Module Code - Title:
CH4104
-
ORGANIC CHEMISTRY 3
Year Last Offered:
2025/6
Hours Per Week:
Grading Type:
N
Prerequisite Modules:
CH4103
CH4102
Rationale and Purpose of the Module:
To build on and extend the foundation chemistry covered in CH4102 and CH4103; to highlight heterocyclic chemistry as a key part of this extension; to develop the associated chemistry, reactions, biological importance of various heterocyclic compounds; to give the student a basic working knowledge and comprehension of the biomolecules û aminoacids, peptides and carbohydrates; to carry out practical work to support and reinforce some of the theoretical aspects encountered.
Syllabus:
Protein Chemistry:
Amino Acids: structure; synthesis and resolution; stereochemistry; isoelectric point; preparation from a-haloaminoacids; Gabriel Synthesis; Strecker Synthesis.
Peptides: Sequence determination: N and C terminal analysis; strategy for synthesis, use of protecting groups and activating agents, solid state synthesis using Merrifield resin.
Carbohydrate Chemistry:
Monosaacharides: aldoses and ketoses; structure and stereochemistry; hemiacetal and hemiketal formation; Fischer Projections, Haworth representation, chair conformation; oxidation and reduction reactions. Disaacharides: Glycosides (sugars as acetals and ketals); structure; reducing and non-reducing disaacharides. Polysaacharides: structure and occurrence.
Heterocyclic Chemistry:
5-Membered ring aromatic heterocycles: structure, aromaticity; electrophilic aromatic substitution reactions- reactivity and orientation; 5-membered ring non-aromatic heterocycles: structure and synthesis. Basicity of aromatic /non-aromatic N-heterocycles.
6-membered ring aromatic and non-aromatic N-heterocycles: Structure, properties; electrophilic and nucleophilic aromatic substitution reactions of pyridine; reactivity and orientation; basicity. Azoles and Fused 5-membered ring aromatic heterocyles; Structure, basicity (where relevant); Azines. Nucleic acids. Occurrence/application of all types of heterocycles encountered above. Current trends.
Learning Outcomes:
Cognitive (Knowledge, Understanding, Application, Analysis, Evaluation, Synthesis)
On successful completion of this Module the student should be able to
1. Plot and examine the ionization profile of a typical aminoacid as a function of pH.
2. Outline in detail the synthesis of simple aminoacids.
3. Identify the problems associated with the chemical synthesis of peptides and show the standard methodology used for circumventing these problems.
4. Draw the appropriate structures for simple mono-, di- and polysaacharides.
5. Indicate some of the typical reactions these undergo.
6. Identify and draw the various classes of heterocyclic molecules.
7. Relate the structure of the heterocycles to their chemical behaviour.
8. Indicate examples of the biological importance/other of some of these heterocycles.
Affective (Attitudes and Values)
By the end of the Module the student should
1. Demonstrate an appreciation of the importance of having a broad and integrated knowledge of the many aspects of foundational chemistry, along with its application to biomolecules.
Psychomotor (Physical Skills)
On successful completion of this Module the student should
1. Present a record in the form of a brief organized report of oneÆs own experimental work carried out safely and independently.
How the Module will be Taught and what will be the Learning Experiences of the Students:
This module will be taught over a 12 week period through a formal interactive lecturing mode (2 x 1 hour lectures; 1 hour tutorial per week); students will carry out relevant laboratory work throughout the semester (5 x 3 hour sessions).
The Module will be assessed by the following means:
End-of-semester written exam (75%); laboratory work (25%)-whereby the studentÆs written record of each experiment in the form of a report will be assessed.
Research Findings Incorporated in to the Syllabus (If Relevant):
N/A
Prime Texts:
Wade L.G. Jr (2006)
Organic Chemistry
, Pearson/Prentice Hall
Ege Seyhan (2004)
Organic Chemistry-Structure and Reactivity
, Haughton Mifflin Co.
Fox Marye Ann and Whitesell J.K. (2004)
Organic Chemistry
, Jones and Bartlett
Peter K., Vollhardt C. and Schore N.E. (2002)
Organic Chemistry-Structure and Function
, W.H. Freeman and Co.
Bruice Paula Yurkanis (2007)
Organic Chemistry
, Pearson Education
Loudon G.M. (2002)
Organic Chemistry
, Oxford Press
Other Relevant Texts:
Oulette R.J. (1998)
Organic Chemistry-A Brief Introduction
, Prentice Hall
Johnson William A. (1999)
Invitation to Organic Chemistry
, Jones and Bartlett
Programme(s) in which this Module is Offered:
Semester(s) Module is Offered:
Module Leader:
matteo.lusi@ul.ie