aldehydes and ketones
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18 Terms
What are aldehydes+ketones reduced to?
primary alcohols and secondary alcohols
Reagent and condition for reduction of aldehydes and ketones
NaBH4 aqueous
Q: Write an equation illustrating the reduction of ethanal to ethanol using [H] as the reducing agent
CH3CHO + 2[H] → CH3CH3OH
Q: Write an equation illustrating the reduction of butanone to butanol using [H] as the reducing agent
CH3CH2COCH3 + 2[H] → CH3CH2CHOHCH3
Why are aldehydes and ketones susceptible to attack by nucleophile?
contain planar polar carbonyl group in which C is delta positive atom.
The nucleophile is equally likely to attack the planar polar carbonyl group from above or below the plane. this means a 50:50 mixture of the 2 enantiomers is formed
Nucleophile
electron pair donor
Q: Name and outline the mechanism state reagent and conditions too when ethanal is reduced to ethanol (7)
nucleohiliv addition
NaBH4
aqueous
hydride ion
pg9 show mechanism
Outline the mechanism for reaction of propane with NaBH4
What is catalytic hydrogenation
in the presence of nickel catalyst hydrogen will add to the C=O bond.
Property of KCN
toxic
Q: Name and outline the mechanism when ethanal reacts with KCN and dilute sulfuric acid. Name product
pg 11
nucleophilic addition
KCN and dilute sulfuric
product is 2hydroxypropaneitrile
Q: Why is increasing carbon chain important?
for organic synthesis
mechanism practice on pg12
s
Q: When ethanal is reacted with KCN and sulfuric acid a racemic mixture is formed. WHY?
the planar carbonyl group is equally likely to be attacked by the CN- from above and below the plane so a racemic mixture forms
Q: How can you prove your product is a racemic mixture?
It will pass polarised light through the picture and no rotation of the light will occur
Q: Draw the two enantiomers of 2hydroxypropanenitrile
pg 14
Hydrolysis
breaking bonds using water
Draw the displayed formula of product formed when 2hydroxybutanenitrile is treated with hydrogen in presence of nickel catalyst
1aminobutan2ol