Organic Chemistry 1

Overview

INTRODUCTION TO ORGANIC REACTIVITY
*Reading an organic reaction, recognition of nucleophiles and electrophiles
*Role of mechanism in organic chemistry and the use of curly arrows
*Nucleophilic substitution at saturated carbon
*Elimination reactions
*Alkene addition reaction

CARBONYL CHEMISTRY AND ACIDITY
*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
*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.

AROMATICITY AND AROMATIC CHEMISTRY
*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. Preparation of phenols.
*Synthesis and strategies in preparation of polysubstituted benzenes.

Learning Objectives

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 the fundamentals of carbonyl chemistry, particularly addition and substitution reactions
*Understand what is required for an oxidation or reduction reaction to occur
*Develop an understanding of the chemistry surrounding aromatic molecules

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 understand the different mechanisms behind nucleophilic substitution, elimination, and alkene addition, and be able to reason products from given starting materials by suggesting a mechanism through which the transformation occurs
*You will be able to estimate pKa values for protons in different environments
*You will be able to predict whether a given carbonyl substitution reaction will be likely to proceed
*You will determine the best reagents and conditions to choose to conduct an oxidation or reduction reaction of a given starting material
*You will be able to reason through inductive and mesomeric effects of differing functional groups on an aromatic ring and their relative abilities to direct electrophilic aromatic substitution reactions to predict the products of a given reaction

Assessment

Assessment Profile
Element type Element weight (%)
1. Examination (Spring) 90
2. Tutorials 10

Tutorial attendance and submission 80%.
All examinations must be passed at 40% or higher.