1. Show the reaction, along with the transition state (‡), between 2-methyl-2-pentene and BH3 in THF....

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Chemistry

1. Show the reaction, along with the transition state (‡),between 2-methyl-2-pentene and BH3 in THF. Then, show thesubsequent reaction of the organoborane intermediate with H2O2 andOH-1. Explain why hydroboration is non-Markovnikov and forms a 2oalcohol. Refer to hydroboration in the chapter notes, the handoutfor example 8.2, and figure 8.4 in text. (2 pts)

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4.2 Ratings (902 Votes)
Insteadof proceeding in multiple steps as do reactions in the carbocationand 3 membered ring pathway the hydroboration reaction occursall at once That is the mechanism is concertedThose dashed lines represent partial bonds The new bonds tocarbon are forming at the same time as the CC bond is breakingThe result is that the stereochemistry is synWhy does the hydrogen end up bound to the mostsubstituted carbon rather than the least Think of the transitionstate for this reaction As the CC bond breaks any partialpositive charge from the alkene carbons would be most favorablysituated on the carbon best able to accept it the mostsubstituted carbon    See Answer
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