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28 Cards in this Set
- Front
- Back
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SN2 Replacement of nucleophile (1º/2º alcohol)
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Tosyl Chloride / pyridine
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Ether synthesis (1º alcohol)
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X-R / DMSO (or other aprotic solvent)
also works to create cyclic ether if OH and halide are on the same compound, i.e. XCH2(CH2)nCH2OH |
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Ether synthesis from two alcohols
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Strong acid i.e. H2SO4, heat
works best with two identical alcohols as starting reagents to create symmetrical ether |
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1º Ether cleavage
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H-X
creation of alcohol and halide ; also works with other nucleophilic acids |
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2º/3º Ether cleavage
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H3O+ / H2SO4
may result in multiple products because of carbocation rearrangement |
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Protection of OH groups
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(1) HOBut / H2SO4 and ether
(2) reaction of desired reagent (i.e. Grignard with a molecule including both a halide and an OH) (3) Cleavage of ether with H3O+ |
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Epoxide cleavage in basic conditions
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H3O+ / H2O
anti addition of OH group and :Nuc |
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Epoxide cleavage in acidic conditions
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OH- or OCH3- / H2SO4
anti addition of OH group and :Nuc |
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Grignard reactions with epoxides
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R-MgBr
attacks less substituted carbon, resulting in anti addition of OH group and R group after H3O+ workup |
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Addition of halide to alkene (simple)
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H-X / CH2Cl2
carbocation rearrangements |
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Addition of OH to alkene
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H2O / HClO4 or H2SO4
carbocation rearrangements |
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Addition of halide to alkene (preferred method)
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HBr / R-O-O-R
hv -->anti-Markovnikov addition of Br |
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Dihalogenation of alkenes
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X2 / CH2Cl2
stereospecific |
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Addition of halide and OH to alkenes
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X2 / H20
X-onium ion is formed, then H2O attacks most substituted carbon with partial+ charge. Anti addition. Also works with other nucleophiles, i.e. OCH3 |
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Alkene --> alcohol (Markovnikov)
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(1) Hg(OAc)2 / H2O or THF
(2) NaBH4 / NaOH workup puts OH on most substituted carbon |
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Alkene --> alcohol (anti-Markovnikov)
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(1) "BH3" / THF
(2) OH- / H2O puts OH on least substituted carbon |
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Alkene --> epoxide
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(1) X2 / H20
(2) OH- / H2O (not preferred) OR MCPBA / CH2Cl2 (metachloroperoxybenzoic acid) |
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Cyclopropanation of alkenes
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CH2I2 / Zn
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Cyclopropanation of alkenes with halides attached!
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HCCl3 OR HCBr3 / KOBut OR HOBut
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Anti addition of two hydroxyls to an alkene
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(1) MCPBA / CH2Cl2 --> epoxide
(2) NaOH / H2O (3) H3O+ / H2O workup |
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Syn addition of two hydroxyls to an alkene
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(1) OsO4 / CH2Cl2
(2) H2O2 OR (1) KMnO4 (2) NaOH / H2O |
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Alkene --> two carbonyl groups
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called "Ozonolysis"
(1) O3 (2) Zn |
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Syn addition of H or D to alkene (alkene -->alkane)
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H2 or D2 / PtO2
OR D2 / ClRh(PPh3)3 |
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1º halide --> alcohol
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(1) CH3CO2- Na+ / H2O
(2) OH- / H2O using 3º halides will typically result in E2 |
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Ketone OR Aldehyde --> alcohol
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(1) NaBH4 OR LiAlH4 / Ether
(2) H3O+ / H2O workup --> secondary alcohol |
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1º Alcohol --> Acid
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H2CrO4 / H2SO4
over-oxidation |
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1º Alcohol --> Aldehyde
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PCC (pyridium chlorochromate)
Oxidation |
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2º or 3º acid --> ketone
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H2CrO4 / H2SO4
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