View source for Talk:Mod:db9127organic

1.1  Energies good. Why is the exo- isomer more stable than the endo?  A diagram of the secondary orbital overlaps would have been good.  The reaction is hydrogenation, not hydrolysis!

1.2 Your structure for 5 looks OK – but what is its energy? Why does the Me attack cis to C=O?  What was the energy for 7?  Are there any other possible conformers?  In this case, the nucleophile doesn’t coordinate to the C=O…so how do you explain the stereochemical outcome?

1.3 Your ChemDraw drawing of 11 is essentially impossible!!  It’s a pity you haven’t included your modelled structures. The energy of 10 is way too high – do any of the bond angles look strange?   You haven’t really explained why the alkene reacts slowly. 

1.4 Structures look fine, but what were their energies?

1.5 What do the C=C stretch frequencies tell you about the exo-alkene?

Mini-project: You should have compared the calculated values to the lit ones (ideally quantifying the correlation in some way). 


Overall – you managed most of the modelling OK, but could have put a bit more thought into the interpretation and presentation. There are some key missing structures and energies.