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CHEM1031 Fundamentals of Organic Chemistry I

Module Overview

Aims and Objectives

Module Aims

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.). Lecture component: The aim of this organic chemistry course is to introduce students to many of the key concepts of structure and reactivity in organic chemistry: Structure – of molecules: functional groups, isomerism including stereochemistry and optical activity, nomenclature, introduction to infrared spectroscopy (functional groups); bonding (electronic structure, orbitals, hybridisation and shape); conformational analysis of linear and cyclic molecules. Reactivity – drawing and predicting resonance structures and reaction mechanisms by using curly arrows; understanding electron-rich and electron-deficient sites and species; acidity (alcohols, phenols, carboxylic acids, sulfonic acids, as well as halogen, nitrogen and carbon acids); basicity (conjugate bases of all classes of acids studied, and including such common bases as BuLi, LDA, NaH, hydroxide and alkoxides, amines); connections between electronic effects and acidity/basicity; aromaticity and introduction of the reactivity of aromatic compounds compared to alkenes; nucleophilic substitution at sp³ carbon (SN1 and SN2 mechanisms). 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 a series of four experiments, of which the titles below are examples: • Recrystallisation • Monitoring reactions • Influencing equilibria-carotene 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 and name a wide range of functional groups and interpret their IR spectra
  • Explain the connections between electronic effects and acidity/basicity
  • Explain the concept of aromaticity and identify both aromatic and non-aromatic molecules
  • Describe nucleophilic substitution reactions by both the SN1 and SN2 mechanisms
  • Explain the factors that influence SN1 and SN2 reaction rates, including the roles of steric effects, orbital effects and electronic effects.
  • Evaluate the risks associated with an experiment and understand how to mitigate those risks.
  • Set up glassware and apparatus to conduct experiments in Organic Chemistry.
  • Interpret data from a range of physical techniques to characterise Organic compounds.
  • Present the results of a practical investigation in a concise manner.
  • Draw representations of the chemical structure of organic molecules using a concise notation.
  • Understand and use sawhorse and Newman projections, 3D structures of organic molecules including cyclic structures
  • Name a wide range of organic molecules, including stereochemistry
  • Describe the structure (including electronic configuration) of organic molecules in terms of orbitals, hybridisation and conformation, including stereoisomerism
  • Understand the relative stability of conformations of linear and cyclic organic molecules.
  • Identify electron-rich and electron-poor sites within molecules, by using the concepts of electronegativity, inductive effects and mesomeric (resonance) effects
  • Apply the curly arrow notation to describe both resonance and reaction mechanisms
  • Predict the relative acidity and basicity of organic molecules, and describe these properties with the concepts of pKa and pKaH

Syllabus

Structure – of molecules: functional groups, isomerism including optical activity, nomenclature, introduction to infrared spectroscopy (functional groups); bonding (orbitals, hybridisation and shape of organic species); conformational analysis. Reactivity – curly arrows, electron-rich and electron-deficient species, acidity (alcohols, phenols, carboxylic acids, and C—H acids); basicity (BuLi, LDA, hydroxide and alkoxides, amines); resonance; aromaticity and introduction of the reactivity of aromatic compounds compared to alkenes; nucleophilic substitution at sp³ carbon (SN1 and SN2 mechanisms). 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 fundamental 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. Practical hours includes pre-laboratory e-learning.

TypeHours
Wider reading or practice15
Preparation for scheduled sessions48
Lecture24
Tutorial5
Revision10
Practical24
Follow-up work24
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. 

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

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

Assessment

Assessment Strategy

The practical and examination 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

In-class Test

Summative

MethodPercentage contribution
Examination  (1.5 hours) 75%
Practical write-ups 25%

Referral

MethodPercentage contribution
Examination  (1.5 hours) 75%
Practical write-ups 25%
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