Reactions_Frequently_Encountered

Reactions_Frequently_Encountered - Alcohols to Aldehydes:...

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Decarboxylation of ! -diacds. HOOC COOH R H Heat HOOC—CH 2 R H + R O R' COOH H R O H R' H Heat H + Decarboxylation of ! -ketoacds. R OH O .. .. .. R'OH + H + R OR' O .. .. .. .. + H 2 O Esterification R OH O .. .. SOCl 2 or PCl 5 + R Cl O Synthesis of Acid Chlorides RCOOH 1. LiAlH 4 , ether 2. H 3 O + RCH 2 OH Reduction of Carboxylic Acids Carbonation of Grignard reagents and organolithium compoumnds R—MgX 2. H 3 O R—COOH R—Li 1. CO 2 2. H 3 O R—COOH 1. CO 2 RCH 2 OH Oxidizing agent RCOOH Oxidizing agents: aqueous CrO 3 , KMnO 4 , K 2 Cr 2 O 7 , Na 2 Cr 2 O 7 General Oxidation of Alcohols RCHO Oxidizing agent RCOOH Oxidizing agents: aqueous CrO 3 , KMnO 4 , K 2 Cr 2 O 7 , Na 2 Cr 2 O 7 , Ag + General Oxidation of Aldehydes Reactions Frequently Encountered X O 1. (CH 3 ) 2 CHCH 2 ] 2 AlH DIBAH 2. H 3 O + H O Reduction of Carboxylic Acid Derivatives with DIBAH Cl O R O R 2 CuLi Addidition of Lithium Organocuprates PCC R OH R O H CH 2 Cl 2 Oxidation of Primary Alcohols to Aldehydes: PCC CrO 3 (pyridine) 2 R OH R O H CH 2 Cl 2 Oxidation of Primary
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Unformatted text preview: Alcohols to Aldehydes: Collins Reagent R OH Na 2 Cr 2 O 7 aq. H 2 SO 4 R OH O Oxidation of Primary Alcohols to Carboxylic Acids: Cr(VI) reagents in aqueous acid. Can also use permanganate in basic solution. Na 2 Cr 2 O 7 aq. H 2 SO 4 R OH R R O R Oxidation of Secondary Alcohols to Ketones: Using dichromate. Can also use PCC, Collins Reagent; Cr(VI) reagents in aqueous acid or permanganate in basic solution. R OH SOCl 2 R Cl R R Conversion of Alcohols to Halides R OH PX 3 R X R R Conversion of Alcohols to Halides O H 2 C CH 2 RMgBr + then H 3 O + RCH 2C H 2 OH Addition of Organomettalic Reagents to Epoxides H 3 O + RMgBr RH Protonolysis of Grignard Reagents...
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