Ch 17-18 anwsers - OCH 3 O H 3 CH 2 C CH 3 MgBr H 3 O + 1)...

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Review questions on Chapter 17 & 18 (Alcohol & Ether ): Give the structure (or reagent) in the box: H 3 CH 2 C CH 3 H OH TsCl, pyridine NaCN (S N 2) H 3 CH 2 CC H OH CH CH 3 CH 3 H 2 SO 4 one major pdt possible minor pdt (dehydration) + 1. 2. 3. 4. OH 5. 6. OC H 2 CH 3 + 7. OC H 2 CH 3 HBr (excess) 8. O HI (excess) 9. H 3 CH 2 C CH 3 H OH SOCl 2 OH Br CN H 3 CH 2 CC H OH CHCH 3 CH 3 PCC Cl CH 3 H CH 2 CH 3 H 3 CH 2 C CH 3 H OTs NC CH 3 H CH 2 CH 3 H 3 CH 2 CC HCC H 3 CH 3 H 3 CHC CH CH CH 3 CH 3 PBr 3 NaCN, DMF POCl 3 pyridine H 3 CH 2 CC O CH CH 3 CH 3 ONa CH 3 CH 2 Br CH 3 CH 2 Br OH and
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Epoxide Formation: Ring opening of epoxide under acidic conditions: Ring opening of epoxide under alkaline conditions: Reaction of epoxide with Grignard Reagents: Cl 2 , H 2 O HO Cl NaOH O O H 3 CH 2 C H + CH 3 OH OH H 3 CH 2 C H 3 CO O H 3 CH 2 C CH 3 ONa CH 3 OH H 3 O + 1) 2) OH H 3 CH 2 C
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Unformatted text preview: OCH 3 O H 3 CH 2 C CH 3 MgBr H 3 O + 1) 2) O CH 3 CH 2 MgCl H 3 O + 1) 2) OH H 3 CH 2 C CH 3 OH CH 2 CH 3 Design a synthesis O OH from to give OH (A) (B) (C) OH (D) OH O OH NaBH 4 Br MgBr CH 2 OH CH 2 CH 2 OH OH H 3 C 1. CH 3 MgBr 2. H 3 O + PBr 3 Mg, ether 1. HCH=O 2. H 3 O + 2. H 3 O + 1. O Design a synthesis from HO CH=O to HO O TMSO CH=O TMSO CH 2 OH TMSO CH 2 Br TMSO CH 2 MgBr TMSO OH TMS-Cl Et 3 N NaBH 4 PBr 3 Mg ether 1. CH 3 CH=O 2. H 3 O + H 3 O + PCC TMSO O...
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This note was uploaded on 03/29/2008 for the course CEM 252 taught by Professor Rathke during the Spring '08 term at Michigan State University.

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Ch 17-18 anwsers - OCH 3 O H 3 CH 2 C CH 3 MgBr H 3 O + 1)...

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