Carbonyl Compounds Flashcards
functional group
C=O
2 homologusseriesofcarbonyl compounds
dehydes
ketones
aldehydes general formula
Cn H2n+1 CHO
how is an aldehyde formed
by dehydrating an alcohol
general formula for ketones
Cn H2n+1 CO Cn H2n+1
R CO R’
ending for ketones
…anone
physical properties of ketones
simpler ketones have colourless liquids
simpler ketones dissolve in water due to hydrogen bonding
how are ketones prepared
oxidation of secondary alcohols by warming with acidified potassium dichromate
what types of reactions do ketones take part in
nucleophilic addition
condensation reactions
similar to aldehydes because of the carbonyl group in their structure
reaction of ketones with Fehling’s and Tollen’s solutions
no reaction because ketones cannot be easily oxidized
hence, reactions with these reagents are used to distinguish between aldehydes and ketones
compound name ending for aldehydes
…anal
what happens in nucleophilic addition of aldehydes and ketones
- the carbonyl C atom will be partially positive since it is bonded to the electronegative O atom
- the negatively charged particles (nucleophiles) are attracted to the C atom
- the nucleophile will add to the carbonyl C atom since this C atom is unsaturated
in the mechanism of nucleophilic addition,what is the slow step
as the nucleophile approaches the carbonyl compound, the pi bond is broken so the nucleophile bonds to the C atom and a negatively charged intermediate is formed
in the mechanism of nucleophilic addition, what is the fast step
the positively charged hydrogen bonds quickly to the negative O to complete the reaction
the reaction is done by adding a mixture of KCN and dilute acid to the aldehyde/ ketone, maintaining a temperature between 10-20 deg. C
condensation reactions of aldehydes and ketones
carbonyl compounds react with the general formula H2X
during the reaction, the reagent loses H2 and the carbonyl compound loses O
water is eliminated
the carbonyl C atom then bonds to the X
*a double bond is not broken
condensation reactions with 2,4-dinitrophenylhydrazine (2,4-dnp)
an orange or brown precipitate is formed
this is used to show the presence of a carbonyl group in the organic compound
oxidation of aldehydes process
aldehydes are easily oxidized by gently warming with H2SO4 and K2Cr2O7 or H2SO4 and KMnO7
what are aldehydes oxidized to
carboxylic acids
how can you test for the CHO group in a compound
- silver mirror test/ Tollen’s reagent
test with Fehling’s solution
test of aldehyde with fehling’s solution
forms a reddish brown precipitate
test of aldehyde with fehling’s solution
forms a reddish brown precipitate
silver mirror test with aldehydes
forms a silver precipitate
tollen’s reagent- AgNO3 + NH3
reducing agents used in reduction of aldehydes
- LiAlH4 (lithiumaluminiumhydride)
- NaBH4 (sodiumborohydride)
reduction of aldehydes
when an aldehyde is reacted with LiAlH4 in dry ether or NaBH4 in a mixture of H2O and CH3OH, the aldehyde is converted to a primary alcohol