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CHEM30210

Academic Year 2024/2025

Structure Determination and Aromatic Heterocyclic Chemistry (CHEM30210)

Subject:
Chemistry
College:
Science
School:
Chemistry
Level:
3 (Degree)
Credits:
5
Module Coordinator:
Professor Patrick Guiry
Trimester:
Autumn
Mode of Delivery:
Blended
Internship Module:
No
How will I be graded?
Letter grades

Curricular information is subject to change.

Mass Spectrometry - instrumentation; ion production by EI or CI; molecular ion; isotopes; N rule; fragmentation, rearrangement; characteristic processes of different organic classes; applications.Ultraviolet-Visible Spectroscopy - instrumentation; Types of electronic transitions; Conjugation; selected examples. Infrared Spectroscopy - types of vibration; Characteristic vibrations of different functional groups; emphasis on C=O group; applications. NMR Spectroscopy - introduction; CW vs FT NMR; 1H NMR; chemical shift; spin-spin coupling; integration; protons on heteroatoms; magnetic equivalence; AMX, ABX, and ABC spin systems; spin decoupling-1H-1H connectivity ; 13C NMR; decoupling; chemical shifts e.g. aromatic compounds; 2D NMR - 1H-1H connectivity (COSY); 1H-13C connectivity (APT, DEPT); nuclear Overhauser effect; examples.Structure elucidation - strategy; combined use of NMR, IR, MS, and UV; selected problems.

Naming of heterocycles; synthesis of pyrroles, furans, thiophenes, imidazoles, oxazoles, pyridines; aromaticity and heteroaromaticity; p-deficient/excessive heterocycles; reactivity of five membered heterocycles; electrophilic substitution; Diels-Alder reactions of furan, pyrrole, thiophene; reactivity of pyridine and pyridine-N-oxide; nucelophilic substitution of pyridine; reactivity of imidazole; structure and reactivity of organolithium reagents; lithiated derivatives of pyrrole, furan thiophene, pyridine.

About this Module

Learning Outcomes:

The ability to apply a combination of Mass Spectrometry, Ultraviolet-Visible Spectroscopy, Infrared Spectroscopy and NMR Spectroscopy (1H and 13C) for structure elucidation.

Indicative Module Content:

Due to the COVID-19 pandemic, the mode of delivery, assessment and content of the module may be subject to change.

Mass Spectrometry - instrumentation; ion production by EI or CI; molecular ion; isotopes; N rule; fragmentation, rearrangement; characteristic processes of different organic classes; applications.Ultraviolet-Visible Spectroscopy - instrumentation; Types of electronic transitions; Conjugation; selected examples. Infrared Spectroscopy - types of vibration; Characteristic vibrations of different functional groups; emphasis on C=O group; applications. NMR Spectroscopy - introduction; CW vs FT NMR; 1H NMR; chemical shift; spin-spin coupling; integration; protons on heteroatoms; magnetic equivalence; AMX, ABX, and ABC spin systems; spin decoupling-1H-1H connectivity ; 13C NMR; decoupling; chemical shifts e.g. aromatic compounds; 2D NMR - 1H-1H connectivity (COSY); 1H-13C connectivity (APT, DEPT); nuclear Overhauser effect; examples.Structure elucidation - strategy; combined use of NMR, IR, MS, and UV; selected problems.

Naming of heterocycles; synthesis of pyrroles, furans, thiophenes, imidazoles, oxazoles, pyridines; aromaticity and heteroaromaticity; p-deficient/excessive heterocycles; reactivity of five membered heterocycles; electrophilic substitution; Diels-Alder reactions of furan, pyrrole, thiophene; reactivity of pyridine and pyridine-N-oxide; nucelophilic substitution of pyridine; reactivity of imidazole; structure and reactivity of organolithium reagents; lithiated derivatives of pyrrole, furan thiophene, pyridine.

Student Effort Hours:
Student Effort Type Hours
Autonomous Student Learning

54
Lectures

18
Tutorial

4
Laboratories

24
Total

100

Approaches to Teaching and Learning:
Lectures, practical classes, tutorial problem sets - Guiry component includes spectroscopic problems on Mass Spectrometry, Infra-red and UV-Vis spectroscopy, NMR 1 and NMR 2. McGarrigle component includes two problem sets on heterocyclic chemistry.

Requirements, Exclusions and Recommendations

Not applicable to this module.


Module Requisites and Incompatibles
Not applicable to this module.
 

Assessment Strategy
Description Timing Component Scale Must Pass Component % of Final Grade In Module Component Repeat Offered
Exam (In-person): The exam will last 2h and will test the students ability to solve problems in modern spectroscopy and heterocyclic chemistry. End of trimester
Duration:
2 hr(s)
 Standard conversion grade scale 40% No
60
 No
Practical Skills Assessment: This module will have 4 experiments related to the material covered in the lectures. Week 5, Week 6, Week 7, Week 8 Standard conversion grade scale 40% No
30
 No
Assignment(Including Essay): Spectroscopy will be assessed by 4 assignments that will be graded and returned to the students at 4 tutorials. The heterocyclic component will have one assignment and one in-class test. Week 2, Week 4, Week 5, Week 6, Week 8, Week 11 Standard conversion grade scale 40% No
10
 No

Carry forward of passed components
Yes
 

Resit In Terminal Exam
Spring Yes - 2 Hour
Please see Student Jargon Buster for more information about remediation types and timing. 

Feedback Strategy/Strategies

• Feedback individually to students, post-assessment

How will my Feedback be Delivered?

There will be a series of class assignments that will be submitted, graded and returned to the students at a tutorial session. For the spectroscopy section of the course there will be an assignment on 1) Mass Spectrometry; 2) IR/UV-Vis Spectroscopy); 3) NMR spectroscopy 1 and 4) NMR spectroscopy 2.

Name Role
Assoc Professor Eoghan McGarrigle Lecturer / Co-Lecturer

Timetabling information is displayed only for guidance purposes, relates to the current Academic Year only and is subject to change.
Autumn Lecture Offering 1 Week(s) - Autumn: All Weeks Mon 10:00 - 10:50
Autumn Lecture Offering 1 Week(s) - Autumn: All Weeks Wed 10:00 - 10:50
Autumn Laboratory Offering 1 Week(s) - 5, 6, 7, 8 Thurs 10:00 - 12:50
Autumn Laboratory Offering 1 Week(s) - 5, 6, 7, 8 Thurs 14:00 - 16:50
Autumn Workshop Offering 3 Week(s) - 3 Mon 14:00 - 14:50
Autumn Workshop Offering 3 Week(s) - 6 Mon 14:00 - 14:50
Autumn Laboratory Offering 3 Week(s) - 5, 6, 7, 8 Tues 10:00 - 12:50
Autumn Laboratory Offering 3 Week(s) - 5, 6, 7, 8 Tues 14:00 - 16:50
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