aldehydes and ketones Flashcards
general formula aldehydes and ketones
CnH2nO
fuctional group
aldehydes and ketones both contain the carbonile bond (=O)
where is the functional carbonie bond on an aldehyde
end of chain
where is the functional carbonile bond on ketones
middle of chain
what are aldehydes and ketones with the same number of carbon atoms, in relation to eachother
functional group isomers
how can aldehydes and ketones be prepared
oxidation of alcohols
what are aldehydes readily oxidised to
carboxylic acids
what 3 reagents can be used to oxidise an aldehyde to a carboxylic acid
- acidified potassium dichromate and warm
- fehlings solution and warm
- tollens reagent and warm
what observations with acidified potassium dichromate and warm and aldehyde
orange>green
what observations with fehlings solutions and warm and aldehyde
blue solution>brick red ppt
what observations with tollens reagent and warm and adlehyde
silver mirror
what are tollens reagent and fehings solutions used as
chemical tests to distinguish between aldehydes and ketones
how are tollens and fehlings used to distinguish between aldehydes and ketones
ketones cannot be further oxidised and will not react with either tollens reagent/fehlings solution
what complex ion does tollens reagent contain
Ag(NH3)2+
why is a silver mirror seen when an aldehyde is warmed with tollens
the aldehyde is oxidised to a carboxylic acid and the silver ions are reduced to silver metal
equation for reaction of aldehyde with tollens
RCOH+(O)>RCOOH
Ag+aq>Ags
what does (O) represent in equation for aldehyde and tollens
oxidising agent- tollens
which ions does fehlings solution contain
cu2+
why is a brick red ppt seen when an aldehyde is warmed with fehlings
aldehyde is oxidised to a carboxylic acid and the copper ions are reduced to copper 1 oxide (cu2o)
what does the presence of the delta+ c atom in aldehydes and ketones mean
theyre susceptible to attack by nucleophiles
why do aldehydes and ketones have a delta+ c atom
polar C=O bond
what is a nucleophile
an electron pair donor
how can the nucleophile attach the delta+ carbon
forming a new covalent bond, an addition reaction then occurs across the double bond
what can aldehydes and ketones be reduced to
alcohols
how does the reduction of aldehydes and ketones occur
via a nucleophilic addition mechanism
reagent for reduction of aldehydes and ketones
NaBH4
conditions for reduction of aldehydes and ketones
aqueous solution
GENERAL EQUATION FOR REDUCTION OF ALDEHYDES
RCOH + 2[H] > RH2COH
what are aldehydes reduced to form
primary alcohols
what is the reducing agent often simplified as in balanced equations
[H]
general equation for reduction of ketones
RCOR + 2[H] > RCHOHR
name of mechanism for reduction of aldehydes/ketones
nucleophilic addition
nucleophile for reduction of aldehydes/ketones
hydride ion H-
how can aldehydes and ketones be converted into hydroxynitriles
addition of HCN
mechanism for addition of HCN to aldehyde/ketone
nucleophilic addition
reagents for addition of HCN
KCN followed by dilute acid
general equation for addition of HCN to aldehydes
RCOH + HCN > RCHOHCN
general equation for addition of HCN to ketones
RCOR + HCN > RCOHRCN
what will reacting an aldehyde/ketone with cyanide increase
the length of the carbon chain
nucleophile in addition of HCN to aldehyde/ketone
cyanide ion CN-
why is KCN used as opposed to HCN
HCN TOXIC GAS
KCN ALSO TOXIC BUT IS AN IONIC SOLID- READILY DISSOLVES TO FORM SOLUTION
what forms when aldehydes and unsymmetrical ketones undergo reaction with KCN followed by dilute acid
a racemic mixture of 2 enantiomers
racemic mix
a mixture of equal amounts of the two enantiomers
what are enantiomers
optical isomers
optical isomers
non superimposable mirror imahes
how does the shape of the aldehyde/unsymmetrical ketone lead to a mixture with equal amounts of the two enantiomers being formed
trig planar- attack from each side equally likely