[azmanam]

Copying this over from the Chemistry Blog[1] for posterity/search engine results here on the forums.  Blogger Jeremy[2] posts a list of 9 Common Student Difficulties in Organic Chemistry he found while setting up his classroom as a new professor. 

   1. Lack of organization
   2. Difficulty in keeping up with lecture while taking notes
   3. Failure to finish exams
   4. Inability to manipulate three-dimensional structures on paper
   5. Too little drill – lack of repetitive practice
   6. Falling behind
   7. Poor problem analysis
   8. Inability to see and mentally manipulate three-dimensional objects
   9. Insufficient energy and/or motivation for the challenges of this course

The tips sheet concludes:
"If you start to get into trouble in this course review this sheet.  Knowing what has gone wrong allows you to fix it."

[1] http://www.chemistry-blog.com/
[2] http://www.chemistry-blog.com/author/starless127

[azmanam]

In the comments[1], I[2] added my 6 Truths of Organic Chemistry that I have derived from tutoring a 15-20 students over 10 semesters of graduate school.  I will likely be sharing my list with my students when I start as a new faculty member in the fall.

#1) Approach unknown reactions just like you should approach all reactions
– Identify nucleophile(s)
– Identify electrophile(s)
– Nucleophiles attack electrophiles
– Repeat

#2) Weaker Acid Wins
– In and acid/base equilibrium, the equilibrium favors the side of the arrow with the weaker acid (the compound with the higher pKa)

#3) Mind your charges
– Make sure the net charge of all compounds is consistent throughout a mechanism

#4) The 2nd Best Rule
– The 2nd best resonance structure usually defines a functional group’s reactivity

#5) Carbonyls: THE CODE
– There are only 3 elementary steps in a carbonyl addition mechanism.
1) Proton Transfer (always reversible)
2) Nucleophilic Addition to a Carbonyl (electrons go up onto oxygen)
3) Electrons Collapse Down from Oxygen (and kick out a good leaving group.
The steps can be in any order and repeated, but those are the only 3 steps needed for addition to acid chlorides, acid anhydrides, aldehydes, ketones, amides, esters, and carboxylic acids (including aldol and Claisen reactions)

#6) When in doubt: Number Your Carbons!
– When coupling 2 molecules, if it not readily obvious where the various atoms go in the product, number the carbon atoms in the starting material and map those numbers on to the product.

[1] http://www.chemistry-blog.com/2010/07/13/common-student-difficulties-in-organic-chemistry/#comments
[2] http://www.chemistry-blog.com/author/azmanam