Organic Chemistry Carboxylic Acid Derivatives (DAT)
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34 Terms
Primary alcohol + KMnO4 —>
carboxylic acid
Primary alcohol + H2CrO4 —>
carboxylic acid
Primary alcohol + CrO3, H2SO4 —>
carboxylic acid
alkyl hallide + 1. Mg 2. CO2 3. H3O+ —>
carboxylic acid
List the carboxylic acid derivatives in order of increasing reactivity/decreasing stability
amide, ester, anhydride, acid halide
Carboxylic acid + SOCl2 —>
acid chloride
Carboxylic acid + PCl3 —>
acid chloride
Acid chloride + H3O+ —>
carboxylic acid
Acid chloride + 1. NaOH 2. H3O+ —>
carboxylic acid
Acid chloride + ROH, H+ —>
ester OR
Acid chloride + 1. NaOR, 2. H3O+ —>
ester
Acid chloride + R2NH —>
amide
Acid chloride + 1. excess LiAlH4 2. H3O+ —>
primary alcohol
Acid chloride + 1. excess RMgX 2. H3O+ —>
tertiary alcohol
Acid chloride + R2CuLi —>
ketone
Ester + 1. LiAlH4 2. H3O+ —>
primary alcohol
Acid chloride + 1. LiAlH4 2. H3O+ —>
primary alcohol
Amide + 1. LiAlH4 2. H3O+ —>
amine
Ester + 1. DIBAL-H, -70ºC 2. H2O —>
aldehyde
Acid chloride + LTBA —>
aldehyde
DIBAL specifically reduces what FG
ester
LTBA specifically reduces what FG
acid chloride
Primary amide + Br2, NaOH —>
primary amine
Saponification converts ___ to ___
ester to carboxylic acid
Fischer esterification converts ___ to ___
carboxylic acid to ester
Saponification is ___ (reversible/irreversible)
irreversible
Fischer esterification is ___ (reversible/irreversible)
reversible
Ester + 1. NaOH 2. H3O+ —>
carboxylic acid
Carboxylic acid + NaOH, H+ —>
ester
Alkyl halide + NaCN —>
nitrile
RCN + 1. LiAlH4 2. H2O —>
primary amine
Nitrile + RMgX, H3O+ —>
ketone
CN- + aldehyde/ketone —>
cyanohydrin
Nitrile + H3O+, heat —>
carboxylic acid