[SirReal]

Hello there,

My ogranic chemistry book is not the best, and my professor is even worse.  Thus, I am teaching myself organic chemistry from the internet.  However, I am cursed by a horrid affliction in which I want to understand everything as fundamentally as possible (and to visualize it in 3D space).  Therefore, picturing the idea of resultant stereocenters in alcohol synthesis from a cyclic ketone, using an organometallic or Grignard reagent, has been quite a fascination for me.  I have gotten to the point where I can draw out all of the reaction mechanims and predict products- except for cyclic aldehydes which DO NOT HAVE SUBSTITUENTS (unless we are counting hydrogen).  For example, see attachments.

In the example, my book says that this will produce a product in which the resultant hydroxide group is equitorial.  How can this be predicted?  It makes mention of steric hindrance by topside hydrogens, but why does this mean that the hydroxide group will form equitorial?  Why does it not form axial?  Does it involve the poor energy state of axial substituensts?