Organic chemistry reagents acs – Flashcards
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NaH
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ROH to RO- Na+
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NaBH4, MeOH
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Ketone to alcohol
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H2/Pt
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Reducing to cis
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1. LAH 2. H2O
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Reducing to trans
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1. RMgX 2. H2O
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Add R group
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TMSCl, Et3N
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Protection group of alcohols
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TBAF
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Remove alcohol protecting group
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1. TsCl, py 2. NaBr
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Make water good leaving group. The sn2
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SOCl2, py
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Chlorination of alcohol
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H2SO4, heat
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Elimination
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-OEt
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Elimination
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Jones
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Secondary alcohol= ketone Primary alcohol= carboxylic acid
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PCC
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Primary alcohol= aldehyde
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1. Hg(OAc)2, H2O or ROH 2. NaBH4
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Markinov addition
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MCPBA
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Epoxide ring
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1. Br2, H2O 2. NaOH
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Epoxide ring
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NaOH, H2O
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Opening epoxide ring
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1. Nuc 2. H2O
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Opening epoxide ring
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HX
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Markinov addition
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HBr, ROOR
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Anti markinov
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1. BH3.THF 2. H2O2, NaOH
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Anti markinov n syn
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OsO4
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Syn OH addition
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Electro cyclic
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Syn hv syn Syn heat anti Anti heat syn Anti hv anti
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NBS heat
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Free radical bromination
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Na, CH3OH, NH3 Birch reduction
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Aromatic ring to two alkynes
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FeBr3, Br2
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Bromination of aromatic ring
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AlCl3, Cl2
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Chlorination of aromatic ring
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Fuming H2SO4
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Sulfonation of aromatic ring
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Dilute H2SO4
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Remove sulfonation of aromatic ring
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HNO3, H2SO4
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Nitration of aromatic ring
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1. KMnO4, NaOH heat 2. H3O+
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Methylbenzene to methyl carbolic acid
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HO--OH
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Acetal protecting group
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H2O
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Remove acetal protecting group
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Witting reaction
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C=C produced
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RCO3H
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Produced esters
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1. CO2 2. H3O+
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Grignard to carboxylic acid
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1. LDA 2. RX
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Alkylation to alpha Low temp less sub High temp more sub
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Sulfuric acid
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Proton source
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NaNH2
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Elimination
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PBR
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Bromination of primary alcohol
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Heat
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Cyclo reactions
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1. DIBAH 2. H2O
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Ester into aldehyde
