-
Making Cyclopropanes
C=C --?,?-->
C=C --?--> 
- ? CH2N2, light
- ? CH2I2, Zn(Cu)
? CHX3, NaOH(aq)
-
Making Epoxides
C=C --?--> 
- MCPBA, CH2Cl2
- peroxyacid, nonpolar solvent
-
Making Glycols (1,2 Diols)
C=C --?,?--> 
- ? HCO2H, H3O+
- peroxyacid, H3O+
- ? OsO4, H2O2 or KMnO4, OH-
-
Making Alkenes
 --?,?--> C=C
- 1. ? KOH (alc)
- E2 anti elimination
- 2. ? H2SO4
- E1 rearrangement possible, major and minor products
-
Making Alkynes (vicinal dihalide)
 --?--> ? --?--> R-C(triple bond)C-R'
- ? KOH (alc)
- ?
 - ? NaNH2
-
-
 +Br2 --?--> ?
- light
-
--?--> 
NaOCH3 & CH3OH
-
-
For use in Friedel-Crafts alkylations
protonate alkene
- HF
- F- can be used to draw off proton at the end too
-
For use in Friedel-Crafts alkylations
OH with ___
- + Lewis acids like BF3
- BF3 isn't regenerated
-
Make alkenes with alcohol, have to have a __ oposite
React with ____
will have major and minor products
-
Hydrate alkenes
C=C + ___
__markonikov
__rearrangement
-
Oxymercuration - demercuration
React with _____
__markovnikov
__rearrangement
__addition
-
Hydroboration-oxidation
react with ___
__markovnikov
__rearrangement
__addition
- BH3 THF, H2O2 OH-
- anti
- no
- syn
-
Cis C=C, __ stays on them but __ gets replaced with Br
when you react with ___
gives you a ___ mixture optically ____
- H
- CH3
- Br2, CCl4
- racemic
- inactive
-
Trans C=C, __ stays on them but CH3 replaced.
react with ___
gives ___ mixture
optically ___
-
Williamson synthesis
R-? ---?---> R-O-R'
R = ? or ?
-
Alkoxymercuration-demercuration
C=C --?--R-OH--?--> ?
- Hg(OAc)2, NaBH4
- C-C-C
- .....|
- ....OR
-
Making alkynes
new C(triple bond)C between vicinal dihalide
dehydrohalogenation
start with
 R-C(triplebond)C-R'
KOH(alc), NaNH2
-
Making alkynes
new bond between geminal dihalide
- KOH (alc), NaNH2
- R-C(triple bond)C-R'
-
New alkyne from smaller alkynes
new C-C bond
like williamson synthesis
acetylide ions:
R-X _ R'-C(triplebond)C- --> ?
- R-C(triplebond)C-R'
- nucleophilic aliphatic substitution
-
New alkyne from smaller ones
if aldehyde:
Ketone
- R'-C(triplebond)C-
- H3O+
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