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Module

CHY3105 : Advanced Organic Chemistry (Distance Learning)

  • Offered for Year: 2021/22
  • Module Leader(s): Dr Michael Hall
  • Lecturer: Dr Johan Eriksson, Dr David Fulton, Dr Michael Carroll
  • Owning School: Natural and Environmental Sciences
  • Teaching Location: Newcastle City Campus
Semesters
Semester 1 Credit Value: 10
Semester 2 Credit Value: 10
ECTS Credits: 10.0

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 Cardonoyls
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

Teaching Methods

Teaching Activities
Category Activity Number Length Student Hours Comment
Guided Independent StudyAssessment preparation and completion130:0030:00Assessment - Preparation and completion of end of semester alternate assessment (DL)
Guided Independent StudyAssessment preparation and completion480:5040:00Assessment - Preparation and completion of revision for end of semester alternate assessment (DL)
Guided Independent StudyAssessment preparation and completion163:0063:00Independent study - Background reading, coursework exercises and practice past exam questions (DL)
Placement/Study AbroadDL on Placement 481:0048:00Lecture - online material via Canvas
Scheduled Learning And Teaching ActivitiesWorkshops31:003:00Online retrosynthesis workshops
Scheduled Learning And Teaching ActivitiesDrop-in/surgery161:0016:00Online drop-ins for student questions
Total200:00
Jointly Taught With
Code Title
CHY3108Advanced Organic Chemistry
CHY3111Advanced Organic Chemistry
Teaching Rationale And Relationship

Lectures materials are delivered electronically and these bring together advanced concepts in organic chemistry, encompassing synthetic and mechanistic principles. Student learning is supported by the provision of worksheets which are returned with formative feedback.

Assessment Methods

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

Exams
Description Length Semester When Set Percentage Comment
PC Examination1802A100Computer based MCQs and long answers. Online assessment as alternative in the case of no PiP examinations.
Exam Pairings
Module Code Module Title Semester Comment
CHY3108Advanced Organic Chemistry2N/A
CHY3111Advanced Organic Chemistry2N/A
Assessment Rationale And Relationship

The exam will test the student's knowledge and understanding of the content of this module in the context of both synthetic and mechanistic chemistry.

Reading Lists

Timetable