Problem Set 2 Solution

Gave mostly full credit depending on the phrasing 1

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Unformatted text preview: redit: - state that the structure of 1 and 2 are different and point out the difference Name Ch 1b, Problem Set Two Section Side 5 of 6 Due Friday, Jan. 24, 2014 Rec TA at 4 PM PST in the Drop Box - state that this structural difference leads to the lack of resonance stabilization in 2 - state that this feature makes decarboxylation of 2 slower/less favorable In other words, the double bonded nitrogen, known as an imine, provides resonance stabilization in molecule 1 (it stabilizes the negative charge that forms on the product). In molecule 2, the lack of such a motif prevents the decarboxylation reaction from readily occurring. 5 points c. For full credit: - state that the difference between 1 and 3 is the presence of CF3 group - state that CF3 is a strong electron withdrawing group - state that its presence stabilizes the negatively charged product (via inductive effect) The effect of CF3 is NOT making the deprotonation step easier; it also isn’t really the point that the C-C bond is now weaker, but it is true that product stabilization makes the bond “weaker”. Gave mostly full credit (depending on the phrasing) 1 point for faster, 4 points for why 8. (20 POINTS) When ethyl acetate is reacted with strong base, two molecules of ethyl acetate react with each other to...
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