EPOXIDE RING OPENINGS: ACIDIC
WHICH CARBON DOES IT ATTACK?
MORE SUBSTITUTED
ARE THESE REACTIONS MORE BASIC OR MORE NUCLEOPHILIC?
NUCLEOPHILIC
WHAT IS THE MAJOR PRODUCT OF E2?
NON ZEITSEV
WHAT SOLVENT IS BEST FOR SN1 AND SN2 REACTIONS?
SN1= POLAR PROTIC
SN2= POLAR APROTIC
OXYMERCURATION GIVES YOU WHICH PRODUCT?
MARKOVNIKOV ALCOHOL
ON WHICH CARBON IS THE STEREOCHEMISTRY EFFECTED?
MORE SUBSTITUTED CARBON
ON WHICH CARBON IS THE STEREOCHEMISTRY EFFECTED?
LESS SUBSTITUTED CARBON
WHAT ARE THE STEREOCHEM REQUIREMENTS FOR E2?
ANTI-COPLANAR
WHICH PATHWAY CAN TERTIARY, SECONDARY AND PRIMARY SUBSTRATES DO?
TERTIARY= SN1 FOR WEAK NUC
SECONDARY= SN2 FOR NON BULKY/STRONG NUC, SN1 FOR WEAK NUC
PRIMARY= SN2 WITH STRONG NUC
HYDROBORATION GIVES YOU WHAT TYPE OF PRODUCT?
ANTI-MARKOVNIKOV ALCOHOL
DOES THE OXYGEN OF THE EPOXIDE HAVE A POSITIVE OR NEGATIVE FORMAL CHARGE DURING THE INTERMEDIATE STAGE?
POSITIVE
DOES THE OXYGEN OF THE EPOXIDE HAVE A POSITIVE OR NEGATIVE FORMAL CHARGE DURING THE INTERMEDIATE STAGE?
NEGATIVE
WHICH PATHWAY IS CAPABLE OF REARRANGEMENTS?
E1
STEREOCHEMISTRY OF SN2?
INVERSION OF STEREOCHEM (S AND R)
MIXING AN EPOXIDE RING WITH H2SO4/H20 CREATES WHAT TYPE OF PRODUCT?
ANTI/TRANS DIOLS
DRAW A MECHANISM FOR THIS REACTION. (USING HBr)
O FROM THE EPOXIDE ATTACKS THE H, H IS MOVED TO THE Br. Br- ATTACKS THE MORE SUBSTITUTED CARBON, STEREOCHEM IS INVERTED ON THE MORE SUBSTITUTED CARBON.
DRAW A MECHANISM FOR THIS REACTION. (USING NaNH2)
NH2 ATTACKS THE LESS SUBSTITUTED CARBON, THE STEREOCHEM IS INVERTED AND THE NH2 IS ADDED TO THE LESS SUBSTITUTED CARBON, THE O FROM THE INTERMEDIATE ATTACKS THE H OF A WATER, END PRODUCT HAS AN OH AND AN NH2.
WHAT IS THE MAJOR PRODUCT OF E1?
ALWAYS GET ZAITSEV AS THE MAJOR PRODUCT
STEREOCHEM OF SN1?
RACEMIC MIXTURE, CARBOCATION REARRANGEMENTS AVAILABLE.
LIST SOME NON-BULKY / STILL STRONG NUCLEOPHILES.
OH- NH2- OCH3- SH- (ALL SN2)
WHY ARE EPOXIDES MORE REACTIVE THAN STANDARD ETHERS.
RING AND TORTIONAL STRAIN
WHAT PATHWAY IS THIS?
SN2
WHICH PATHWAY CAN TERTIARY, SECONDARY AND PRIMARY SUBSRATES DO?
TERTIARY= E2 WITH A STRONG NUC, E1 WITH A WEAK NUC
SECONDARY= E2 WITH A BULKY NUC, E1 WITH A WEAK NUC
PRIMARY= E2 (ONLY WITH TURTBUTOXIDE OR H-)
RATE OF SN2? RATE OF SN1?
SN2= DEPENDS ON CONCENTRATION OF BOTH THE SUBSTRATE AND THE NUCLEOPHILE
SN1= DEPENDS ONLY ON THE CONCENTRATION OF THE SUBSTRATE
MIXING AN ALKANE WITH OSO4/PYRIDINE CREATES?
SYN-DIOLS