Jump to content

Talk:Module1:scastiglione1

From ChemWiki

Cp: Your structures and energies are fine (although too many dec places!) Analysis is generally good. You're right that the Diels-Alder is stereospecific, but it's not really relevant here because both components are cyclic! A diagram to illustrate the secondary orbital interactions would have been good. Note that a higher energy for 3 relative to 4 does NOT mean that it has to be the kinetic product - it would be perfectly possible for 4 to be preferred both kinetically AND thermodynamically.

NAD: Structure 5 looks fine, but 6 (which wasn't needed anyway) has one VERY odd carbon! Analysis good. Structure 7 also good.

Taxol: structures and energies are great. Can you explain the low reactivity of the olefin in terms of structural interactions, rather than orbitals?

CCl2: excellent

Mini-project: (Your intro seems rather familiar...) Choice of molecules good. I would expect the highest ppm peak in the 13C to be the carbonyl group. Sometimes quaternary carbons like this are difficult to see in the 13C spectrum (low intensity), so it's possible the carbonyl/some quaternary aromatics are missing in the lit data. If you move your lit values down 3 or 4 places in the comparison table to account for this, it all seems to match rather better! I wouldn't have bothered calcuating 1H, IR or optical rotation as they are not likely to help prove the alkene geometry. The best choice would be NOEs.

Overall - a very good effort, and well presented