Dihydroxylation of alkenes (1)

Organic chemistry: Alkene addition reactions. Addition of OsO4 (osmium tetroxide) to achieve syn dihydroxylation. Using epoxides to achieve anti dihydroxylation. A synthesis problem. The synthetic toolbox. When does steric hindrance block one face of a trigonal planar intermediate?

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(1) Addition of OsO4 (osmium tetroxide) to achieve syn dihydroxylation
(2) Continued
(3) Continued
(4) Using epoxides to achieve anti dihydroxylation
(5) Continued
(6) A synthesis problem
(7) The synthetic toolbox. When does steric hindrance block one face of a trigonal planar intermediate?

Category:

Education

Tags:

• organic
• chemistry
• alkene
• electrophilic
• addition
• osmium
• tetroxide
• epoxide
• syn
• anti
• dihydroxylation
• alcohol
• synthesis
• MCPBA

[sadlmatt]

H2O2 does not cleave the osmate ester its just simply water! H2O2 reoxidises osmium oxide back to the tetroxide and so allows you to use it in sub-stoichiometric because A) its very expensive and more importantly B) its a very toxic volatile solid that will turn your eyes black.

[omaghphil]

i would appreciate the full mechanism here, some courses do require knowing these steps. I do believe there are 3 different ways though :/

[TooKute4U727]

for orgo 1, you do not need to know the mechanism for OsO4, just need to know about the reaction and the products. So what this guy did is even better than the university's requirements. Keep on with the good work !!!

[rahkel09]

@walkonthewildside101 agreed!!!!

[walkonthewildside101]

Thank you so much!!! I've been looking everywhere for this. My teacher just EXPECTED us to know it. You explained it very simply, which is just what I needed because now I'm off to take my test!! Thanks!!

[VPR2000]

@guzzbar I wasn't f'king complaining. I was just pointing shit out! And I'm pretty sure other users would want to see an entire mechanism since it's hard to find elsewhere on the internet!

[guzzbar]

@VPR2000

quit your bitchin, if you dont like it use all the other resources on the internet for organic chemistry.....which adds up to ZERO

this guy is a champion

he has covered a university course, and a course for the mcat

all for a pay what you like basis.....and u have the nerve to complain?

[guzzbar]

poorly explained?? if i could send you a SLAP through the internet i would...

[VPR2000]

You're missing lone pairs on the intermediate. -0.5 points, lol. No entire mechanism for a 10 minute video?

[valdezmiguel2]

by a robot/guy speaking through a fan.