Module Catalogue

CHY3108 : Advanced Organic Chemistry

  • Offered for Year: 2020/21
  • Module Leader(s): Dr Michael Hall
  • Lecturer: Dr Johan Eriksson, Dr Cristina Navarro Reguero, Dr David Fulton, Dr Hanno Kossen, Dr Michael Carroll
  • Practical Supervisor: Dr Zuleykha McMillan
  • Owning School: Natural and Environmental Sciences
  • Teaching Location: Newcastle City Campus
Semesters
Semester 1 Credit Value: 20
Semester 2 Credit Value: 10
ECTS Credits: 15.0

Aims

To equip students with the necessary knowledge and understanding for them to study organic chemistry at Stage 4; to further enhance the students’ knowledge of the chemistry of aldehydes, ketones, esters, amides and related species; to allow students to design syntheses of compounds containing carbonyl groups; to illustrate the rich and diverse chemistry of the carbonyl group and to show how this can be logically predicted; to introduce the concept of retrosynthetic analysis; to show how the chemistry of the carbonyl unit can be used in total syntheses. To show the importance of carbonyl reactions in enzyme chemistry. To highlight the use of organo-element compounds in the synthesis and reactions of carbonyl compounds.

Outline Of Syllabus

Synthesis of Carbonoyls
Dr DA Fulton

Oxidation of alcohols; chromium (Jones, PCC, PDC), ruthenium (TPAP), Swern, hypervalent iodine and MnO2.
Selective Reductions
Oxidative cleavage of C=C; ozonolysis
Addition of hydrides and carbanions; reaction with carboxylic acids, esters, imines and Weinreb amides
Dithianes (unpolung), Benzoin condensation and MPV reaction

P-block and organometallic chemistry
Dr MJ Hall

General mechanisms for nucleophilic attack on C=O and C=N
Nucelophilic attack of organometallics; synthesis of organometallics and selectivity
Conjugate additions; hard vs soft nucleophiles and the control of 1,2- versus 1,4-addition to alpha,beta-unsaturated carbonyl compounds
P-Block Chemistry Si, S, P, B

Heteroaromatic Chemistry
Dr MA Carroll

Aromatic systems containing heteroatoms; introduction and overview
Membered heteroatromatics containing one heteroatom; pyrroles, furans and thiophenes
Membered heteroaromatics containing one heteroatom; pyridines
Fused heteroaromatics; indoles and quinolines
Heteroaromatics containing more than one heteroatom

Synthesis
Dr MJ Hall

Classical synthesis and synthetic strategy
Retrosynthetic analysis
Protecting group chemistry
Syntheses of specific molecules drawn from the classical and recent literature and covering molecules of theoretical interest, natural products and pharmaceuticals


Organic Chemistry Laboratory Course
Dr Z McMillan
     
Each student pair does the experiments from the following list:
An investigation into the Stereoselectivity of Wittig Reactions
Synthesis of a Queen Honeybee Pheromone
Discovering Selectivity in the Diels-Alder Reaction

Teaching Methods

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

Teaching Activities
Category Activity Number Length Student Hours Comment
Structured Guided LearningLecture materials481:0048:00Online via Canvas - lecture material delivered online via recordings
Guided Independent StudyAssessment preparation and completion130:0030:00Assessment - Preparation and completion of end of semester alternate assessment
Guided Independent StudyAssessment preparation and completion480:5040:00Assessment - Preparation and completion of revision for end of semester alternate assessment
Guided Independent StudyAssessment preparation and completion15:005:00Online - Multiple choice
Guided Independent StudyAssessment preparation and completion120:0020:00Laboratory online assessment
Guided Independent StudyAssessment preparation and completion112:0012:00Laboratory Skills assessment
Scheduled Learning And Teaching ActivitiesPractical26:0012:002 x 6h laboratory sessions supported by online exercises
Scheduled Learning And Teaching ActivitiesWorkshops31:003:00Online retrosynthesis workshops
Scheduled Learning And Teaching ActivitiesDrop-in/surgery161:0016:00Online drop-ins for student questions
Guided Independent StudyIndependent study1113:00113:00Independent study, background reading
Scheduled Learning And Teaching ActivitiesModule talk11:001:00Laboratory induction
Total300:00
Teaching Rationale And Relationship

Lecture materials give students the opportunity to learn advanced concepts in organic chemistry, encompassing synthetic and mechanistic principles. The small group teaching sessions look over these techniques.

In practical classes competencies in practical procedures, observation, record-keeping and report writing, will be taught and learnt.

Assessment Methods

Please note that module leaders are reviewing the module teaching and assessment methods for Semester 2 modules, in light of the Covid-19 restrictions. There may also be a few further changes to Semester 1 modules. Final information will be available by the end of August 2020 in for Semester 1 modules and the end of October 2020 for Semester 2 modules.

The format of resits will be determined by the Board of Examiners

Other Assessment
Description Semester When Set Percentage Comment
Practical/lab report1M33Laboratory online assessment
Computer assessment2M67Alternate assessment and MCQ
Zero Weighted Pass/Fail Assessments
Description When Set Comment
Practical/lab reportMLaboratory Skills assessment
Assessment Rationale And Relationship

The alternate assessment will test the students’ knowledge and understanding of the content of this module in the context of both synthetic and mechanistic chemistry. Formative assessment in the form of coursework will be set in Semester 1.

The laboratory component practical involves the assessment of a complex selection of skills learnt in about 4 experiments per student, spread over the major areas of organic chemistry.

Students are required to obtain at least 35% in the laboratory component in order for the examination mark to be included in the final module mark. Students who score <35% in the laboratory will obtain a module mark based solely on the laboratory practical.

An alternative assessment will be set for any Semester 1 Study Abroad students taking this module, who will not be in Newcastle during the January assessment period

Reading Lists

Timetable