Organic Chemistry Level 1

Overview

STAFF

NAME CONTRIBUTION
Prof. Paul J. Stevenson
p.stevenson@qub.ac.uk
Introduction to Organic Chemistry and Functional Group Chemistry Part 1
(18 Lectures, Seminar); Oxidation And Reduction REDOX Processes (6 Lectures, Tutorial, Seminar)

Semester 1 CHM1101 Practical Class Coordinator
Dr. Kirill Tchabanenko
k.tchabanenko@qub.ac.uk
Infrared, NMR and Mass Spectroscopy (6 Lectures, Tutorial, Seminar); Aromaticity and Aromatic Chemistry (6 Lectures, Tutorial, Seminar)

Semester 2 CHM1101 Practical Class Coordinator and Module Cordinator
Dr Paul Dingwall
p.dingwall@qub.ac.uk
Carbonyl Chemistry and Acidity (6 Lectures, Tutorial, Seminar)
1 Revision Lecture, 1 Tutorial

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

Contents:
SEMESTER 1

INTRODUCTION TO ORGANIC CHEMISTRY (Prof. P. J. Stevenson):
 Structural formula to represent organic compounds, identify isomers and convert structural formula to molecular formula.
 Conformation, stereoisomerism sequence rule and diastereoisomerism.
 Role of mechanism in Organic Chemistry. Recognition of nucleophiles, electrophiles and bases
 Chemistry of common organic functional groups, Structure and prediction of chemistry and reactivity.
 Electrophilic addition to alkenes and alkynes.
 Electrophilic substitution of aromatic compounds.
 Chemistry of alcohols and conversion to alkyl halides
 SN1, SN2, E1, and E2 mechanisms.
 Chemistry of amines
 The chemistry of the carbonyl group. Nucleophilic addition, substitution by nucleophilic addition elimination.

SEMESTER 2

OXIDATION AND REDUCTION REDOX PROCESSES (Prof. P J Stevenson):
 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 K. Tchabanenko):
 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 K. Tchabanenko):

 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 WORKSHOPS (Dr Stephen Cochrane):

 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

summary of overall assessment weights (100%):
class tests 10%
examination 60%
laboratory work 15%
tutorial tests 15%

Course Requirements:
 Laboratory Course attendance and submission of reports, 80% or higher;
 All examinations and Class Tests must be passed at 40% or higher.
 Tutorial attendance and submission of the mandatory Tutorial Course work.

Detail of assessments:

1 x 1 h Class Test worth 10% of the overall Module Mark on the Semester 1 CHM1101 Organic Chemistry lecture material covered by Prof Stevenson.

N.B. This 1st CHM1101 Class Test will be staged jointly and concurrently with the 1 h CHM1011 Class Test set by Dr Andrew Marr.

It will be conducted under proper, invigilated, Exam conditions in Week 13.

In addition to this 1st CHM1101 Class Test, there will be:

1 x 1 h Invigilated 2nd Class Test worth 5% of the overall Module Mark on the Organic Chemistry Spectroscopy Lecture material covered by Dr Tchabanenko (Week 13, 1st Semester).


Satisfactory progression into the Semester 2 CHM1101 lecture course will be contingent on students satisfactorily PASSING both CHM1101 Semester 1 Class Tests at a mark of 40% or higher.

Failure to pass either of these Class Tests will prevent students from progressing into the CHM1101 Lecture course in Semester 2, and it will lead to failure of the entire CHM1101 module, which will require students to repeat the entire Yr 1 course, in the next academic year.

1 x 3 h Examination (May, 3rd Semester)

The May Exam (Semester 3) will examine exclusively the Semester 2 lecture material of Prof Hale, Dr Dingwall and Dr Tchabanenko.

It will consist of a single 3 h duration Exam and it will be held in a University designated Examination Hall under normal tightly invigilated examination conditions (circumstances permitting).

The 3 h May Examination will be worth 60% of the final total module mark and it will be split into 3 compulsory sections, which all must be answered:

Section A will examine the Prof Hale lecture course material and will require candidates to answer 3 out of 4 questions.

Section B will examine Dr Dingwall’s lecture course material and will require candidates to answer 1 compulsory question.

Section C will examine Dr Tchabanenko’s Semester 2 lecture course material on Aromatic Chemistry and it will require candidates to answer 1 compulsory question.

Candidates will be given 10 min Examination paper reading time, before the Examination will formally begin.

Laboratory Class Attendance, Written Lab Reports and Samples Submitted
(Semesters 1 and 2)

Tutorial Tests (Semesters 1 and 2)



.