CH 3 - Stereoisomerism and Chirality
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30 Terms
isomers =
same formula, different structures/properties
constitutional isomers
connection of atoms
stereoisomers
same connections, but different orientations in space
chirality =
handedness
non superimposable
think putting hands on top of each other
chiral compounds have
“handedness”, sometimes with dramatic consequences `
achiral =
no handedness
superimposable
think socks; can put on either foot
achiral objects contain
an element of symmetry
stereocenter
an atom where exchange of two groups produces a stereoisomer
flat molecules =
no chirality
chiral center
tetrahedral atom bonded to 4 different groups
enationmers
stereoisomers that are non superimposable mirror images
atropisomers
enantiomers that lack a chiral center and are locked due to hindered rotation
S configuration
counterclockwise/left
R configuration
clockwise/left
priority rules - the higher the atomic number,
the higher the priority
priority rules - priority is assigned at
the first point of difference
priority rules - atoms participating in a couple and triple bond are considered to be bonded to an
equivalent number of similar atoms by single bonds
diastereomers
stereoisomers that are not mirror images
refers to the relationship among two or more objects
meso compound
an achiral compound possessing two or more chiral centers that also has chiral isomers
Fischer projections - horizontal segments
represent bonds toward you
Fischer projections - vertical segments represent
bonds directed away from you
optical activity - observed rotation
the number of degrees, a, through which a compound rotates the plane of polarized light
optical activity - dextrorotatory (+)
refers to a compound that rotates the plane of polarized light to the right
optical activity - levorotatory (-)
referes to a compound that rotates the plane of polarized light tot the left
optical activity - specific rotation
observed rotation for a sample in a tube 1.0 dm in length and at a concentration of 1.0 g/mL
for a pure liquid, concentration is expressed in g/mL (density)
optical purity
a way of describing the composition of a mixture of enantiomers
enantiomeric excess
the different between the percentage of two enantiomers in a mixture