18 - carbonyl compounds Flashcards
aldehyde formation
. primary alcohol oxidation
primary alcohol + oxygen from oxidising agent => aldehyde + water
. oxidising agent = pot. dichromate with sulfuric acid
. need heat
. orange to green (Cr3+ ions)
. immediately distill off aldehyde to prevent turning to carboxylic acid
ketone formation
. secondary alcohol oxidation
secondary alcohol + oxygen from oxidising agent => ketone + water
. oxidising agent = pot. dichromate with dilute sulfuric acid
. need heat
. orange to green (Cr3+ ions)
carbonyl atoms in aldehydes and ketones
. aldehyde: on the side
. ketone: bonded to 2 atoms
naming aldehydes and ketons
aldehydes: - al
ketones: -one
reduction of aldehydes and ketones
aldehyde + reducing agent => primary alcohol
ketones + reducing agent => secondary alcohol
reducing agent conditions for aldehyde/ketone reduction
. warm NaBH4
. LiAlH4 dissolved in try ether at rtp (reacts in water)
aldehye/ketone + HCN (heat)
nitrile formed
can nitriles be easily hydrolysed
yes, make carboxylic acids
nitrile + HCl + H2O => carboxylic acid + NH4Cl
reflux
2 - hydroxynitrile
the product from the nucleophilic addition of hydrogen cyanide to a carbonyl compound
test for carbonyl group
2,4 - DNPH
. gives orange ppt.
test to distinguish between an aldehyde and ketone
Tollen’s reagent
. Ag+ ion = ox. agent
. aldehyde = silver mirrored formed (redox)
. ketone = no change/remains colourless (no redox)
Fehling’s solution
. alkaline
. Cu2+ ions = oxidising agent
. aldehydes = blue to orange/red opaque (oxidised)
. ketones = no change/remains blue (not oxidised)
forming tri-oodomethane
. CH3CO- group
. reagent = alkaline solution of iodine
. steps: carbonyl compound halogenated, intermediate hydrolysed, yellow ppt formed
. crystals have melting point 119°C
infrared spectroscopy
a technique for identifying compounds based on the change in vibrations of particular atoms when infrared radiation of specific frequencies is absorbed
machine used = spectrophotometer
resonance frequency
the frequency of absorption of radiation which stimulates larger vibrations in bonds to allow the absorption of energy
infrared spectroscopy graph
y axis = absorbance
X axis = wave number