* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
Download Table of K Values a pK
Survey
Document related concepts
Homoaromaticity wikipedia , lookup
Bottromycin wikipedia , lookup
Enantioselective synthesis wikipedia , lookup
Asymmetric induction wikipedia , lookup
Wolff rearrangement wikipedia , lookup
Organosulfur compounds wikipedia , lookup
Elias James Corey wikipedia , lookup
Discodermolide wikipedia , lookup
Kinetic resolution wikipedia , lookup
Hydroformylation wikipedia , lookup
Petasis reaction wikipedia , lookup
Wolff–Kishner reduction wikipedia , lookup
Nucleophilic acyl substitution wikipedia , lookup
Transcript
Table of Ka Values Figure removed due to copyright reasons. pKa = (-) log Ka METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date) I OH - OH 1. BH3 OH 2. NaOH/H2O2 1. OsO4 2. H2O2 OH OH Hg(OAc)2 X2, H2O OH X OH METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date) O MgBr 1. R O OH H MgBr R 2. H2O, pH 7 MgBr R' 2. H2O, pH 7 O 1. R 1. R OR' 2. H2O, pH 7 HO R OH R' R METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date) 1. O Aldehydes H R OH 2. pH 7, H2O H R 1. O Na 2. pH 7, H2O R R OH Ketones R R 1. O epoxides R 2. pH 7, H2O OH R Alcohols, carbonyl compounds and carboxylic acids: REDUCTION Reduction: Addition of H2 (or H-), loss of O or O2 ; loss of X2 H H R C R H C OH H Primary alcohol H O NaBH4 R C or H Raney Ni/ H2 Aldehyde O LiAlH4 R C OH Carboxylic acid must convert OH to leaving group H H R C H R C OH R' Secondary alcohol R' must convert OH to leaving group R C R' H R or Raney Ni/ H2 R C R' Ketone H Li H Al H R" R" O NaBH4 C OH R' Tertiary alcohol H Lithium aluminium hydride Na H H B H H Sodium borohydride Comparison of Reducing Agents • LiAlH4 is stronger. • LiAlH4 reduces more stable compounds which are resistant to reduction. Alcohols, carbonyl compounds and carboxylic acids: OXIDATION Oxidation: loss of H2, addition of O or O2, addition of X2 (halogens) H H R C H R R OH H H C PCC H R' R C OH H2SO4 R' Secondary alcohol R C H2SO4 C OH Carboxylic acid Aldehyde Na2Cr2O7/ O Na2Cr2O7/ H H Primary alcohol H R C O O R C X R' Ketone PCC R" R" R C R' H R C OH R' Tertiary alcohol X NH CrO3Cl-