Chem 317 - Set 2 extra problem Solutions

Chem 317 - Set 2 extra problem Solutions - Need a different...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
Chemistry 317 Problem Set 2. Solutions Cl OH OH OH O OH CH 3 A B C D Br HO F 1. a) (E) 5,6-dimethylhept-4-en-1-ol b) (1S, 4R)-4-chlorocyclohex-2-en-1-ol 2. a) inductive effect b) solvation 3. E G MgBr O H 2 O C OH HO OH OH PCC A B HO O O HO O O OH OH O 18 OH H 2 SO 4 A O 18 O OH Br D: PBr 3 O O O NaBH 4 A B O OH O OH OH a. A: Br 2 , light B: Mg, ether b. CrO 3 /H + c. + d. A: Br 2 , light B: KOtBu C: Hg(OAc) 2 /H 2 O e. LAH 4. Complete the following reactions or reaction sequences:
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
OH H 3 CO OCH 3 A NaBH 4 B O H 3 CO OCH 3 O OH H 3 CO OCH 3 OH OH A: Na 0 O - Na + OTs B O Br OH O OH OH Br OH Br OTMS O OH OH OH OCH 3 OH Cl O 1. CH 3 MgBr CHO CH 3 HO CHO O OH CH 3 HO CHO O CH 3 HO CHO OH MgBr O Br Mg ether 5a. 1. can't make a Grignard with an OH present in the alkyl halide. 2. need to quench the reaction with H 2 O to isolate alcohol. Mg ether 1.H + /H 2 O 2. F - TMSCl/ Et 3 N 1.NaOH 2. CH 3 I b. can't deprotonate an alcohol with NaOH. Use Na o or NaH instead. HCl 25 ˚C c. S N 2 reaction is too slow at 25 ˚C; this would require heat; better to use SOCl 2 instead of HCl. d. 2. H 2 O no selectivity of Gignard for ketone over aldehyde.
Background image of page 2
Background image of page 3
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Need a different starting material. 1. TMSCl/Et 3 N 2. CH 3 MgBr 3. H 2 O 4. F-5. PCC OR 1. CH 3 MgBr 2. H + /H 2 O 3. O 3 /(CH 3 ) 2 S + Mg/ether 1. react 2. H + /H 2 O + HBr 25 C 1. BH 3 THF 2. NaOH/H 2 O 2 3. H 2 /Pd(C) 4. PCC 6a. Fremy's salt e. f. Problem Set 2. solutions O O 2 b. Make compound 2 starting from alcohols or hydrocarbons with 4 carbons or fewer O OH HO + H + O OH + heat CrO 3 /H + OH c. Make compounds 3 and 4 starting with compound containing 4 carbons or fewer ( 3 and 4 are unrelated). Watch out for stereochemistry! HO Cl Cl 3 EtO 2 C CO 2 Et CHO OHC 4 Cl Cl O Cl Cl Cl Cl + ! mCPBA Na + NaNH 2 CO 2 Et EtO 2 C O 3 /(CH 3 ) 2 S CO 2 Et EtO 2 C ! + CO 2 H HO 2 C HO + H +...
View Full Document

This homework help was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

Page1 / 3

Chem 317 - Set 2 extra problem Solutions - Need a different...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online