CHEM30210 Structure Determination and Aromatic Heterocyclic Chemistry

Academic Year 2022/2023

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.

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Curricular information is subject to change

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
Lectures

18

Tutorial

4

Laboratories

24

Autonomous Student Learning

54

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 Open Book Exam Component Scale Must Pass Component % of Final Grade
Examination: Written examination 2 hour End of Trimester Exam Yes Graded No

60

Continuous Assessment: various assessments over the semester Varies over the Trimester n/a Graded No

10

Lab Report: Laboratory, continuous assessment. Varies over the Trimester n/a Graded No

30


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