carboxylic acid → COOH derivatives

Carboxylic acid → symmetrical anhydride

1. SOCl2 pyridine heat

2. o^- carbonyl

or P2O5 or heat

Carboxylic acid → unsymmetrical anhydride

1. SOCl2 pyridine heat

2. o- carbonyl with c chain

carboxylic acid → thioester

-SH, H+ (or NaOH)

carboxylic acid → amide

DCC or EDEC, NH3 

carboxylic acid → ester

MeOH, H+ or 1. NaOH 2. CH3Br

carboxylic acid → aldehyde

   1.LiAlH4 

2. H3O+ 

3. PCC 

carboxylic acid → ketone

1.SOCl2

2. Gilmans

carboxylic acid → nitrile

1. DCC or EDEC, NH3

2. SOCl2

carboxylic acid → acid chloride

1. SOCl2, pyridine, heat

H3O+

reversal for all COOH deratives (NOT KETONES OR ALDEHYDES)

aldehyde → COOH 

KMNO4

Mild reducers

1.NaBH4, EtOH

2. NaHSO3, H2O

Strong Reducers

1.LiAlH

2. H3O+

aldehyde mild reducer

1 OH

aldehyde strong reducer

1 OH

ester strong reducer

1 OH

Ketone mild reducer 

2 oh 

Ketone strong reducer

2 OH

COOH strong reducer 

1 OH 

Strong oxidzer

Na2Cr2O7, H2SO4 CrO3,H2SO4. KMno4

mild oxidizer

Des martin DCM, Swern DCM, NaOCl, CH3CO2H PCC, CH2Cl

primary OH strong oxidzer

COOH

secondary OH strong oxidizer

ketone

tertiary OH strong oxidizer

no rxn

primary OH mild oxidizer

aldehyde

secondary OH mild oxidizer

ketone

tertiary OH mild oxidizer 

no rxn 

h2NNH2 koh

ketone aldehyde—> alkane

H2NNH2 h3o+ 

aldehyde / ketone —> c=n-nh2 

NaBH3CN

reducer for imines and enamines gets rid of double bonds