25eBookPrintReferences10 attempts leftAlkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonylcompounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which givesaldehydes from terminal alkynes.R-C=CH1. R'₂BH2. H₂O2, NaOHConversion of an Enol to a KetoneTHE OVERALL REACTION:HRCHEnolHHydronium ionOHR'The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw thestructure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "drawstructure" button to launch the drawing utility.+RCH:EnolCheck my workRR'BR 2AlkenylboraneOHHHTHE MECHANISM:Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbondouble bond.H₂O2Ketone(aldehyde if R' = H)H`'R'HWaterR1:O:+ RCH-+ÖHHR'HConjugate acidof ketone THE MECHANISM:Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbondouble bond.HBOHHHydronium ionRCH₂R'Conjugate acidof ketone1-Hexynedraw structure...+RCH=SÖHEnolStep 2: The conjugate acid of the ketone transfers a proton from oxygen to a watermolecule, yielding a ketone.¹H-H+ :0:R'HWaterH:O: +RCH-HWater1. R'₂BH2. H₂O₂, NaOHRCH₂KetoneR'R'HConjugate acidof ketone+ÖH+HexanalHH-O:HHydroniumionH

10 attempts left R-C=CH Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives aldehydes from terminal alkynes. Check my work 1. R₂BH 2. H₂0₂, NaOH R H H H₂O2 R H BR¹2 Alkenylborane The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw structure" button to launch the drawing utility.

10 attempts left R-C=CH Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives aldehydes from terminal alkynes. Check my work 1. R₂BH 2. H₂0₂, NaOH R H H H₂O2 R H BR¹2 Alkenylborane The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw structure" button to launch the drawing utility.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.12P

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