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Chem 315 Reactions Through Topic 11

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Chem 315 Reactions Through Topic 11 Web pages Beauchamp 1 Propose synthetic reactions for the indicated target structures from the given starting materials. Show the starting material (methane, ethane and propane), a reaction arrow with the reagent and a product for each synthetic step of your synthesis. If a compound has been prepared earlier you do not need to remake it (just refer to the part where you made it). Common organic reagents may be used as needed. Additional “carbon” compounds available include bromobenzene, cyclohexane, carbon dioxide and sodium cyanide. 1. Given starting material = methane,(CH4) Target molecules (the part from methane has the “C” written out). 6 1 2 3 4 5 N 7 89 O H C NH H C SH C O H3C Br H3C OH 3 2 3 CH H C H3C 3 CH 3 H3C 3 methane + Br /hνa. 1 + ester (S 2) 2 N 1. 1 + O 2 + HBr (2 ways) b. ester + NaOH a. propyne + NaNR2 (2 ways) 2 + PBr3 + 1 + NaCN (SN2) 31 + H3O , H2O N b. bromomethane 2 + SOBr2 RO + RBr (S 2) a. 31+HgX /H O a. 40 + NaNR2 N 2 + a. TsCl/py 2 2 1 + NaSH (SN2) b. NaBH b. bromomethane b. NaBr 4 (SN2) O a. 13 + NaBH4 2. NaOH b. WK 10 11 O 12 O 13 O 14 O 15 O O CH3 CH3 C CH3 C C C H O H O H O H O (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) RO + RBr (SN2) RCO + RBr RO + RBr (SN2) RCO2 + RBr RCO2 + RBr RCO2 + RBr 2 (S 2) (S 2) (S 2) ROH + RBr (S 1) N (SN2) N N N RCOCl + ROH RCOCl + ROH RCOCl + ROH RCOCl + ROH (acyl substitution) (acyl substitution) (acyl substitution) (acyl substitution) OH OH 20 OH 21 OH O 23 16 O 17 O 18 19 22 C C H3C OH H3C H3C OH H3C CH3 H H H OH H3C H3C a. 1 + Mg (or Li) 2 + CrO /py 2 + CrO /H O a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) 3 3 2 a. 1 + Mg (or Li) b. CO (PCC) (Jones) b. methanal b. ethanal b. propanal b. propanone 2 b. alkyl methanoate c. WK c. WK c. WK c. WK c. WK c. WK 24 OH 25OH 26 27 28 O 29 O OH OH H3C H C H3C 3 H3C H3C H3C CH3 CH3 acid chloride + cuprate a. 1 + Mg (or Li) acid chloride + cuprate a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) b.3C epoxide b. propanenitrile b. alkyl propanoate b. 2C epoxide b. ethanenitrile b. alkyl ethanoate c. WK c. WK propanoic acid + c. WK c. WK ethanoic acid + 2 eqs methyl lithium 2 eqs methyl lithium O 36 O 30 31 32 33 34 35 CH3 CH3 H3C H3C H3C H3C (2 ways) (2 ways) (2 ways) (2 ways) 1. ketone + LDA cuprate + RBr cuprate + RBr cuprate + RBr CH3 cuprate + RBr (2 ways) 2. RBr (compound 1) cuprate + enone cuprate + RBr (conjugate addition) a. enamine + 1 b. H2O (hydrolysis) Z:\classes\315\315 Handouts\temp for web.doc Web pages Beauchamp 2 2. Given starting material = ethane,(CH3CH3) 8 1 2 3 4 5 6 7 9 N O O NH C Br OH 2 SH a. 1 + ester (S 2) 1 + O ethane + Br /hν N 1. (2 ways) (2 ways) 2 b. ester + NaOH a. 40 + NaNR a. propyne + NaNR2 2 + HBr + 2 31 + H3O , H2O N 1 + NaSH (SN2) 1 + NaCN (SN2) b. bromoethane 2 + PBr3 b. bromoethane RO + RBr (S 2) a. 31+HgX /H O N 2 + SOBr2 2 2 2 + a. TsCl/py b. NaBH4 (SN2) O b. NaBr a. 13 + NaBH4 2. NaOH b. WK 11 O 13 O 14 O 15 O 10 12 O O R O O O O (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) RO + RBr (SN2) RO + RBr (SN2) RCO + RBr RCO + RBr RCO2 + RBr RCO2 + RBr 2 2 (S 2) (S 2) (S 2) ROH + RBr (S 1) (SN2) N N N N RCOCl + ROH RCOCl + ROH RCOCl + ROH RCOCl + ROH (acyl substitution) (acyl substitution) (acyl substitution) (acyl substitution) 16 O O O OH O 17 18 19 20 OH 21 OH 22 23 OH O H OH OH (2 ways) a. 40 + R2BH 2 + CrO3/H2O (Jones) a. 1 + Mg (or Li) RCO + RBr b. H2O2 / HO a. 1 + Mg (or Li) 2 a. 1 + Mg (or Li) a. 1 + Mg (or Li) b. CO2 a. CH3Br/Mg b. methanal (SN2) a. 1 + Mg (or Li) b. propanal b. propanone c. WK + b. CO2 c. WK RCOCl + ROH 40 + H3O /H2O b. ethanal c. WK c. WK (acyl substitution) c. WK c. WK 5 + H2SO4/H2O 2 + CrO3/py (PCC) ethanenitrile + H2SO4/H2O/∆ OH OH 26 OH 28 24 25 27 29 O OH OH acid chloride + cuprate a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) b.3C epoxide b. ethanenitrile b. alkyl methanoate b. alkyl ethanoate b. alkyl propanoate b. 2C epoxide c. WK c. WK ethanoic acid + c. WK c. WK c. WK 2 eqs ethyl lithium O O 30 O 31 32 33 34 35 36 37 acid chloride + cuprate (2 ways) (2 ways) a. 1 + Mg (or Li) (2 ways) (2 ways) (2 ways) 1. ketone + LDA b. propanenitrile cuprate + RBr cuprate + RBr cuprate + enone ethanoic acid + cuprate + RBr cuprate + RBr cuprate + RBr (conjugate addition) 2. RBr (compound 1) 2 eqs propyl lithium a. enamine + 1 b. H2O (hydrolysis) 38 39 40 41 42 43 O Br Br HO Br OH OH 1 + K+ t-butoxide 38 + mCPBA 38 + OsO Br a. 39 + NaNR2 4 2 Br2 / H2O (or KMnO ) 2 + H2SO4/∆ b. WK 41 + NaOH 4 Wittig = methanal + ylid Z:\classes\315\315 Handouts\temp for web.doc Web pages Beauchamp 3 3. Given starting material = propane,(CH3CH2CH3) a. 1 2 3 5 8 9 10 4 N O C O O OH Br NH2 SH a. 1 + ester (S 2) N 1 + O propane + Br2/hν b. ester + NaOH 1. 2 + HBr 31 + H O+, H O (2 ways) (2 ways) (2 ways) 2 + PBr 3 2 N 1 + NaCN (SN2) 3 a. 31+HgX /H O 2 + SOBr 2 2 RO + RBr (S 2) RO + RBr (SN2) 2 1 + NaSH (SN2) RO + RBr (SN2) N b. NaBH4 2 + a. TsCl/py (SN2) O b. NaBr a. 13 + NaBH4 ROH + RBr (S 1) ROH + RBr (SN1) 2. NaOH ROH + RBr (SN1) N b. WK 11 O O 14 15 OH OH 12 13 16 OH 17 O OH R O (2 ways) (lots of ways) ROH + RBr (S 1) RCO + RBr 2 + CrO3/H2O N 2 a. 1 + Mg (or Li) (Jones) a. 1 + Mg (or Li) (SN2) b. methanal a. 1 + Mg (or Li) a. 1 + Mg (or Li) RCOCl + ROH 2 + CrO /py b. ethanal b. propanal b. propanone 3 c. WK c. WK (acyl substitution) (PCC) c. WK c. WK + 33 + H3O /H2O ...and more O O 18 19 OH 20 21 22 23 24 O OH Li OH OH Cu a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) a. 1 + Mg (or Li) b.3C epoxide cuprate acid chloride + cuprate acid chloride + cuprate b. CO2 b. alkyl methanoate b. 2C epoxide c. WK a. 1 + Mg (or Li) a. 1 + Mg (or Li) c. WK c. WK c. WK 2RLi + CuBr b. ethanenitrile b. propanenitrile ethanoic acid + ethanoic acid + 5 + H2SO4/H2O 2 eqs propyl lithium 2 eqs propyl lithium 25 26 29 O O 27 28 30 31 1. ketone + LDA (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) 2. RBr (compound 1) cuprate + RBr cuprate + RBr cuprate + RBr cuprate + RBr cuprate + RBr cuprate + enone (conjugate addition) a. enamine + 1 b. H2O (hydrolysis) 33 34 37 32 35 36 O Br Br HO OH Br OH a. 32 + NaNR 31 + mCPBA + 2 31 + Br2/H2O 31 + H2O2 / HO 1 + K t-butoxide 31 + Br2 b. WK 34 + NaOH 38 O 41 42 all from 39 O 40 43 H (lots of ways) 1. R2BH a. NaNR2 39 + Na / NH3 39 + Pd / H2 39 + Pd / H2 b. H2O2 / HO 2 + CrO3/H2O b. CH3-Br quinoline (Jones) 2 + CrO3/py (PCC) + 33 + H3O /H2O ...and more Z:\classes\315\315 Handouts\temp for web.doc Web pages Beauchamp 4 b. 4 1 2 3 5 N 6 7 C SH NH2 Br OH 1. O 2 + HBr 1 + NaOH (SN2) 1 + NaCN (S 2) 2 + PBr 1 + NaSH (SN2) N 1 + NaCCH (SN2) 1 + NaCCCH3 (SN2) 3 31 + a. BH3 N 2 + SOBr 2 b. H2O2, HO 2 + a. TsCl/py (S 2) b. NaBr N O 2. NaOH 11 O 8 9 10 12 O O O O R O (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) RO + RBr RO + RBr RO + RBr RO + RBr RCO2 + RBr (both S 2) (both S 2) (both SN2) N N (both SN2) (SN2) RCOCl + ROH (acyl substitution) 13 O 14 O 15 O 16 O 17 O 18 O O O O O H OH (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) (2 ways) 2 + CrO3/py RCO + RBr RCO2 + RBr RCO2 + RBr RCO2 + RBr 2 (PCC) 2 + CrO3/H2O (S 2) (SN2) (SN2) (SN2) N 33 + a.
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