Organic Chemistry Level 1

Overview

SEMESTER 1

INTRODUCTION TO ORGANIC STRUCTURE (Dr H. Crory):
 Structural formula to represent organic compounds, identify isomers and convert structural formula to molecular formula.
 Structure-property relationships of common organic functional groups, giving rise to stability, reactivity and solubility.
 Conformation and stereoisomerism including R&S, E&Z, and D&L notation.

INTRODUCTION TO ORGANIC REACTIVITY (Dr P. Dingwall):
 Reading an organic reaction, recognition of nucleophiles and electrophiles
 Role of mechanism in organic chemistry and the use of curly arrows
 Nucelophilic substitution at saturated carbon
 Elimination reactions
 Alkene addition reactions

ORGANIC CHEMISTRY SEMESTER 1 WORKSHOPS (Dr H. Crory and Dr P. Dingwall):
 Organic structure
 Organic reactivity


SEMESTER 2

OXIDATION AND REDUCTION REDOX PROCESSES (Dr M. 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.

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.



AROMATICITY AND AROMATIC CHEMISTRY (Dr C. Murnaghan):
 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.

INFRARED, NMR AND MASS SPECTROSCOPY (Dr C. Murnaghan):
 The electromagnetic spectrum. Energy absorption.
 IR Spectroscopy
 Hooke's Law approximation, stretching and bending vibration modes.
 IR 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.

ORGANIC CHEMISTRY SEMESTER 1 WORKSHOPS (Dr P. Knipe):
 Practice and application of all the chemistry covered in this course
 SN1, SN2, E1, and E2 reactions
 Carbonyl chemistry
 REDOX chemistry

Learning Objectives

On successful completion of this module the student will:

On successful completion of this module students will:
 Have a good working knowledge of the fundamental reactions and reagents of synthetic organic chemistry and of the chemistry of important, commonly-encountered, organic functional groups.
 Be capable of drawing basic organic reaction mechanisms and have a good awareness of key stereochemical principles and factors determining organic molecule reactivity.
 Begin to develop an understanding of the pKa scale and its uses for understanding reactivity
 Understand and rationalise reactivity of nucleophilic addition and substitution at the carbonyl group
 Be able to use IR, UV/VIS, Mass and NMR spectroscopies to help determine the structures of organic molecules.
 Master the rudiments of practical experimental organic chemistry.

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 do organic chemical reactions in the laboratory.

Assessment