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DMSO In this problem, the stereochemistry is "retained"...if we use
SN1 chemistry, a mixture between R and S will be formed. We know
that SN2 chemistry flips the stereochemsitry (see above)...thus to
"retain" stereochemistry we must do TWO SN2 reactions back to back.
Adding tosyl to the alcohol makes it a good leaving group...eliminating the
need for strong acid (which could promote SN1 chemistry). We must use
a different nucleophile in the first SN2 reaction because there would be
no selectivity in the second reaction if both the LG and Nu were Br. 2 Sessler CH310N Homework Problem Set 2 Due Friday February 3rd, 2012 c. O H2CrO4
Br H2SO4 NaNH2 OH H2O The only way we know how to functionalize an alkane is to use
free radical halogenation. Strong base converts to the alkene,
which we know many way to covert to the alcohol. Finally, in
chapter 10 we learned about chromic acid oxidation...
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- Fall '12
- Organic chemistry, Aldehyde, Cr OH, Sessler