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45 Cards in this Set
- Front
- Back
Alkyne-> Aldehyde
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hydroboration, BH3/TH__H2O2/OH
enol -> aldehyde |
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Alkyne -> trans alkene
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Na(s) ___ NH3 (l) uses free electrons
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Alkyne -> alkane
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H2__Pd/C for alkane
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Alkyne -> cis alkene
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H2__Pd/C and LIndlar poison such as Pb(OAc)2
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Alkyne -> Alkyne
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strong base such as LDA/n butyl Li
and primary alkyle bromide. attacks with carbanion |
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Alkyne -> alkene with Br
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Br2 __ CH2Cl2 trans Br
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Ketone -> Alkyne
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PCl5 to geminal dicholoride with NaNH2 __NH3 to alkyne
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Alkene -> Alkyne
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Br2__CH2Cl2 to alkyl halide with LDA to alkyne. no stereochemistry
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Alcohol -> alkene
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H3O+ E1 elimination doesn't occur with primary alcohol
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1 Alcohol to Aldehyde
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Pyridinium chlorochromate__CH2Cl2
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2 or 3 alcohol to alkene
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E2 elimination with sulfonate elster as LG
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Alkene -> Alcohol
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Br2 forms more substituted alcohol.
may also form vicinal dibromide |
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Alkene -> Alcohol
(Anti-markovnikov) |
1. BH3/THF
2. H2O2/OH- gives less substituted alcohol |
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Epoxide ring opening
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epoxide + HBr__CH2Cl2.
Br attacks less substituted ring |
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Alkene -> alcohol
(markovnikov) |
oxymercuration
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Alkoxides
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Alcohol + NaH
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Epoxide -> Amine
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1. epoxide and NaN3
2. acid workup 3. H2.Pd/C |
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Halogen -> Amine
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1. alkyl halide + NaN3
2. acid workup 3. H2 Pd/C |
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1 Alcohol -> Aldehyde
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PCC__CH2Cl2
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Alcohol protection
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Benzyl ether. 1. NaH 2. BnBr
(whatever reaction you actually want to do) 3. H2__Pd/C |
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Alkyne -> Ketone/aldehyde
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1. H3O+
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C--C bond formation
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!. alkyl Li. Li__hexane with alklyl Br
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1 Alcohol -> Carboxylic acid
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1. KMnO4 2. HCl
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1 or 2 Alcohol -> aldehyde, ketone
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1. Na2CrO4__H2SO4/H3O+
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Alkene -> aldehyde, ketone
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O3__(CH3)2S
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glycol -> aldehyde/ketone
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HIO4__H2O
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Epoxide ring opening
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Li organocuprates__hexane.
not effective with complex epoxides |
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1 Alcohol -> carboxylic acid
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K2Cr2O7___aqueous H2SO4
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alkyl bromide -> C----C bond formation
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alkyl bromide + Mg___THF or ether
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1 alcohol -> ether
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2 primary alcohols + strong acid (dehydration) good for symmetrical ether
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3 alcohol -> ether
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H2SO4___ethanol
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alkoxide -> ether
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alkoxide + alkyl bromide = SN2
best w/ 1 alcohol, ok with 2, doesn't occur with 3 |
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Alkene -> epoxide
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1. Br2__H2O
2. NaH |
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Nucleophilic ring opening of epoxides
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nucleophiles: RO-, RS-, CN-, N3
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Alkene -> epoxide
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McPBA (butterfly mechanism)
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Alkene -> glycol
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OsO4___TMAO
TMAO = trimethyl amine oxide |
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1 or 2 alcohol -> alkyl bromide
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PBr3
good w/ acid sensitive reagents |
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1 or 2 alcohol -> alkyl chloride
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SOCl2
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Alcohol -> alkyl halide
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H-X (X= halide)
2 and 3 alcohol react by SN1 1 require heat (1 carbocation) |
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Alkene -> alcohol
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H2SO4
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Alkene -> anti-markovnikov addition of Br
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HBr, peroxides
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Alkene -> Alkane
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H2___Pd/C
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Alkyne -> alkyl halide
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HBr____CH2Cl2
=geminal bromide * good for grignard |
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2 alcohol -> Ketone
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Na2CrO4 + H3O+
(redox reaction) |
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glycol -> ketone
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pinacol rearrangement
H2SO4 |