ch 8 carboxylic acid derivatives reagents

primary alcohol + KMnO4

carboxylic acid

primary alcohol + H2CrO34

carboxylic acid

primary alcohol + CrO3 / H2SO4

carboxylic acid

alkyl halide + 1) Mg 2) CO2 3) H3O+

carboxylic acid

When will nucleophilic acyl substitution happen?

When the reacting reagent is more nucleophilic or is a stronger base than the original group

is a good leaving group a strong or weak base?

weak base = more stable after accepting electron pair

list the functional groups in correct reactivity

(least reactive) amide < ester < acid anhydride < acid halide (most reactive)

amide + acidic aqueous solution in heat (amide hydrolysis)

carboxylic acid

carboxylic acid + SOCl2

acid chloride

carboxylic acid + PCl3

acid chloride

carboxylic acid + CCl2

acid chloride

carboxylic acid + acid chloride

acid anhyride

acid chloride or acid anhydride + 1) H3O+

carboxylic acid

acid chloride or acid anhydride + 1) NaOH 2) H3O+

carboxylic acid

acid chloride or acid anhydride + ROH, [H+]

ester

acid chloride or acid anhydride + 1) NaOR 2) H3O+

ester

acid chloride or acid anhydride + R2-NH

amide

acid chloride or acid anhydride + 1) excess LiAlH4 2) H3O+

primary alcohol

acid chloride or acid anhydride + 1) excess R-MgX 2) H3O+

tertiary alcohol

acid chloride or acid anhydride + R2-CuLi

ketone

What is Fischer Esterification?

carboxylic acid + alcohol and strong acid catalyst into ester + water

carboxylic acid + 1) ROH 2) strong acid catalyst or H+

ester + water

what is Saponification?

convert ester to carboxylic acid 

ester + H3O+

carboxylic acid

ester + 1) NaOH 2) H3O+

carboxylic acid

What is transesterification

the existing alkoxy group (can already be an ester or an alcohol) of the ester is replaced by a new alkoxy group

Two equivalents of a Grignard reagent + acid chloride

tertiary alcohol

Two equivalents of a Grignard reagent + acid anhydride

tertiary alcohol

Two equivalents of a Grignard reagent + ester

tertiary alcohol

Two equivalents of a Grignard reagent + carboxylic acid

no reaction because acid base chem

Two equivalents of a Grignard reagent + amide

no reaction because acid base chem

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, -70 C 2) H2O

aldehyde

acid chloride + 1) LTBA 2) H2O

aldehyde

primary amide + 1) Br2 2) NaOH

primary amine

nitrile + 1) LiAlH4 2) H3O+

primary amine

nitrile + 1) H3O+ 2) heat

carboxylic acid

nitrile + Grignard reagent

imine

nitrile + 1) Grignard reagent 2) H3O+ (acidic workup)

ketone

hydrogen cyanide (HCN) + aldehyde

cyanohydrin

hydrogen cyanide (HCN) + ketone

cyanohydrin