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40 Cards in this Set
- Front
- Back
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Make -OH into a good L.G.
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Need alcohol
Reagents: Ts-Cl/pyr |
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Oxidize a 2° alcohol to a ketone
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Reagents:
PCC Swern KMnO4 HNO3 |
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Oxidize a 1° alcohol to an aldehyde
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Reagents:
PCC |
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Oxidize a 1° alcohol to a carboxylic acid
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Reagents:
Chromic acid KMnO4 HNO3 |
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Form a strong Nu: from an -OH
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Need alcohol
Reagents: Na K NaH |
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Make an alkoxide from an -OH
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Need alcohol
Reagents: Na K NaH |
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Form a good electrophile from an alcohol
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Need 1° alcohol and strong acid
Reagents: HBr (Sn2 mech.) |
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Replace an -OH with -NH2
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Need 1° or 2° alcohol
Reagents: 1. Ts-Cl/ pyr 2. excess NH3 |
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Replace an hydroxyl group with an halogen w/ no rearrangement
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Reagents:
SOCl2 PX3 PX5 P/I2 |
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Remove a vicinal -H and -OH to from a double bond
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Reagents:
H+, Δ (Cis & trans products possible, rearrangement possible - C+ intermediate) |
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Add 2 -H with syn addition
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Reagents:
H2 / Pt H2 / Pd H2 / Ni |
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Reduce an alcohol
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1. TsCl/pyr
2. LAH |
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Replace an hydroxyl group with an halogen with rearrangement
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1. H-X
(2. - H2O, ↬) |
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Make a symmetrical ether
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Need 1° or CH3 alcohol
Reagents: H+ (Sn2 mech.) |
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Make a 2-cyclopentylmethanol into a cyclohexene
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H+, Δ
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Replace an halogen with an -OH and invert stereochem.
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Need SN2 conditions
Reagents: KOH NaOH strong Nu: |
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Add -OH and -H Markovnikov
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Need alkene
Reagents: 1. Hg(OAc)2, H2O 2. NaBH4 Non-rearrangeable mercurinium ion intermediate (H2O attacks more substituted side) |
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Add -OH and -H Markovnikov with rearrangement
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Need alkene
Reagents: H+/H2O H2SO4/H2O H3O+ C+ Intermediate |
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Add -OH and -H anti-Markovnikov and syn
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Need alkene
1. BH3 ⋅ THF 2. H2O2, NaOH |
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Make a diol with syn addition
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Need alkene
OsO4, H2O2 1. KMnO4 (mild) 2. -OH/ H2O |
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Make a diol with anti addition
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1. peroxy acid (ex. MCPBA)
2. H3O+ Epoxide intermediate |
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Make an alcohol from an alkyne
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Need terminal alkyne
1. NaNH2 2. aldehyde OR ketone 3. H3O+ |
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Form a Na or K alkoxide
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Need an alcohol
Reagents: Na° K° NaH NaH2 |
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Add an alkyl group to sth
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Need alkyl halide and Mg or Li
1. Mg/ether (ex. THF) OR 1. Li Need carbonyl group 2. (ether) (Grignard attacks less substituted side) 3. H2O |
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Form a 1° alcohol
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Need formaldehyde
1. Grignard reagent / ether 2. H3O+ |
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Form a 2° alcohol
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Need aldehyde
1. Grignard reagent / ether 2. H3O+ |
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Form a 3° alcohol
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Need ketone
1. Grignard reagent / ether 2. H3O+ OR ester/acid chloride 1. Grignard reagent / ether 2. Grignard reagent / ether 3. H3O+ |
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Form a 1° alcohol from an epoxide
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Need epoxide
1. Grignard reagent / ether 2. H3O+ |
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Replace a 3° halide with an alcohol
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Need 3° halide ∴ Sn1 Mech.
H2O / AgNO3 |
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Add Cl or Br to an alkane at most substituted C
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Need sp3 hybridized C
Br2 OR Cl2, Δ (Radical Intermediate) |
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Make an ether
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Need alkoxide and CH3/1° alkyl halide
(Sn2 Mech.) |
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Reduce an alkyl halide to an alkane
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Need alkyl halide and Mg or Li
1. Mg/ether OR 2 Li 2. H2O |
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Reduce a ketone/aldehyde to an alcohol
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1. NaBH4 / CH3OH or ether
1. LAH 2. H2O 2. H3O+ |
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Reduce a carboxylic acid/ester to an alcohol
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1. LAH
2. H2O |
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Reduce a ketone/aldehyde to alcohol AND eliminate C=C double bonds
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H2/Pt
H2/Pd H2/Ni |
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Lengthen an ethylene oxide by 2 carbons and an -OH
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Need Grignard reagent
1. Epoxide ring (CH2 O CH2) 2. H3O+ |
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Make a double bond from an alkyl halide
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Need vicinal, anti H and halogen OR vicinal, anti 2 halogens
Reagents: strong B: |
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Make a double bond and lose an -OH
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H2SO4 / H3PO4
C+ intermediate |
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Dehydrate a diol and form a carbonyl
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Need vicinal diol
Reagents: H+ |
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Cleave an alkene into 2 carbonyl groups
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Need alkene
1. OsO4 / H2O2 Or diol 2. HIO4 Need alkene 1. O3 2. DMS |
