Global Opportunities

CHY3108 : Advanced Organic Chemistry (Inactive)

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
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
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
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
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      
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

Teaching Activities
Category Activity Number Length Student Hours Comment
Structured Guided LearningLecture materials481:0048:00PiP lectures. Online lectures in case no PiP due to social distancing regulations.
Guided Independent StudyAssessment preparation and completion149:0049:00Assessment - 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
Scheduled Learning And Teaching ActivitiesPractical510:0050:00lab sessions with online exercises as backup.
Scheduled Learning And Teaching ActivitiesWorkshops31:003:00Online retrosynthesis workshops
Scheduled Learning And Teaching ActivitiesDrop-in/surgery161:0016:00PiP drop-ins for student questions or online in case no PiP due to social distancing regulations.
Guided Independent StudyIndependent study193:0093:00Independent study, background reading
Scheduled Learning And Teaching ActivitiesModule talk11:001:00Laboratory induction
Total300:00
Jointly Taught With
Code Title
CHY3105
CHY3111Advanced Organic Chemistry
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

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

Exams
Description Length Semester When Set Percentage Comment
PC Examination1802A67Computer based MCQ and long answers or online assessment as alternative in the case of no PiP examinations
Exam Pairings
Module Code Module Title Semester Comment
CHY3105Advanced Organic Chemistry (Distance Learning)2N/A
CHY3111Advanced Organic Chemistry2N/A
Other Assessment
Description Semester When Set Percentage Comment
Practical/lab report1M33Laboratory online assessment
Zero Weighted Pass/Fail Assessments
Description When Set Comment
Practical/lab reportMLaboratory Skills assessment
Assessment Rationale And Relationship

The exam 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