hyrdroboration and Diels-Alder reaction Flashcards
what is hydroboration-oxidation
two step process resulting in anti-markovnikov addition of water across a double bond
Alkenes react with BH3
what is the regioselectivity of the addition of borane
boron will add to the least hindered end of the alkene
what is the mechanism of borane addition
concerted process bond formation isn’t simultaneous C-B bond forms before C-H partial positive formed on more substituted C .
what is the selectivity of hydroboration
syn addition BH2 and H in same direction
what are the uses of organoboron species
useful reagents for modern syntheses, alkyl boranes with alkaline H2O2 produces alcohols
what is the mechanism for the oxygen step of hydroboration-oxidation
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
what makes hydroboration-oxidation anti markovnikov
H bond to more stabilised position
whats is the Diels-Alder reaction
the reaction of an electron-deficient alkene with a conjugated diene giving cyclohexene
what conformation does the diene need to adopt for Diels-Alder
S-Cid (synperiplanar) to react so both new C-C bonds formed on same side dienophile