New Release: Unit 14 Nomenclature Part B & Unit 15 Conjugation and Aromaticity are now available for purchase through the site. You can purchase the Semester 1 book for $40 at the Organic Chemistry Stores (W1-22) of the University of Alberta.

Should You Review Before Semester 2?

Success in Organic Chemistry Semester 2 hinges on your mastery of key Semester 1 topics. Refresh your understanding of electron-pushing, resonance, and organic acid-base reactions to excel.

How you do in Semester 2 depends entirely on how well you did in semester 1 AND how long ago you took it.   Most professors will expect you to remember and be very comfortable with core  semester 1 material (and they will rarely review it.).  If you were a master of organic chemistry in semester 1 and you finished it 1 or 2 months ago you can just walk into semester 2.  

BUT many people have a summer or much longer gap between semesters.  Organic chemistry is like a language; if you haven’t properly learned and practiced it lately you will struggle.  

If you never really learned semester 1 in the  1st place then you will be lucky to get the same grade in semester 2.   If you got below a B you will likely slip in grade unless you do remedial work. 

Here are the 3 most important areas from semester 1 to know.  They are in decreasing order of importance but knowing all 3 will give you a solid start to the semester. My book will rapidly and efficiently teach you these topics but you can learn/relearn them on your own.    

1. Electron-pushing, resonance, organic acid-base reactions and basics of mechanism  

You may remember  from semester 1 that you can easily remember the large number of organic chemistry reactions if you know their mechanisms.  To know mechanism you have to understand how electron-pushing arrows work. Organic acid and base reactions are an easy-to-understand way to illustrate the basics of how organic molecules react. Even learning/relearning this one section will be a huge advantage.   


6.1 Resonance and Electron-Pushing Rules
6.2 Energetics (Skip)
6.3 Organic Acids and Bases
6.4 Trends in Acidity:  Electronegativity, Resonance and Inductive Effects
6.5 Electrophiles, Nucleophiles and Mechanism Defined  

2. Alkene Reactions

The essential alkene reactions (e.g. the Markovnikov reaction of HBr) are so important  that many people start studying them even in high school.  Look for a  “cheat sheet” of essential alkene reaction in 8.4.  Some of these reactions will definitely turn up in semester 2.  


8.1 Unsymmetrical Additions: HX, H2O and Markovnikov’s Rule
8.2 Symmetrical Additions: X2, H2, 1,2-Dihydroxylation and Epoxidation 
8.3 Oxidative Cleavages with Hot KMnO4 or O3: Carbonyl Products 
8.4 List of Essential Alkene Reactions 
8.5 List of Reactions to Synthesize Alkenes 

3. Alcohol Reactions

Alcohols are used and made constantly in semester 2 so you need to be very comfortable with them.  Again look for the “cheat sheet” of essential reactions in 10.5.   


10.1 Acid-Base Reactions of Alcohols 
10.2 Conversion to Good Leaving Groups: Alkyl Halides and Sulfonates 
10.3 Substitution Reactions: Ether Synthesis and Protecting Groups   
10.4 Dehydration Reactions: Synthesis of Alkenes 
10.5 List of Essential Alcohol Reactions   
10.6 List of Reactions to Synthesize Alcohols  




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