Organic Chemistry
CM5121 Graduate Organic Chemistry General Administration Matters
Dr. Zhang Sheng Office no: S7-03-12 Email: chmzs@nus.edu.sg
CM5121
Assessments
CA (quiz, project) 50%
Final Exam (Closed Book)
50%
CA: choose 2 out of 3
Quiz 1 (Week 7, closed book) 25% Quiz 2 (Week 11, closed book) 25% Project Presentation 25% (Week 11-13)
2
Syllabus
Broadly divided into 2 parts: 1) Pericyclic Reactions i) Electrocyclic ii) Cycloaddition and cycloreversion iii) Sigmatropic 2) Rearrangements i) Ring expansion ii) Carbocation rearrangements iii) Pinacol, dienone-phenol, benzilic acid, Favorskii, etc.
3
CA - Quiz
Quiz 1 (week 7, 1 hour) – Revision of fundamental organic chemistry – Sigmatropic, electrocyclic, everything up to week 6. Quiz 2 (week 11, 1 hour) – Pericyclic reactions and rearrangements
4
Revision
Important topics include but not limited to:1) Structure of molecules – Atomic orbitals, molecular orbitals, hybridization 2) Mechanism of reactions – curly arrows, chemical reactions, substitution, elimination, etc 3) Delocalization and conjugation – theory of resonance, structure of alkenes, allyl, vinyl systems. 4) Acidity, basicity and pKa 5) Conformational Analysis - Cyclohexane 6) Stereochemistry – regioselective, stereoselective, stereospecific
5
Examples of Topics covered for Revision Quiz 1 (not limited to the topics below)
1) 2) 3) 4) 5) 6) 7) 8) Acids and Bases Conformations of Alkanes and Cycloalkanes Alcohols and Alkyl halides Elimination Reactions of Alkenes SN1 and SN2 Aromaticity and Electrophilic Aromatic Substitution Aldehydes and Ketones Enols and Enolates
6
Project Presentation
Search the literature for work on pericyclic
reaction or
rearrangement
Make a summary of the work and do a 15 minutes presentation, followed by 5 min Q & A.
Include in your presentation, 1) The journal which your work is based on 2) Upload your ppt slides and journal (in pdf) onto IVLE project submission folder.
7
Dr. Zhang Sheng Office no: S7-03-12 Email: chmzs@nus.edu.sg
CM5121
Assessments
CA (quiz, project) 50%
Final Exam (Closed Book)
50%
CA: choose 2 out of 3
Quiz 1 (Week 7, closed book) 25% Quiz 2 (Week 11, closed book) 25% Project Presentation 25% (Week 11-13)
2
Syllabus
Broadly divided into 2 parts: 1) Pericyclic Reactions i) Electrocyclic ii) Cycloaddition and cycloreversion iii) Sigmatropic 2) Rearrangements i) Ring expansion ii) Carbocation rearrangements iii) Pinacol, dienone-phenol, benzilic acid, Favorskii, etc.
3
CA - Quiz
Quiz 1 (week 7, 1 hour) – Revision of fundamental organic chemistry – Sigmatropic, electrocyclic, everything up to week 6. Quiz 2 (week 11, 1 hour) – Pericyclic reactions and rearrangements
4
Revision
Important topics include but not limited to:1) Structure of molecules – Atomic orbitals, molecular orbitals, hybridization 2) Mechanism of reactions – curly arrows, chemical reactions, substitution, elimination, etc 3) Delocalization and conjugation – theory of resonance, structure of alkenes, allyl, vinyl systems. 4) Acidity, basicity and pKa 5) Conformational Analysis - Cyclohexane 6) Stereochemistry – regioselective, stereoselective, stereospecific
5
Examples of Topics covered for Revision Quiz 1 (not limited to the topics below)
1) 2) 3) 4) 5) 6) 7) 8) Acids and Bases Conformations of Alkanes and Cycloalkanes Alcohols and Alkyl halides Elimination Reactions of Alkenes SN1 and SN2 Aromaticity and Electrophilic Aromatic Substitution Aldehydes and Ketones Enols and Enolates
6
Project Presentation
Search the literature for work on pericyclic
reaction or
rearrangement
Make a summary of the work and do a 15 minutes presentation, followed by 5 min Q & A.
Include in your presentation, 1) The journal which your work is based on 2) Upload your ppt slides and journal (in pdf) onto IVLE project submission folder.
7
References: Text 1) Advanced Organic Chemistry – ‘Reaction and Mechanism’, 2nd ed., Bernard Miller, 2004, Pearson. ( chap. 1, 2, 3, 4, 6 and 8) 2) Organic Chemistry – Clayden, Greeves, Warren and Wothers, 1st ed., 2001, Oxford. ( revise chap. 4, 5, 7, 8, 13 and 18) ( will cover chap. 35, 36, 37, appro. 100 pages) 10 Supplementary • Any Organic textbooks for revision e.g. Paula Bruice (Pearson), McMurray (Thomson). Pericyclic Reactions – Fleming, Oxford. • 11