Module Catalogues, Xi'an Jiaotong-Liverpool University   
Module Code: CHE201
Module Title: Intermediate Organic Chemistry
Module Level: Level 2
Module Credits: 5.00
Academic Year: 2017/18
Semester: SEM1
Originating Department: Chemistry
Pre-requisites: N/A
The aim of this module is to introduce important carbon-carbon bond forming reactions within a mechanistic and synthetic framework, together with exposure to a selection of stereochemical issues.
Learning outcomes 
Students should be able to solve problems featuring:

- Scope and mechanisms of basic reactions (nucleophilic and electrophilic substitutions, addition and elimination reactions)

- Basic carbonyl chemistry (alkylation, acylation, aldol, conjugate additions).

- Structure, reactivity and synthesis of simple heterocycles (including pyridines, pyrroles, furans)

- Functional group interconversions and stereochemistry.
Method of teaching and learning 
The theory part of this module will be delivered through a series of lectures to be given throughout the first semester. The material presented at the lectures is supported by tutorials.
1. Conjugate addition and nucleophilic aromatic substitution: Conjugate addition: conjugation of alkenes with electron-withdrawing groups makes them electrophilic and allows nucleophilic attack. Conjugate substitution: electrophilic alkenes bearing leaving groups can promote substitution reactions at C=C related to those at C=O. Nucleophilic aromatic substitution: electron-poor aromatic rings that allow substitution reactions with nucleophiles rather than the usual electrophiles. Special leaving groups and nucleophiles that allow nucleophilic aromatic substitution on electron-rich rings.

2. Chemoselectivity and protecting groups: Regio-, stereo-, and chemoselectivity. Reagents for reduction of alkenes and carbonyl compounds. Removal of functional groups. Reduction of benzene rings. Reagents for oxidation of alcohols. Reagents for oxidation of alkenes. Protection of aldehydes, ketones, alcohols, and amines. Synthesis of peptides.

3. Regioselectivity: Selectivity of a new kind decided by mechanism. Reagent and substrate are both important. Controlling the arrangement of aromatic substituents. How to get ortho selectivity: ortholithiation and sulfonation. Radical as well as anionic reactions. Reactions of allylic compounds. Revisiting conjugate addition.

4. Alkylation of enolates: How to make C-C bonds using carbonyl compounds as nucleophiles. How to prevent carbonyl compounds reacting with themselves.

5. Reactions of enolates with carbonyl compounds: The aldol and Claisen reactions: Reactions with carbonyl compounds as both nucleophile and electrophile. How to make hydroxy-carbonyl compounds or enones by the aldol reaction. How to be sure that you get the product you want from an aldol reaction. The different methods available for doing aldol reactions with enolates of aldehydes, ketones, and esters. How to use formaldehyde as an electrophile. How to predict the outcome of intramolecular aldol reactions. How esters react with enolates:
Delivery Hours  
Lectures Seminars Tutorials Lab/Prcaticals Fieldwork / Placement Other(Private study) Total
Hours/Semester 26     26      98  150 


Sequence Method % of Final Mark
1 Written Examination 70.00
2 Continuous Assessment(Tutorials) 15.00
3 Assignments 15.00

Module Catalogue generated from SITS CUT-OFF: 10/22/2017 9:38:27 PM