reactions_we_learned_in_chemistry_301

reactions_we_learned_in_chemistry_301 - KOH / ∆ / ethanol...

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Reactions We Learned in Chemistry 301, Spring 2008 Unit II S N 2, S N 1, E1 and E2 reactions Conversion of 3 o alcohols to halides: HCl or HBr (conc., 0 o C) Conversion of 1 o or 2 o alcohols to chlorides: SOCl 2 / pyridine Conversion of 1 o or 2 o alcohols to bromides: PBr 3 / ether Radical halogenation: Br 2 / h ν Unit III Markovnikov addition of HBr or HCl in ether to alkenes Addition of Cl 2 or Br 2 in CH 2 Cl 2 to alkenes Addition of Br 2 , Cl 2 , or I 2 in H 2 O to alkenes Addition of Br 2 , Cl 2 , or I 2 in alcohol to alkenes Markovnikov hydration of alkenes with rearrangement: H 2 SO 4 (cat.) / H 2 O Markovnikov hydration of alkenes without rearrangement: 1. Hg(OAc) 2 / H 2 O; 2 . N a B H 4 Anti-Markovnikov hydration of alkenes: 1. BH 3 -THF 2. H 2 O 2 / NaOH (aq.) Epoxidation of alkenes: m -CPBA / CH 2 Cl 2 Syn-dihydroxylation of alkenes: 1. OsO 4 2. NaHSO 3 / H 2 O Anti-dihydroxylation of alkenes: 1. m -CPBA / CH 2 Cl 2 2. NaOH / H 2 O Hydrogenation of alkenes: H 2 / PtO 2 in ethanol Ozonization of alkenes: 1. O 3 / -78 o C / CH 2 Cl 2 2. Zn / H 2 O or 2. H 2 O 2 / H 2 O (acetic acid also ok) Dehydrohalogenation of alkyl halides (to produce alkenes):
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Unformatted text preview: KOH / ∆ / ethanol Dehydration of alcohols (to produce alkenes): H 2 SO 4 or H 3 PO 4 / ∆ P O C l 3 / pyridine Addition of HCl or HBr in ether to alkynes Addition of Cl 2 or Br 2 in CH 2 Cl 2 to alkynes Markovnikov hydration of alkynes: HgSO 4 / H 2 SO 4 / H 2 O Anti-Markovnikov hydration of alkynes: 1. BH 3-THF 2. H 2 O 2 / NaOH / H 2 O Hydrogenation of alkynes to cis-alkenes: H 2 / Lindlar’s catalyst Hydrogenation of alkynes to trans-alkenes: Li or Na / NH 3 (l) Dehydrohalogenation of dihalides to alkynes: 1. NaNH 2 / NH 3 (l) 2. H + / H 2 O (if terminal alkyne) Formation of acetylide anions: NaNH 2 / NH 3 (l) Alkylation of acetylide anions: Connect sp-hybridized C to primary C Oxidation of 1° alcohols to aldehydes , 2° alcohols to ketones: PCC / CH 2 Cl 2 Oxidation of 1° alcohols to carboxylic acids , 2° alcohols to ketones: Na 2 Cr 2 O 7 / H 2 SO 4 / acetone (Jones’ reagent)...
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This note was uploaded on 03/21/2010 for the course CHEM 301 taught by Professor Morrow during the Fall '08 term at New Mexico.

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