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Carbonyl Synthesis Summary

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Reaction Summary

Oxidation of alcohols with weak oxidizer

a)

oxidation of primary alcohol to aldehyde with pcc

b)

oxidation of secondary alcohol to ketone with pcc

c)

Failed oxidation of tertiary alcohol

Swern oxidation and DMP are weak oxidizers like PCC.

Oxidation of alcohols with strong oxidizer

d)

oxidation of primary alcohol with Na2Cr2O7 making carboxylic acid

e)

oxidation of secondary alcohol with Na2Cr2O7 making ketone

f)

Failed oxidation of tertiary alcohol

Reduction of carboxylic acid

g)

reduction of carboxylic acid with LAH to make alcohol

h)

reaction of carboxylic acid with thionyl chloride to make acid chloride then LiAlH(OtBu)3 to make aldehyde

i)

Esterification of carboxylic acid then reaction with DIBAL-H to form aldehyde

Alkene/Alkyne oxidations

j)

alkyne reacting with HgSO4 to form markovnikov ketone

k)

alkyne reacting with Sia2BH to form antimarkovnikov aldehyde

l)

ozonolysis of cyclopentene

m)

ozonolysis of alkyne

n)

KMnO4 further oxidation of alkene

o)

KMnO4 oxidation of alkyne to form diketone

p)

further oxidation of alkyne with KMnO4 to form carboxylic acids

q)

Periodic acid (HIO4) cleavage of glycol to form carbonyl compounds

1,3-dithiane aldehyde/ketone synthesis

r)

1,3-dithiane to form ketones and aldehydes

Ketones from carboxylic acids

s)

Ketone formation from carboxylic acids using LiOH and RLi

Ketones from nitriles

t)

Ketone from nitriles from reacting with Grignard reagent

Carboxylic acids from Grignard reagent and CO2

u)

Carboxylic acids from Grignard reagent reacting with CO2

Carboxylic acids from the hydrolysis of nitriles

v)

Carboxylic acids from the hydrolysis of nitriles

Carboxylic acids from the permanganate oxidation of alkylbenzene

w)

Carboxylic acids from the permanganate oxidation of alkyl benzene

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