Module Details

The information contained in this module specification was correct at the time of publication but may be subject to change, either during the session because of unforeseen circumstances, or following review of the module at the end of the session. Queries about the module should be directed to the member of staff with responsibility for the module.
Title CHEM130 Introductory Organic Chemistry
Code CHEM130
Coordinator Professor N Greeves
Chemistry
Ngreeves@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2021-22 Level 4 FHEQ Whole Session 30

Pre-requisites before taking this module (or general academic requirements):

 

Aims

The aim of this module is to ensure that students are aware of fundamental principles of organic chemistry, including nomenclature, structure and bonding, and the basic principles of static and dynamic stereochemistry. The major reactions associated with the common functional groups will be covered with emphasis on reaction mechanisms. In addition, this module will provide an introduction to the basic techniques associated with practical synthetic chemistry.


Learning Outcomes

(LO1) By the end of this module students will know:
* Structures and shapes of major classes of organic compounds;
* Principles of bonding in major classes of organic compounds;
* Basic principles of stereochemistry;
* Important reactions of a range of functional groups;
* An understanding of the major classes of reaction mechanisms;
* The basic techniques of synthetic chemistry (isolation, purification, identification, and design and work-up of reactions)
and they will have experience of characterisation using spectroscopic techniques and chemical methods.

(S1) Problem solving skills

(S2) Organisational skills


Teaching and Learning Strategies

The theory part of this module will be delivered asynchronously in short lecture recordings throughout the year. The material presented is supported by 20 1.5 hour workshops. The practical aspects will be delivered through 4-4.5 days of laboratory time plus additional online activities linked to laboratory preparation and/or virtual experiments, a lab related workshop and an introductory lecture.


Syllabus

 

1
Organic structures
• Why we use these particular diagrams
• How organic chemists name molecules in writing and in speech
• What is the skeleton of an organic molecule
• What is a functional group
• Some abbreviations used by all organic chemists
• Drawing organic molecules realistically in an easily understood style
Structure of molecules ( to include simple sulfur and phosphorus compounds )
• How we know that electrons have different energies
• How electrons fit into atomic orbitals
• How atomic orbitals combine to make molecular orbitals
• Why organic molecules have linear, planar, or tetrahedral structures
• Connection between shape and electronic structure
• A true system of molecular orbital energies for simple molecules
• Why such rigour is not possible for typ ical organic molecule
• Predicting the locations of lone pairs and empty orbitals
• Interaction between theory and experiment
2
Organic reactions
• Why molecules generally don't react with each other!
• Why sometimes molecules do react with each other
• In chemical reactions electrons move from full to empty orbitals
• Molecular shape and structure determine reactivity
• Representing the movement of electrons in reactions by curly arrows
Nucleophilic addition to the carbonyl group
• How and why the C=O group reacts with nucleophiles
• Explaining the reactivity of the C=O group using molecular orbitals and curly arrows
• What sorts of molecules can be made by reactions of C=O groups
• How acid or base catalysts improve the reactivity of the C=O group
Declocalization and conjugation
&# x2022; Interaction between orbitals over many bonds
• Stabilization by the sharing of electrons over molecules
• Where colour comes from
• Molecular shape and structure determine reactivity
• Representing one aspect of structure by curly arrows
• Structure of aromatic compounds
Acidity, basicity, and pKa
• Why some molecules are acidic and others basic
• Why some acids are strong and others weak
• Why some bases are strong and others weak
• Estimating acidity and basicity using pH and pKa
• Structure and equilibria in proton transfer reactions
• Which protons in more complex molecules are more acidic
• Which lone pairs in more complex molecules are more basis
Using organometallic reagents to make C-C bonds
• Organometallics: nucleophilic and often strongly basic
• Making organometallics from halocompounds
• Making organometallics by deprotonating carbon atoms
• Using organometallics to make new C-C bonds from C=O groups
Nucleophilic substitution at the carbonyl (C=O) group
• Nucleophilic attack followed by loss of leaving group
• What makes a good nucleophile
• What makes a good leaving group
• This is always a tetrahedral intermediate
• How to make acid derivatives
• Reactivity of acid derivatives
• How to make ketones from acids
• How to reduce acids to alcohols
Nucleophilic substitution at C=O with loss of carbonyl oxygen
• Replacement of carbonyl oxygen
• Acetal formation
• Imine formation
• Stable and unstable imines
• Reductive amination
Stereochemistry
• Three -dimensional shape of molecules
• Molecules with mirror images
• Molecules with symmetry
• How to separate mirror-image molecules
• Diastereoisomers
• Shape and biological activity
• How to draw stereochemistry
Nucleophilic substitution at saturated carbon
• Nucleophilic attack on saturated carbon atoms, leading to substitution reactions
• How substitution at a saturated carbon atom differs from substitution at C=O
• Two mechanisms of nucleophilic substitution
• Intermediates and transition states in substitution reactions
• How substitution reactions affect stereochemistry
• What sort of nucleophiles can substitute, and what sort of leaving groups can be substituted
• The sorts of molecules that can be made by substitution
3
Conformational analysis
• ;If I could see a molecule, what would its three-dimensional shape (conformation) be?
• What effect does a molecule's shape have on its reactions?
• How single bonds are free to rotate, but spend most of their time in just two or three well-defined arrangements
• How rings of atoms are usually not planar, but "puckered"
• How "puckered" six-membered rings have the most well-defined arrangements of atoms
• How to use the known arrangements of the atoms in a six-membered ring to predict and explain their reactions
Elimination reactions
• Elimination reactions
• What factors favour elimination over substitution
• The two important mechanisms of elimination reactions
• The importance of conformation in elimination reactions
• How to use eliminations to make alkenes (and alkynes)
4
Electrophili c addition to alkenes
• Reactions of simple, unconjugated alkenes with electrophiles
• Converting C=C double bonds to other functional groups by electrophilic addition
• How to predict which end of an unsymmetrical alkene reacts with the electrophile
• Stereoselective and stereospecific reactions of alkenes
• How to make alkyl halides, epoxides, alcohols, and ethers through electrophilic addition
Electrophilic aromatic substitution
• Phenols as aromatic enols
• Benzene and alkenes compared
• Activation and deactivation
• Position of substitution
• Competition and co-operation
• Problems with some reactions
Formation and reactions of enols and enolates
• How carbonyl compounds exist in equilibrium with isomers called enols
• How acid or base promotes the formation of enols and their conjugate bases, enolates
• How enols and enolates have inherent mucleophilic reactivity
• How this reactivity can be exploited to allow the introduction of functional groups next to carbonyl groups
5
The laboratory course will cover the basic techniques of preparative chemistry which potentially includes but is not limited to-
• Recrystallisation from single and mixed solvents, filtration
• Determination of m.p.,m.m.p. and use of I.R. for identification
• Separation of acid/base/neutral compounds using either extraction etc., use of rotary evaporator
• TLC and GC for measure of purity and for following a reaction
• Use of NMR
• Distillation at atmospheric pressure
• Chemoselective reductions of 3-nitroacetophenone
• A simple oxidation reaction analysed by GC


Recommended Texts

Reading lists are managed at readinglists.liverpool.ac.uk. Click here to access the reading lists for this module.

Teaching Schedule

  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours       27

  51

30

108
Timetable (if known)              
Private Study 192
TOTAL HOURS 300

Assessment

EXAM Duration Timing
(Semester)
% of
final
mark
Resit/resubmission
opportunity
Penalty for late
submission
Notes
Online Class Tests (4 tests each 60 minutes) This is a compulsory component, i.e. it must be passed for passing the module. There is a resit opportunity in August  60 minutes    50       
CONTINUOUS Duration Timing
(Semester)
% of
final
mark
Resit/resubmission
opportunity
Penalty for late
submission
Notes
Laboratory work Standard UoL penalty applies for late submission. There is no re-sit opportunity for this component This is not an anonymous assessment. This is a compulsory component, i.e. it mu  27 hours    30       
Workshop Standard UoL penalty applies for late submission. There is no re-submission opportunity. This is not an anonymous assessment.  30 hours    20