Ochem Rxns Ch
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65 Terms
What reagents?
HCl, HBr, or HI
Regiochemistry?
Carbocation rearrangements
Type of Reaction?
Sn1
What types of reactants to use this on?
tertiary and secondary alcohols
Product?
Product?
What reagents?
HBr or HI
What type of reaction?
Sn2
What type of reactants does this work best on?
primary alcohols
Product?
What type of Reaction?
Sn2
This reactions maintains or inverts stereochemistry?
Inverts
What type of reactants?
Primary and secondary alcohols ONLY
Product?
What reagents?
TsCl (or MsCl ot TfCl), Pyridine
NaNu
What type of reaction?
Sn2
Does this reaction maintain or invert stereochemistry?
Invert
What reagents?
HBr or HI
What product?
What type of reaction?
Sn1
Where will R’-X form?
Side that is more substituted
What reagents?
HBr or HI
What type of reactions is this?
Sn2
Where with R’-X form?
less substituted side
What reagents?
HCl, ROH
Where will the nucleophile add?
To the more substituted side
What type of reaction?
Sn1
What reagents?
RONa, ROH
Where will the nucleophile add?
less substituted side
What type of reaction?
Sn2
What are the reagents?
H2SO4, heat or POCl3, pyridine, 0 degrees celsius
Regioselectivity?
Carbocation rearrangements possible
What type of reaction?
E1 rxn
What type of reactants work best?
secondary and tertiary alcohols
Any regioselectivity?
Always forms Zaitsev product
What type of reaction
E2
What type of reactants work best?
secondary and tertiary alcohols
What reagents?
H2Cro4 (strong oxidizer)
Product?
Carboxylic Acid
What type of reactant works with this?
Primary alcohols
What reagents?
PCC, CH2Cl2 or NaOCl, CH3COOH (mild oxidizer)
What type of reactant works with this reaction?
Primary Alcohol
What reagents?
H2CrO4 or PCC, CH2Cl2 or NaOCl, CH3COOH (strong or mild oxidizer)
What type of reactants work?
secondary alcohols
What reagents?
OsO4
H2O2, H2O
What stereoselectivity is there?
Syn Addition
What is the product called?
cis diol
What reagents?
R2CuLi
HCl
Does this reaction invert or maintain stereochemistry?
Maintain it
What reactants work with this reaction?
aryl and vinyl halides
What reagents? (Suzuki Rxn)
PdL2, NaOH
Does this reaction invert or maintain stereochemistry?
Maintain it
What type of mechanism does the Suzuki Reaction use?
Palladium-catalyzed cross-coupling
What reactants can be used with the Suzuki Reaction?
Vinyl or Aryl Halides
What reaction is this and what are the reagents?
Heck Reaction
PdL2, (CH3CH2)3N
What is the product of a Heck Reaction
Trans alkene
What type of mechanism does the Heck Reaction use?
Palladium-catalyzed cross-coupling with Z being any functional group or alkyl chain
What are the reactants?
Br2, hv (light)
What type of reaction?
Radical reaction
Where does the radical form?
Most stable position
What type of reaction?
Radical reaction
Where does the radical form?
benzylic position
What reagents?
NBS, Heat (delta) , peroxide
What type of reaction?
Radical reaction
Where does the radical form?
allylic position
Note 
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