CHY3105 : Advanced Organic Chemistry (Distance Learning)

Semester 1 Credit Value: 10
Semester 2 Credit Value: 10
ECTS Credits: 10.0


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
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

Nucleophilic addition to C=O
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

Enolate chemistry (This section will be taught in 2017-18)
Dr MJ Hall

Formation of enolates and pKa
Enolate alkylation; O vs C alkylation, kinetic vs thermodynamic control, 1,3-dicarbonyls and the use of malonates in synthesis
The aldol reaction; aldol, dehydration of products, intramolecular aldol and cross aldol
Acylation of enolates; Claisen and Dieckmann condensations
Tandem processes; Darzens, Baylis Hillman, Robinson etc.
Enamines; formation and reactions

Heteroaromatic Chemistry (This section will be taught from 2018-19 onwards)
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

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

Teaching Methods

Teaching Activities
Category Activity Number Length Student Hours Comment
Placement/Study AbroadEmployer-based learning321:0032:00Lecture - Recorded by ReCap and displayed on Blackboard (DL)
Placement/Study AbroadEmployer-based learning1123:20123:20Independent study - Background reading, coursework exercises and practice past exam questions (DL)
Placement/Study AbroadEmployer-based learning320:5026:40Assessment - Preparation and completion of revision for end of semester examination (DL)
Placement/Study AbroadEmployer-based learning115:0015:00Assessment - Preparation and completion of coursework exercises (DL)
Placement/Study AbroadEmployer-based learning13:003:00Assessment - Preparation and completion of end of semester examination (DL)
Teaching Rationale And Relationship

Lectures 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

Description Length Semester When Set Percentage Comment
Written Examination1802A100N/A
Exam Pairings
Module Code Module Title Semester Comment
CHY3108Advanced Organic Chemistry2N/A
Assessment Rationale And Relationship

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

Students sit the examination on their return to Newcastle for one week during the Semester 2 examination period.

Reading Lists