Structure, Reactivity and Mechanism in Organic and Bioorganic Chemistry

Overview

Dr Paul Dingwall
p.dingwall@qub.ac.uk
Carbonyl Chemistry and Acidity (6 Lectures, Seminar)

Module Coordinator, Laboratory Coordinator
Dr. Chris Murgnaghan
c.murgnaghan@qub.ac.uk
Infrared, NMR and Mass Spectroscopy (6 Lectures, Seminar);
Aromaticity and Aromatic Chemistry (6 Lectures, Seminar)

Dr Mark McLaughlin
m.mclaughlin@qub.ac.uk
Oxidation And Reduction REDOX Processes (6 Lectures, Seminar)

Dr Stephen Cochrane
s.cochrane@qub.ac.uk
Organic Chemistry Workshops (3 x 2h Workshops)
SEMESTER 2

INFRARED, NMR AND MASS SPECTROSCOPY (Dr C. Murgnaghan):
• The electromagnetic spectrum. Energy absorption.
• IR Spectroscopy
• Hooke's Law approximation, stretching and bending vibration modes.
• R spectrometers.
• Characterisation by IR spectroscopy - group frequencies, finger print region. * Specific group frequencies - C-H stretch, (bend), C=C and C=C stretch, O-H stretch, N-H stretch, C=O stretch (and factors affecting it), C=N stretch, o-, m-, p-bend in mono- and disubstituted benzene derivatives.
• Uses of IR spectroscopy.* A Brief Introduction to 1H NMR Spectroscopy* The Nuclear Magnetic Resonance (NMR) Spectrometer.
• Examples of 1H NMR spectra of various small organic molecules.
• The concepts chemical shift variation; shielding and deshielding effects. Spin-Spin Splitting and the (n+1) rule.
• Applications of spectroscopic methods in structure identification.

AROMATICITY AND AROMATIC CHEMISTRY(Dr C. Murgnaghan):
• The Huckel Rule of Aromaticity
• The bonding in benzene: concepts of resonance, delocalisation and aromatic stabilisation. *
• Nomenclature of substituted aromatics.
• Electrophilic Aromatic Substitution Reactions: mechanisms and prominent (name) reactions: nitration, halogenation, acylation, and alkylation.
• Directing Effects in Electrophilic Aromatic Substitution Reactions.
• Aromatic amines and diazonium salts: preparation and reactions of.
• Electrophilic substitution of heteroaromatic compounds.
• Diazotisation of aniline, Nucleophilic substitution of diazonium species. Preeparation of phenols.
• Synthesis and strategies in preparation of polysubstituted benzenes.

CARBONYL CHEMISTRY AND ACIDITY (Dr P. Dingwall)
• Develop an understanding of the pKa and pKaH scales.
• Appreciate how the pKaH scale can be used to determine nucleophile strength and leaving group ability.
• Reason through the factors that affect the stability of a conjugate base and appreciate how to use this knowledge to predict approximate pKa values and positions of equilibrium.* Understand factors that govern nucleophilic addition to the carbonyl group.
• Understand the differences between acid and base catalysed mechanisms.
• Understand factors that govern nucleophilic substitution at the carbonyl group.
• Be able to predict whether a nucleophilic substitution to a carbonyl group is likely to proceed.
• Appreciate the differences in reactivity of α,β-unsaturated carbonyl compounds
• Understand the factors that control the regioselectivity of 1,2- vs 1,4-addition in such α,β-unsaturated systems
• Understand the impact of kinetic and thermodynamic control in organic reactions.

OXIDATION AND REDUCTION REDOX PROCESSES (Dr Mark McLaughlin):
• Definition of REDOX processes.
• Functional group interconversions based on REDOX processes.
• Classes of oxidants including oxygen, ozone, N-oxides, peroxides, peroxyacids, transition metal and p-block elements in high oxidation states.
• Classes of reductants including hydrogen, hydrides of boron and aluminium, and electropositive elements such as sodium and magnesium.

ORGANIC CHEMISTRY WORKSHOPS (Dr Stephen Cochrane):
• Practice and application of all the chemistry covered in this course

Learning Objectives

On completion of this module the students will have gained a theoretical and practical understanding of basic Organic Chemistry. They will be able to relate organic chemistry to pharmaceutical and biological subjects.

Skills

Learners are expected to demonstrate the following on completion of the module:
•You will learn how to take good notes from lectures.
•You will begin to understand the principles of mechanistic organic chemistry and ‘curly-arrow’ pushing, and learn the basic language that we speak in the organic chemistry world.
•You will learn how to preform functional group interconversions build simple acyclic molecules from simple, readily-available organic chemical starting materials and basic chemical feedstocks.
•You will become familiar with how to perform organic chemical reactions in the laboratory.

Assessment

Assessment

Element type: Element weight (%):
Examination (Session 2) 60
Practicals 20
Online quizzes 20

Course Requirements:
• Laboratory Course attendance and submission of post-labs at 80% or higher;
• All examinations must be passed at 40% or higher.