some initiative and independence in carrying out defined problem solving activities
 Critically use mathematical methods to analyse various chemical reactions variables
 Interpret, use and evaluate a wide range of data to solve problems of both a familiar and unfamiliar nature
 Evaluate numerical, graphical and spectroscopic data and apply them to the solution of chemical problems
 Manage resources in defined areas of activity
 Work with peers in small groups in the discussion of chemical problems
10. Assessment Methods
11. Re-assessment Methods
Method
Duration of Exam
Weighting (%)
Synoptic modules?
Method
Duration of Exam
(if applicable)
Synoptic Examination
Class test
Continuous Assessment
Laboratory Work
12. Date and Version
Date of Proposal
24 August, 2007
3h
2h
Date of Approval by
School Committee
(if applicable)
50%
15%
15%
20%
B18OB
Synoptic Examination (100%)
Date of
Implementation
15 September, 2008
3h
Version
Number
1.0
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