Notes for CHM249
The notes provided on this page are part of the course material. You should bring them to class. They do not however act as a substitute for attending the class, since there will be additional material covered in class that does not appear in these notes. In addition, I will emphasize particular sections from these notes. Finally, much of the material we will cover will not have an associated handout.
The notes given below are password protected, and are available to students taking the class. The username and password can be obtained from your lecturer during lectures or office hours.
Introductory Review (WEEK 1)
Summary of First Year Organic Chemistry: The "Top Ten" List
Overview of Arrow-Pushing Principles and Problems to solve. This document contains a summary of electron-pushing and common problems encountered, as well as a problem set. This is arguably the most important problem set you will get in the course. Spend time working over this - it is non-trivial. Most of the reactions shown you have not seen before - do not worry about this, instead focus on the rules of curved arrow-pushing. Although curved arrows should be regarded as a formalism, once you have mastered these rules, they will allow you to interpret any organic reaction. Since these rules are not intuitive, you should expect to make mistakes in applying them at first. I would suggest working on this problem set individually at first. Then look at the answers that will be posted next week. Then form a study group and discuss any problems or questions you may have. Of course, come and see me during office hours if you have questions at any point. Also, the relevant sections in the textbook are in chapter 1 (sections 1.5-1.12) and chapter 2 (sections 2.1-2.4, 2.6, 2.11 and 2.12). Again I should stress that once you have mastered this aspect of organic chemistry, the subject becomes much easier to learn.
Answers to Arrow-Pushing Problems
Application of IR and NMR Spectroscopy (WEEK 1-4)
1H NMR Correlation Tables (This is provided to you in Exams)
13C NMR Correlation Tables (This is provided to you in Exams)
Electronegativity & Chemical Shifts & A Useful Chart! (NEW!!!)
Spectroscopy Problem Set for Week 3
Answers to Spectroscopy Problem Set for Week 3
Spectroscopy Notes 4 Spectroscopic problems to be solved in class
Spectroscopy Problem Set for Weeks 3/4 - 1st Set
Spectroscopy Problem Set for Week 3/4 - 2nd Set
Answers to Spectroscopic Problems for Weeks 3/4 (both sets)
Electrophilic Aromatic Substitution
Applications of Electrophilic Aromatic Substitution
Nucleophilic Aromatic Substitution
Summary of Diazonium Salt Chemistry
Alkynes - Synthesis and Reactivity
Alcohols / Ethers and Oxidation Chemistry
Organolithium and Organomagnesium Chemistry
Synthetic Targets: Retrosynthetic Analysis. (please note that this problem set is quite challenging and it will require some time for you to complete!
Synthetic Targets/Retrosynthetic Analysis - Sample Answers.
Additions of Strong Nucleophiles to Aldehydes and Ketones
Other Transformations of Aldehydes and Ketones
Two Natural Product Synthesis Examples
Acids and Derivative (Notes 1)
Acids and Derivative (Notes 2)
Acids and Derivative (Notes 3)
Miscellaneous Amine and Rearrangement Reactions
Enolates and Alkylation (NEW!)
Enolates: Condensation Reactions, Michael Additions and Syntheses (NEW!)
Summary Overview of Synthetic Planning and Reactions (NEW!)
Pericyclic Reactions (NOT COVERED) (NEW!)
Additional Problems: Suggested Problems from Textbook on Spectroscopy (Chapter 13): 13.17, 13.32, 13.33, 13.43, 13.48, 13.53, 13.56, 13.57, 13.60.
Suggested structure determination probelms from "WebSpectra" site: "Beginning" Problems 17, 12, 4, 25, 19, 26, 30. Please note that working through these problems may require some time. Also, note that in the 13C spectra, a signal (triplet) centred at 77.0 ppm is due to CDCl3 which is used as the NMR solvent.
Another useful site for NMR problems: Organic Structure Elucidation
Aromatic Chemistry (WEEKS 4-6)
Suggested Problems from Textbook on Aromatics (Chapter 16): 35, 36, 39, 40, 42 to 48, 53, 56, 60, 69, 70, 73
Chemistry of Alkynes, Alkenes and Alcohols (WEEKS 7-8)
Suggested Problems from Textbook (Chapter 10): 12, 13, 21, 23, 42
Suggested Problems from Textbook (Chapter 11): 4, 5, 29, 33, 47, 62, 66, 67, 68
Suggested Problems from Textbook on Alcohols (Chapter 17): 7, 10, 30, 33, 34, 44, 49, 57, 59, 62
Suggested Problems from Textbook on Ethers (Chapter 18): 15, 27, 30, 43, 52
Chemistry of Aldehydes and ketones (WEEK 9)
Suggested Problems from Textbook on Aldehydes and Ketones (Chapter 19): 33, 37, 38, 41, 45, 51, 67
Organic Synthesis Examples (WEEK 10)
Carboxylic Acids and Derivatives Notes (WEEKS 10-11)
Suggested Problems from Textbook on Carboxylic Acid Derivatives (Chapter 20): 5, 26, 28, 38, 39, 46, 49
Suggested Problems from Textbook on Carboxylic Acid Derivatives - Substitution (Chapter 21): 5, 13, 22, 36, 37, 52, 53, 54
Acidity/Basicity and Amines (WEEK 12)
Suggested Problems from Textbook on Amines (Chapter 24): 30, 45, 50, 59, 65, 66
Enolate Chemistry (WEEKS 12-13)
Suggested Problems from Textbook on Enolates (Chapter 22): 7, 11, 14, 17, 23, 24, 29, 37, 38, 44, 53
Suggested Problems from Textbook on Enolate Condensations (Chapter 23): 28, 29, 36, 42, 45, 46, 51, 56, 57
SUMMARY OF REACTIONS AND SYNTHETIC PLANNING
Pericyclic Reaction Notes (NOT COVERED & NOT ON FINAL EXAM)
Please note that this material will not be covered in the lectures, and it will NOT appear in the final exam for 2008. It is included for your interest. However, there are some questions (given below) on previous final examinations that did utilize these reactions.
Final Exam 2005: Question 1h
Final Exam 2004: Question 2 - the last reaction
Extra Exam Prep: Question 12c
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