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 HIGHER ORGANIC CHEMISTRY
Code CHEM058
Coordinator Dr JW Gaynor
Chemistry
J.W.Gaynor@liverpool.ac.uk
Year CATS Level Semester CATS Value
Session 2015-16 Level 5 FHEQ Second Semester 7.5

Aims

The aim of this module is to introduce students to the fundamental principles that underpin modern organic chemistry.  Particular emphasis will be placed on relating each topic studied to examples of pharmacological significance.


Learning Outcomes

Learning Outcomes:

By the end of this course students will have acquired an understanding of

·        Various aspects of stereochemistry

·        Basic carbonyl chemistry

·        Acetals and sugar chemistry

·        Peptide synthesis, protecting groups and combinatorial chemistry

·        Aromaticity and the chemistry of five and six membered heterocycles

·        Chemistry of DNA and antivirals

·        Chemical bonding at enzymes and receptors

and will be able to use these concepts and principles to solve simple problems in organic chemistry.

Syllabus
1  1

Introduction to Organic Reaction Mechanisms : Text (M. Hornbyand J. Peach; "Foundations

of Organic Chemistry," Oxford Chemistry Primers, Oxford Science Publications, 1993) 

  1. Organic Reagents: Nucleophiles, Electrophiles, Radicals.
  2. Resonance Structures
  3. Curly Arrows
  4. Electronegativity
  5. Reaction Mechanisms: Substitution (SN1, SN2), Elimination (E1, E2)
2

 Static Stereochemistry (CGW&W chapt. 16) 

  1. Stereoisomers
  2. Chirality: enantiomers, chiral radiation (optical activity) ,chiral reagents (enzymes), asymmetric centres
  3. Absolute configuration: R,S system, D,L, Fischer
  4. Diastereoisomers
  5. Resolution: chiral reagent, conversion intocovalent/non-covalent diastereoisomers, chiral         chromatography
  6. Racemisation and epimerisation
3

Dynamic Stereochemistry (CGW&W chapt. 18)  

  1. Conformation and configuration
  2.  Barriers to rotation around single bonds
  3.  Linear alkanes: ethane, propane, butane
  4. Substituted alkanes. Conformational Analysis
  5. Cyclic alkanes: cyclo-propane/butane/pentane/hexane,substituted cyclohexanes
4

Carbonyl Chemistry 1 ; Text : "Core Carbonyl Chemistry," J. Jones, Oxf ord Chemistry Primers, OUP, 1997, ISBN: 0198559593 See also CG&W, Chapter 6, Page 136)

  1. The Carbonyl Group
  2. Types of Carbonyls
  3. Preparation of Carbonyls
  4. Reactivity of the Carbonyl Group: Non Reversible Addition Reactions
  5. Reversible Additions to the Carbonyl Group
5

Acetals  and Sugar Chemistry (Clayden, Greeves,Warren and Wothers) (CG&W), Chapters 6 and 49) 

  1. Reversible Addition to the Carbonyl Group
  2. Acetal Fomation
  3. Intramolecular Acetal Formation
  4. Sugars and Glycosides
  5. Phase I and Phase II Drug Metabolism: The Chemistry of Glucuronidation
6

Carbonyl Chemistry  2 : Aldol Condensation  (CG&W, Chapter  27) 

  1. Base cataysed Aldol
  2. Acid Catalysed Aldol
  3. Retro-aldol  in Biosynthetic Pathways
7

Amino Acid and Peptide Synthesis :  (CG&W, Chapter  25) 

  1. Amides
  2. Amide Structure
  3. Peptides and Protein Structure
  4. Protecting Groups
  5. Selective Synthesis of a Dipeptide.
8

Aromaticity and Benzene Chemistry:  (CG&W, Chapters7 and 22) 

  1. Aromaticity and the Hückel (4n +2π) Rule
  2. Bonding in Benzene
  3. Electrop hilic Reactions of Benzene
  4. Effects of Substituents on electrophilic Substitution
  5. Nucleophilic Aromatic Substitution: Synthesis of Antibacterial Sulfones
9

Heterocyclic Chemistry 1:Pyridine Chemistry: (CG&W, Chapter 43) 

  1. Pyridines
  2. Naturally Occurring Pyridines and Important Pharmaceuticals
  3. Bonding in Pyridine: Protonation of Pyridine and Water Solubility
  4. Synthesis of Pyridines
  5. Electrophilic Substitution
  6. Nucleophilic Addition
  7. Addition Elimination: Synthesis of Important  Pyridine  Containing Chemotherapeutic Drugs
10

Heterocyclic Chemistry   2:Pyrrole Chemistry : (CG&W, Chapter 43) 

  1. Important  Pyrroles and Drugs Containing the Pyrrole Function
  2. Bonding in Pyrrole
  3. Electrophilic Substitution on Pyrrole
  4. Deprotonation of Pyrrole
  5. The Synthesis of Pyrroles
11

Heterocyclic Chemistry   3:Pyrimidines and Purines : (CG&W, Chapter 43) 

  1. Nucleic Acids
  2. Structure of DNA
  3. Modified Nucleosides as Drugs
  4. The Synthesis of AZT
12

Chemical Bonding at Receptors and Enzymes (Nogrady, T., Medicinal chemistry - A biochemical approach , 2nd Edn Oxford U.P.,1990.) 

  1. Hydrophobic Interactions
  2. Hydrogen Bonding
  3. Charge Transfer
  4. Dipole Interactions
  5. Ionic Bonds
  6. Covalent Bonds
13

Revision


Teaching and Learning Strategies

Lecture -

Other -


Teaching Schedule
  Lectures Seminars Tutorials Lab Practicals Fieldwork Placement Other TOTAL
Study Hours 16

         4

 20
Timetable (if known)              
Private Study 55
TOTAL HOURS 75

Assessment
EXAM Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Written Exam  1.5 hours  First  90  August    Assessment 2 Notes (applying to all assessments) Two Workshops This work is not marked annonymouslyWritten Examination  
CONTINUOUS Duration Timing
(Semester)		 % of
final
mark		 Resit/resubmission
opportunity		 Penalty for late
submission		 Notes
Coursework  2 hours  Friday 10-12, weeks 9 and 11.  10  No  Penalty for late submission applies - see Departmental handbook for details.  Assessment 1 

Recommended Texts
Reading lists are managed at readinglists.liverpool.ac.uk. Click here to access the reading lists for this module.
Explanation of Reading List: