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Level 170

Nomenclature & Isomerism


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Propanal, Propanone, Cyclopropanol
Give example of three functional group isomers.
Aldehydes, Ketones and Cycloalcohols
What organic molecules are functional group isomers of each other?
E and Z isomer e.g. E pent-2-ene and Z pent-2-ene
When asked to draw pairs of stereoisomers, what should be drawn?
Propene, Cyclopropane
Chemical C is a HYDROCARBON with molecular formula C3H6, name 2 functional group isomers.
Stereoisomerism
What is optical isomerism?
Why are racemic mixtures formed?
equal chance of nucleophile attacking above or below carbonyl group.
Why are drugs only one enantiomer?
Has to bind to active site on enzymes/ receptors on cells (specific shape)
Asymetic carbon
What structural feature in a molecule gives rise to optical isomerism?
Drug is more effective, need smaller doses. Fewer side- effects.
Suggest two reasons why the pure DOPA enantiomer is used in preference to the racemate?
isomer
a compound with the same molecular formula as another compound, but a different arrangement of the atoms
Chain isomers
Same number of carbon atoms but different branching patterns
Position isomer
Same carbon skeleton but functional group in different place
Functional group isomerism
Same molecular formula but carbon atoms bond to form different functional groups
stereoisomers
isomers with same connectivity but different orientation of atoms in space
E/Z and optical
Types of stereoisomers
Double bonds cannot rotate
How do E/Z isomers form
E isomers
Same group on different sides of double bond
Z isomers
Same group on same side of double bond
optical isomers
molecules that differ three-dimensionally by the placement of substituents around one or more atoms in a molecule
Optically active
Affects light
Effects on plane polarised light
One optically active isomer rotates light clockwise, the other the same about anticlockwise
Enantiomer
An optical isomer
Racemate
50:50 mixture of both enantiomers
carboxylic acid
A compound that contains the carboxyl grp, --COOH
Acyl choride
oyl chloride
ester
An acid derivative with an alkyl grp replacing the acid proton.
Acid anhydride
oic anhydride
alcohol
A compound that contains a hydroxyl grp bonded to a carbon atom; R--OH
aldehyde
A carbonyl group with one allkyl grp and one H
ketone
A carbonyl grp with 2 alkyl groups attached
Alkene
ene
Nitro
Nitro-
Phenyl
-benzene or phenyl-
Amino-
Primary amine
Tertiary amine
N,N-di amino-