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nike_victoria
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OrganicChemistry

Post by nike_victoria »

Draw the mechanism of the reaction of (R)-2-bromooctane with NaCN in HMPA solvent.
Elle Spark
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Re: OrganicChemistry

Post by Elle Spark »

SN2 conditions:
good nucleophile, poor base
good leaving group
2o
alkyl halide so not too much
steric hindrance for backside
attack.
E1 conditions:
weak base, poor nucleophile
good leaving group
polar aprotic solvent
2o
carbocation
will make most stable alkene
E2 & SN2 conditions favored. E2 will be major product.
good nucleophile and strong base
good leaving group, can make products without a carbocation
steric hindrance in SN2 rxn will make it.
SN2 conditions:
good nucleophile, poor base
good leaving group
2o
alkyl halide so not too much
steric hindrance for backside
attack. polar protic solvent helps
solvate leaving group
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