Carboxylic acid Derivatives

primary alcohols + KMnO4 or H2CrO4 or CrO3/H2SO4 (strong oxidizing agent)

synthesis of carboxylic acids

alkyl halide + Mg (make Grignard reagent)

1) CO2

2) H3O+

synthesis of carboxylic acids from alkyl halides

1) nuc attacks carbonyl carbon of carboxylic acid derivatives

2) molecule loses LG as it re-forms the carbonyl group

Nucleophilic acyl substitution

amide + acidic aqueous solution in heat

amide hydrolysis (amide to carboxylic acid)

carboxylic acid + SOCl2 or PCl3

carboxylic acid to acid chloride

carboxylic acid + acid chloride

carboxylic acid to acid anhydride

H3O+ or 1) NaOH 2) H3O+

acid chloride/ acid anhydride to carboxylic acid

ROH, [H+] or 1) NaOR 2) H3O+

acid chloride/ acid anhydride to ester

R2NH

acid chloride/ acid anhydride to amide

1) xs LiALH4 2) H3O+

acid chloride/ acid anhydride to primary alcohol

1) xs RMgX 2) H3O+

acid chloride/ acid anhydride to tertiary alcohol

R2CuLi

acid chloride/ acid anhydride to ketone

carboxylic acid + ROH, [H+]

fischer esterfication (carboxylic acid to ester)

ester + 1) NaOH 2) H3O+

saponification (results in carboxylic acid)

ester + alkoxide nuc (basic conditions) or alcohol (acidic conditions)

transesterification (change alkoxy group of an ester)

acid chloride, acid anhydride, or ester + grignard reagent (2 equivalents)

grignard reactions

1) LiAlH4

2) H3O+

reduction of ester, acid chloride, + amide

1) DIBAL-H, -70 degrees Celsius

2) H2O

ester to aldehyde

1) LTBA

2) H2O

acid chloride to aldehyde

primary amide + Br2, NaOH

Hoffmann rearrangement (makes a primary amine with 1 less carbon atom)

alkyl halide + cyanide ion

formation of nitriles

nitrile + 1) LiAlH4 2) H2O

reduction of nitriles to primary amines

nitirile + H3O+, heat

nitrile to carboxylic acid

nitrile + grignard reagent (makes ketone) + H3O+

nitrile to ketone

NaCN, HCN + aldehyde or ketone

cyanohydrin formation