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24 Cards in this Set

  • Front
  • Back
hydrogenation of alkenes
alkene + H2(metal catalyst/ pt, pd,RH, ni----->
alkane
no Regiochemistry since adding two of same(h's)
Stereochemistry: SYN addition( will get 2 enantiomers)
but is also stereoselective by adding to less crowded face of double bond( when this happens you'll oly get one product)
electrophilic addition of hydrogen halides to alkenes :
alkene + HBr/ HCl ----->
solvents: ChCl3, acetic acid,
alkyl halide
Regiochemistry : Markovnikovs ( halogen on most subs C) watch for poss rearrangements with hydride or methyl shifts, protonatiion occurs in direction that forms most stable carbocation
free radical addition of HBr to alkenes
only used with hbr!!!
alkene + Hbr with peroxides(ROOR)----> or
alkene + Hbr with light with or with out peroxides--->
anti markovnikov primary alkyl halide

Regiochemistry is anti markovnikov: br added to less substituted carbon
with addition mechanisms if you create a just 1 new stereo center you will get two products ( pair of enantiomers regardless if syn or anti addition)
know
hydration of alkenes using an acid catalyst
alkene to produce an alcohol ( this reaction is the opposite of our dehydration of alcohol beta elimination reaction
alkene + H3o+\ H20------> or
alkene + H2SO4/ H20---->
alcohol
Regiochemistry : markovnikov

poss rearrangements with methyl or hydride shifts
if we want to form the alkene starting from an alcohol we would use concentrated acid ( elim rxn)
if we start with alkene and want to from alcohol we need a diluted acid so that's why we have acid + h20
know
hyrdoboration oxidation of alkenes :
alkene + BH3, THF/ H202, NaOh----> or
alkene + B2H6(diglyme)/H202,OH- ---->
forms an anti markovnikov alcohol
regiochem : anti mark oh grp ends up on least subst c
stereochemistry: syn addition
synthesis techniques: substitution lets us
change grps
elimination reactions lets us form
alkenes
addition reaction lets us add two grps across double bond
can turn into alcohols or alkyl halides
if we have something that's changes positions from one car on to other easiest way is to eliminate then re add
1. for alkyl halides for elimination for zaitsevs product( most subs double bond use.....
2. for Hoffman product( least subt double bond) use...
1. NaOet
2. t-buOK
for alcohols that you need to move to diff position of carbon need to eliminate first then add as well
if need to eliminate using Hoffman product( double bond forms to give least substituted double bond first change oh into good leaving group
1. TsCl, pyridine( changes alcohol into Ots (toslate) which is better LG
2. then use strong steric ally hindered base to eliminate to Hoffman product( t-buOK)
3. then use addition to give anti mark or mark of alcohol
to eliminate alcohols to zaitsevs product use
h2so4, heat
when just start with alkane and need to form alkene and there are no functional grps on it only thing to do is radically brominate
this will add br on most substituted carbon then from there you can eliminate to form double bond
use NBS, light
addition of halogens to alkenes
alkenes + br2---->
(limited to br2 and cl2)
forms a vicinal dihalide: two adjacent carbons with a halide on each...br added to pop sides of double bond which will form enantiomers
Regiochemistry : irrelevant due to same atoms
stereochemistry : Anti addition
bromonium ion formed in first step, then attacked back side due to bridged ion which explains anti addition
halohydrin formation
alkene + br2 and H2o--->
alkene converted to vicinal halohydrin: br and oh grps
Regiochemistry OH on most subst C
stereochemistry: Anti only product!!!
carboxylic acid
RCdouble bond O OH
Cooh
formula :RCO2H
peroxy acid
RC double bond OOh
COOOH
resembles carboxylic acids but has one more O
formula :RCO3H
Epoxidation of alkenes
alkene + peroxyacid( RCO3H)
solvents used: HClO4
HClO3 HClO2, HClO
forms epoxide3membered ring that contains O (and a carboxylic acid (RCO2H)
stereoselectiveNess : syn addition
Ozonolysis
alkene + O3/ CH3)2S
or O3/ Zn, H2o
will completely cleave double bond forming either 2 aldehydes, 2 ketones, or one of each
aldehyde
RC double bond oH

or just think of it as c double bond oh only attached to one other C
ketone
c double bond O attached to 2 C
this will be major product over aldehyde
for ozonolysis for each C double bond C we simply erase that bond and put 2 C double bond O in its place
trick
when you only show one product means symmetric on no sides of double bond if going from reverse in ozonolysis
know