Isomerism and carbonyl compounds Flashcards
What is optical isomerism?
It is a type of stereoisomerism.
Optical isomers are non-superimposable mirror images of each other.
What is stereoisomerism?
Stereoisomers have the same structural formula but different spatial arrangement of atoms.
What is a chiral carbon?
It is a carbon atom that has four different groups attached to it.
What is a racemate/racemic mixture?
A mixture of equal amounts of enantiomers.
How is a racemic mixture formed from a compound containing a carbonyl group?
The carbonyl is planar
There is an equal chance that a nucleophile will attack from either above or below.
This means that an equal amount of enantiomer will be formed.
How do you know if a compound is an optical isomer?
Optical isomers rotate plane polarised light.
Why is a racemate not optically active?
Both enantiomers would rotate plane polarised light in equal and opposite directions
What is produced when an aldehyde is oxidised?
Carboxylic acid
Which reagents can be used to distinguish between aldehydes and ketones?
Tollen’s reagent
Fehling’s solution
What is the observation when Tollen’s reagent is used to test for aldehydes and ketones?
Aldehyde- silver mirror formed
Ketone- no visible change
What is the observation when Fehling’s solution is used to test for aldehydes and ketones?
Aldehyde- brick red precipitate
Ketone- no visible change
What are the conditions for the reduction of aldehydes and ketones back to alcohols?
NaBH4
in water with methanol
What are the conditions to produce hydroxynitriles?
KCN
followed by dilute acid
What is formed when aldehydes and unsymmetrical ketones react with KCN followed by a dilute acid?
A mixture of enantiomers
Identify the hazards of working with KCN
it is an irritant
extremely dangerous if ingested or inhaled
it can react with moisture to produce hydrogen cyanide which is a highly toxic gas