Module Catalogues, Xi'an Jiaotong-Liverpool University   
Module Code: CHE303
Module Title: Advanced Organic Chemistry
Module Level: Level 3
Module Credits: 5.00
Academic Year: 2018/19
Semester: SEM1
Originating Department: Chemistry
Pre-requisites: N/A
The aim of the course is to consolidate and extend second year knowledge of synthetic and physical organic chemistry, and introduce some aspects of biological chemistry.
Learning outcomes 
A: Students should be able to solve problems featuring:

- Pericyclic reactions: cycloadditions; Pericyclic reactions: Sigmatropic and electrocyclic reactions.

B: Students should be able to solve problems featuring: Radical reactions; Rarrangements and Fragmentations; Synthesis of alkenes -- controlling double bond geometry

C: Students should be able to solve problems featuring: Physical organic chemistry and bioorganic chemistry
Method of teaching and learning 
A series of lectures will introduce the main theories and concepts, which will be explored in the supporting tutorials.
1. Pericyclic reactions: cycloadditions
• The rules that govern cycloadditions
• Photochemical reactions: reactions that need light
• Making six-membered rings by the Diels–Alder reaction
• Making four-membered rings by [2 + 2] cycloaddition
• Making five-membered rings by 1,3- dipolar cycloaddition
• Using cycloaddition to functionalize double bonds stereospecifically
• Using ozone to break C=C double bonds

2. Pericyclic reactions: Sigmatropic and electrocyclic reactions
• Stereochemistry from chair-like transition states
• Making γ,δ-unsaturated carbonyl compounds
• What determines whether these pericyclic reactions go ‘forwards’ or ‘backwards’
• Fischer Indole synthesis
• Why substituted cyclopentadienes are unstable
• What ‘con’- and ‘dis’-rotatory mean
• Reactions that open small rings and close larger rings
3. Rear3: Rarrangements and Fragmentations
• Participation means acceleration and retention of stereochemistry and may mean rearrangement
• Participating groups can have lone pairs or π-electrons
• Carbocations often rearrange by alkyl migration
• Ring expansion by rearrangement
• Using rearrangements in synthesis
• Electron donation and electron withdrawal combine to create molecules that fragment
• Anti-periplanar conformation is essential
• Small rings are easy to fragment, medium and large rings can be made in this way
• Double bond geometry can be controlled
• Using fragmentations in synthesis
4. Radical reactions
• Radical reactions follow different rules to those of ionic reactions
• Bond strength is very important
• Radicals can be formed with Br, Cl, Sn, and Hg
• Efficient radical reactions are chain reactions
• There are electrophilic and nucleophilic radicals
• Radicals favour conjugate addition
• Cyclization is easy with radical reactions
Delivery Hours  
Lectures Seminars Tutorials Lab/Prcaticals Fieldwork / Placement Other(Private study) Total
Hours/Semester 26     13      111  150 


Sequence Method % of Final Mark
1 Final Exam 60.00
2 Class Test 1 15.00
3 Class Test 2 15.00
4 Coursework 10.00

Module Catalogue generated from SITS CUT-OFF: 5/22/2018 9:58:07 PM