hyrdroboration and Diels-Alder reaction Flashcards

1
Q

what is hydroboration-oxidation

A

two step process resulting in anti-markovnikov addition of water across a double bond
Alkenes react with BH3

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2
Q

what is the regioselectivity of the addition of borane

A

boron will add to the least hindered end of the alkene

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3
Q

what is the mechanism of borane addition

A

concerted process bond formation isn’t simultaneous C-B bond forms before C-H partial positive formed on more substituted C .

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4
Q

what is the selectivity of hydroboration

A

syn addition BH2 and H in same direction

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5
Q

what are the uses of organoboron species

A

useful reagents for modern syntheses, alkyl boranes with alkaline H2O2 produces alcohols

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6
Q

what is the mechanism for the oxygen step of hydroboration-oxidation

A

LP from HOO- attacks empty P orbital on BR3 forming -BR3OOH, R group bonded to B migrates onto O and loss of OH group.
This repeats for the other 2 R groups leaving B(OR)3
B(OR3) undergoes hydrolysis forming B(OH)3 + 3ROH

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7
Q

what makes hydroboration-oxidation anti markovnikov

A

H bond to more stabilised position

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8
Q

whats is the Diels-Alder reaction

A

the reaction of an electron-deficient alkene with a conjugated diene giving cyclohexene

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9
Q

what conformation does the diene need to adopt for Diels-Alder

A

S-Cid (synperiplanar) to react so both new C-C bonds formed on same side dienophile

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