exam_4_prob_key - Exam 4 Extra Problems Key 1 1. Br H O OH...

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Unformatted text preview: Exam 4 Extra Problems Key 1 1. Br H O OH Br O O OH O O Br + H 2 O H 2 O + OH H + O . Et O O O OEt OEt H + Et O O O OEt Et O O + Me O + H OEt O Et O O O OEt H OEt O O Et O O O OEt EtO O O OEt O EtO O O O EtO O O H + OEt O EtO O O O O H 3 O 2. H 3 O + 1. HO + CO 2 A B Figures by MIT OCW. 2 2 O O O O OEt dil. HOAc N C N C NaCN NaCN dil. HOAc H CH 3 CH 3 CH 3 CH 3 CH 3 O OEt H 3 O H 3 O D D HO HO O O O O O OH OH EtO EtO (a) (b) H B OMe 1 1 2 2 3 3 4 4 5 5 O O O OMe OMe OMe O 5 O B H O O O Me Figures by MIT OCW. 3. 4. Massachusetts Institute of Technology 5.13: Organic Chemistry II 5. 3 OTs OTs d- + d H H OH O H + d Only the bond a.p.p. to the LG is involved in these processes. The position of the oxygen determines which product will be formed. Figures by MIT OCW. Only the ring fusion bond is a.p.p. to the LG. OTs OTs HO HO d- + d H H H OTs OTs D OH H OH 2 O O In this "Pinacol- like" concerted process, the migrating bond must be antiperiplanar to the LG so that the oxygen can stabilize the developing change in the TS. This Grob fragmentation is also concerted, so the bond that is cleared must be antiperiplanar to the LG.(only the fusion bond is a.p.p.) Figures by MIT OCW. Figures by MIT OCW. Figures by MIT OCW. Figures by MIT OCW. OH OH2 OTs OTs H H O O H H H O O H H O O H H O O H H O O H O O D H H Massachusetts Institute of Technology 5.13: Organic Chemistry II O O H OMe OMe OMe OMe OMe CF 3 HO H 2 O H 2 O OMe H H 2 O H 2 H 2 O O R Me O H R Me H NH 2 OH Me HO OH R N R R R Me PT N N Me Me OH H N OH H OH of R Me N OH R Me N HO and 6. 7. Each of these mechanisms proceeds through an oxime. (Cont.) Would likely form mixture 4 Figures by MIT OCW. Massachusetts Institute of Technology 5.13: Organic Chemistry II 5 O O O O O N N N N N Me Me OH PCl 5 PCl 5 Ar Ar Ar Ar Ar Ar Ar Ar Ar N N O C Me Me Me Me Me Me Me C H 2 O OH 2 OH 2 OH 2 OH 2 Me Me OH O PT H N N N N H H H ... The methyl group can also migrate. ....
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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exam_4_prob_key - Exam 4 Extra Problems Key 1 1. Br H O OH...

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