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Organic Comp 1 Final Spr04


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mCBA ,(CHCl3)
epoxide from alkene, syn addition (racemic)
KOH, alc
primary double bond from primary halide or alkene from halide;
KOH always elimination
Cl2, CCl4
dicloro from double bond, anti
DMF solvent (aprotic)
SN2 adds to smaller molecules together
dry ether
OMgBr from carbonyl + MgBr
ether(in middle)from primary halogen
HCl, ZnCl2
primary Cl from OH; complete substitution
reduced to alkene and added
CH3CH2(w/o the I) to less substituted C
C=O bonds
O is more electronegative and is electron rich; carbonyl os strongly polorized;addition follows nucleophile to C;electrophile to O
How acidity increases
weaker acid on left
No reaction b/c rxn goes to left
Retrosynthesis (working backwards) Steps
Look for ways to break up molecule
1.Identify functional group in the compound to be sythysized
2.How is that functional group formed?
3.choose best method the one with the best yield.
4.write the chemical equation with the specific compounds that under go the reaction to form the desired product.
5.repeat until the reactants are the permitted starting materials.
3 features of SN rxns at sp3
1)sp3 hybrid carbon atom
2)leaving group
Common leaving groups
Halogen atoms;ArSO3(arene sulfonates); NR3+ (amonium ions);SR2(alkyl sulfonium ions
common nucleophiles
1)mostly neg charge (OH-,CN-
2)neutral (I,NH3,H20,and alcohols)
all have at least on pair of electrons to form bond with sp3 C atom
nature of leaving group
decreasing base strength generally increase the rate, the less basic the leaving group the more easily it leaves
SN1 reactions usually
will form a carbocation; is only option with tertiary;for secondaary compounds, when leaving group is good;nucleophile is weak;solvent is polar
SN2 rxns
nucleophile is very good;polar aprotic solvent; support backside approach
OAc replaces halogen from back side;SN2 b/c weak base
2)H2O, Zn
cleaves double bond alkene to form carbonyl; ?forms ide & ozonide?
TsCl or AcCl, pyr
Ts or Ac replaces H of alcohol (O remains)

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