Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of theantitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171)Possible bases to considerH-C=C-HAcetyleneStep 1Li :BaseTH-O: LiLithium hydroxide (LiOH)three stepsLithiumacetylideDraw the structure of lithium acetylide.Draw Your Solutiondi.Η Η Η Η| | | |H-C-C-C-C:IIHH HHButyllithium (BuLi)ORCEC-LiOHCH3-HCH3Lithium diisopropyl amide (LDA)OMeH3CHH₂Cmany stepsLiHOOHI(+)-Acutiphycin CH3CH₂"OH

Terminal alkynes are weakly acidic. They are Bronsted acids as they release protons upon reaction…

Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 e Li :Base H-O: Li Lithium hydroxide (LiOH) Lithium acetylide three steps Draw the structure of lithium acetylide. Draw Your Solution Η Η Η Η II II H-Ċ-Ċ-Ċ-c: IIII Η Η Η Η Butyllithium (Buli) OR -CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe O H3C H- H₂C e many steps HO OH (+)-Acutiphycin CH3 "OH CH3

Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. (Org. Lett. 2014, 16, 1168-1171) Possible bases to consider H-C=C-H Acetylene Step 1 e Li :Base H-O: Li Lithium hydroxide (LiOH) Lithium acetylide three steps Draw the structure of lithium acetylide. Draw Your Solution Η Η Η Η II II H-Ċ-Ċ-Ċ-c: IIII Η Η Η Η Butyllithium (Buli) OR -CEC- Li OH CH3 -H CH3 Lithium diisopropyl amide (LDA) OMe O H3C H- H₂C e many steps HO OH (+)-Acutiphycin CH3 "OH CH3

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 25MP: Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of...

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