hey weiss, i'm glad your staying away from the stuff at this time. i am too for now, but have a lot of people asking me at school (alot of them juice, so when a friend asked me last summer i too started to research for a safer alternative). i think you are going about it the wrong way. i know that one can do all sorts of calculations (i've taken alot of organic and physical chem during my biochem degree) but all those figures already exist. i will try to hunt them down tomorrow. unfortunately the reaction is not promising because other compounds are formed one is a pregnelone. as for acetic acid get glacial, its like 99%. if you live in a large city you could get it from a chemical supply company. as for weiss, you could probably get it at school (join the science club and do an experiment preferably one that requires lots of acetic acid, then make sure alot more is ordered and borrow some).
enthalpy is the bond energies of the bonds in question, entropy is not a factor since the two positions would have the same process take place. the only reason we have to worry about enthalpy is that if we use too strong an oxidizing agent, then both OHs will become ketones (we would be making androstenedione). the testosterone molecule however, is not aromatic, it only has one double bond. when it aromatizes it becomes an estrogen in which the A ring is aromatic. as for the strength of the bonds between C and O i believe that the 17 position is stronger, here's why: even though the ring at 17 has only 5Cs, it is adjacent to a quatrenary carbon which is very stable, also the adjacent carbon to C3 has a double bond which actually helps to destabilze the C-O bond and when C=O forms it will then be able to form a resonance with the double bond (though not to the degree of an aromatic ring).
just trust me for now, i will get the data as soon as possible and if i'm wrong i'll tell. as for going through complicated math, don't bother, there is an easier way i'm sure. i will try to post all the thermodynamic data so we can all be on the same page. i will also keep looking through the synthesis manuals i'm sure the reaction will probably be there too.
weiss talk to me before you do any long calculations, i can probably find the data in the critical tables which will be better than an approximation. also the reaction will not require extreme conditions, it will be in room temp in water (all good process chemists try to make all reactions such - i am not a process chemist). by the way weiss you were on the right track except for the bond strengths, good work, for a young'un your pretty sharp.
BTW this process will work for 19nor4androstenediol --> nandrolone