Chem 634 Professor Fox Practice Questions for exam 2 1 Provide a mechanism H 2N H2N H H H H 2N H2N H H 2N H indicates the position of a carbon atom in an allene structure H H Workup using H2 O reaction driven by the stability of the terminal acetylide 2 Provide a mechanism and propose a structure for intermediate 3 CH3 4 equiv BuLi Me MeOTs C5Li 4 Me 3 Me Me 3 Li H H H Bu Li Bu Li 2 Li Me Me Me MeOTs Me Bu Li H Li Li H 4 Li Li Li Bu Li 3 Provide a mechanism pts Ph O Ph NHMe O CHO O Ph Me H N Me Ph Ph NH H N OH Me O O O H2O H H N Me N Me O enolize H O H Ph Ph Ph Ph N Me HO N H Me N Me O 4 Provide a mechanism 20 pts CH3 CH3 Pd PPh3 4 I H K2 CO 3 H OMe OMe Pd 0 CH3 I Pd PdI alkene insertion H CH3 CH3 PdI hydride H elimination H CH3 alkene insertion H H OMe OMe OMe OMe 5 Propose a synthesis using any materials with 6 carbons or less 20 pts H O O H H N O CuMgBr 2 O then MeI Me H2N NH2 KOH diglyme H cat PdCl2 cat CuCl2 O2 H2O Me O H Me
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