carbonyl Flashcards
oxidation of carbonyls
aldehydes can be oxidised to carboxylic acids
ketones cannot
reduction of carbonyls
LiAlh4 (or NaBH4) in dry ether
nucleophilic addition
undergo nucleophilic addition to forma hydroxy nitrile
reaction forms a raecemic mixture
solubility of carbonyls in water
Smaller aldehydes and ketones are soluble despite lack of hydrogen bonding
solubility decreases with increasing chain length
carbonyl test: Acidified potassium dichromate
aldehydes oxidised to carboxylic acid
orange dichromate (VI) into green chromium (III)
ketones show no change because cannot be oxidised
carbonyl test: 2, 4, DNP
aka brady’s reagent
reacts with all carbonyls to form and orange precipitate
Fehling’s solution
contains aqueous Cu2+ ions into Cu+ ions
blue solution to red ppt
ketones show no change because cannot be oxidised
tollens reagent
aldehydes oxidised to carboxylic acids
ketones show no change bc cannot be oxidised
colourless solution silver mirror
Iodine in the presence of alkali (iodoform)
Iodine in the presence of alkali
pale yellow precipitate of CH3I
formation of carboxylic acid by hydrolysis of nitriles
under acidic conditions
carboxylic acid and ammonium salt
Alkaline conditions produce a carboxylate ion and ammonia
reduction of carboxylic acids
strong reducing agent e.g. LiAlH4 in dry ether forms a primary alcohol
neutralisation of carboxylic acid
Carboxylic acids are weak acids, and so react with bases to form neutral salts
e.g.
CH3COOH + NaOH → CH3COO- +Na + H2O
halogenation of a carboxylic acid
PCl5 (strong halogenating agent) replaced the COOH group with a COCl group
acyl chloride is formed
esterification of a carboxylic acid
in the presence of an acid catalyst
reacts with alcohols to from an ester
this is a slow reversible reaction
reaction of acyl chloride with water
forms carboxylic acid and hydrochloric acid (misty white fumes)