So you say either a graduate degree in organic chemistry or masters to be able to write out mechanisms as fluently as he does in most of his videos? I was guessing around the same thing too.
I'm currently trying to gather enough resources, and come up with weekly homework assignments and biweekly review assignments to accompany a full organic chemistry I & II (undergraduate) curriculum for myself.
I can find just about everything I need except the hard part is getting worksheets that fit perfectly. I figure around 380 topics from start to finish, do 6 topics a week with homework & practice & review should equal 66 weeks and I will know about as much as an undergraduate. I'd like to aim more towards a graduate though within that timespan. I have enough free time. I'm also trying to gather resources to learn the calculus needed to go along with it. It's kinda hard to put a good curriculum together
I've found this:
http://www.colby.edu/chemistry/OChem/CH241/syllabus.html (organic chem I)
http://www.colby.edu/chemistry/OChem/CH242/syllabus242.pdf (organic chem II)
I have the following books to use:
SOLOMONS Fundamentals of Organic Chemistry 4th Ed
Organic Chemistry by Clayden, Greeves and Warren. 2nd Ed (with solutions manual to accompany)
A LOT of online PDF's downloaded.
One of the math ones that look really good is called: The Chemistry Maths Book by Erich Steiner