elimination Flashcards
elim vs sn
-both have leaving groups but sn replaces it w nu
-often compete
-emilination= FORM ALKENE
formation of alkene
caused by the loss of the beta hydrogen
two main mechanism
e1 and e2
e2
bimolecular
-involves the substrate and the base in one single step
where will the double bond form?
-all about regiochemistry
-how many groups on each double bond
zatziev product
-more substituted alkene
-most times is the major product UNLESS IT IS A BBB
-ALL ABOUT WHERE THE RXN TAKES PLACE
BBB
chose hofman product/ less sub
-tbuok and lda
product of e2 reaction
-can be controlled based on which base you use cause one leads to more sub and one leads to less sub product
identical beta h positions
-regiochemistry is not an issue, no matter where rxn happens same outcome
-stereochem important
-if cis and trans are product, trans is favored
steroselective e2
-cis and trans are the product and they both have the same regiochemistry
-trans is favored
-results in a mixture
stereospecific e2
-antiperiplanar
-results in one alkene
-draw newman projection to make sure they are in a line
-does not produce stereoisomers
one proton
-is stereospecific, will only get one alkene
-draw newman projection and make sure it is aniperiplanar
newman projection
-use to determine the stereoisomer product of e2 reaction
e1
two steps
-leaving group leaves
-lose of the proton
-the base is not involved in step one therefore unimolecular all about the substrate
-compete with sn1 and product is a mixture
e1 alkyl halids
prefer secondary and tertiary
-primary will not go e1
sn2
will not be tertiary (too bulky)
-but e2 can be tertiarty bc there is not attack
e2 alkyl halide
tertiary is fastest
oh
bad leaving group
e1 of an alcohol
there will be a protonation step first because oh is a bad leaving group
-strong acid used to protonate
-product is h2o+ which is an excellent leaving group
e1 and e2
prefer zatsev product as the major product
e1 product
CAN NOT BE CONTROLLED BY USING A BBB
regiochemical outcome
where the alkene bond will go which will lead to zaitzev or hoffman
are e1 reactions stereospecific
NO
-do not need antiperiplanarity to run reaction
-they are stereoselective when cis and trans happen
stereospecific
changing reactant changes product
-only e2