Stereoisomerism

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Flashcards on Stereoisomerism, created by J yadonknow on 05/01/2018.
J yadonknow
Flashcards by J yadonknow, updated more than 1 year ago
J yadonknow
Created by J yadonknow almost 7 years ago
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Question Answer
What are stereoisomers? Isomers who's atoms are connected in the same order but have a different arrangement in space
What is a chiral/achiral stucture? Superimposable/not superimposable at least 1 carbon, bonded to 4 different groups
What is the name of a chiral carbon atom? Asymmetric carbon/stereocentre
What is a racemate? A racemic mixture where the entantiomers are in 1:1 ratio
How can you tell if a reaction will produce a racemic mixture? If the achiral reactants for a chiral product
Why is this important medically? Many drugs are chiral, with only one enatiomer having the desired effect The opposite enatiomer may be biologically inactive or active, and produce undesired effects i.e. thalidomide
How do chiral molecules generally exist in nature? Usually only 1 enatiomer, all amino acids are chiral EXCEPT Glycine ENATIOMERICALLY PURE
How do you describe which enatiomer you're talking about? R/S system +/-(d/l) system based on polarisation of light D/L based on chemical degradation product
How do you use the R/S system? 1. Identify the stereogenic centre 2.Assign priority to each group based on AN of first atom of group 3. If 2 AN are the same, go to next atom 4. Arrange so lowest priority group is pointing away (pointing into plane of paper behind) 5. Use 1-2-3 to determine if it's clockwise (R) or anticlockwise (S) So now you can name it (S)-alanine
What do the various lines denote in terms of 3D orientation? Dashed line - into the plane of the paper wedge- bond out towards you solid- bond in plane of paper
How can you skip the bullshit stuff to tell if it's R or S? If the hydrogen is coming out at us in space, then we ignore it and count 1-2-3, and put the opposite of this rotation, so if 1-2-3 clockwise then it's S not R
What are the properties of enatiomers? Same physical properties except plane of polarisation rotation by S/R enantiomers Same chemical properties unless another chiral molecule is involved
What is (Anti)clockwise rotation of light polarity? What is important to keep in mind? clockwise=+ or d anticlockwise=- or l Just because an enantiomers is clockwise, DOESN'T mean it rotates light clockwise
What are Diastereoisomers? Stereoisomers that are NOT optically superimposable with one or more chiral centres can form multiple structures due to free rotation, which are isomeric
How do you derive the number of stereoisomers? 2^n
Draw a diagram showing relationship between enantiomers and diastereomers RS-SR Enant RR-SS Enant RS-SS Dia SR-RR Dia RS-RR Dia SR-SS Dia E- cute fit D-awkward grasp
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