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Unformatted text preview: METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date)
OH I - OH 1. BH3 OH H+/H2O OH 2. NaOH/H2O2
2. H2O2 OH OH 1. mCPBA OH 2. H+/H2O SYN
O Aldehydes OH H R ANTI H
R O Na OH Ketones R R R
O epoxides OH R
R OH ELECTROPHILIC AND NUCLEOPHIC CARBON
Methylmagnesium bromide d- H3 C d+ Mg Br Methyl lithium Methyl chloride d- d+ d+ H3 C Li H3C d- Cl TYPICAL ELECTROPHILES
Methyl chloride d+ H3C d- Cl acetone O dd+ Alcohols, carbonyl compounds and carboxylic acids:
Reduction: Addition of H2 (or H-), loss of O or O2 ; loss of X2
R C R H C OH H
Prim ary alcohol H O NaBH4 RC
Rane y Ni/
Aldehyde O LiAlH4 R C
OH Carboxylic ac id mus t convert OH to
leaving group H H
R C H R C OH R'
Secondary alcohol R' mus t convert OH to
leaving group R C
R' H R or
Rane y Ni/
H2 R C
R' Ke tone H Li H A l H R" R" O NaBH4 C OH R'
Terti ary alcohol H
Li thi um al umi nium
hydri de Na H
H H Sodi um bor ohydri de Comparison of
• LiAlH4 is stronger.
• LiAlH4 reduces more
which are resistant to
=> Alcohols, carbonyl compounds and carboxylic acids:
Oxidation: loss of H2 , addition of O or O2, addition of X2 (halogens)
R C H R H H
C R OH H R C OH R H2 SO4 C
OH Carboxylic ac id O
R C H2 SO4 R'
Secondary alcohol R' C Aldehyde Na2Cr2O7 / O Na2Cr2O7 /
Prim ary alcohol H R C O PCC X
R' Ke tone PCC
R' H R C OH R'
Terti ary alcohol X NH CrO3Cl- ...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.
- Spring '03