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isomers with same connectivity but different orientation of atoms in space
conformational isomers
stereoisomers that can be converted into one another by rotation around a single bond
configurational isomers
stereoisomers that cannot be converted into one another by rotation around a single bond
geometric isomers
molecules that are locked into their spatial positions with respect to one another due to a double bond or ring structure
constitutional isomers
compounds that have the same molecular formula and different connectivity
optical isomers
molecules that differ three-dimensionally by the placement of substituents around one or more atoms in a molecule
due to this interconversion, alkyl amines are not
An atom that gives rise to stereoisomers when its groups are interchanged. Asymmetric carbon atoms and double-bonded carbons in cis-trans alkenes are the most common stereocenters.
doesn't have 4 different substituents
can become chiral by replacing one group
both carbons on the double bond have different groups, first priorities on the same side
both carbons have different groups, the first priorities on opposite sides
constant in the ideal gas law, or ideal gas constant
groups 1 (alkali metals) and 2 (alkali earth metals) will only show "_" cloud electrons
A substrate with a single chirality center at the carbon attached to the leaving group will give rise to a pair of _______
two or more chiral centers
differ only in how their atoms are oriented in space
Converted by rotation
Configurational Isomer
Must Break bonds to convert
Stereogenic Center
Chiral, 4 different groups
More than one stereogenic center
molecule is achiral
Bacemic Mixture
50/50 of two enatiomers
Horizontal Out
a compound with the same molecular formula as another compound, but a different arrangement of the atoms
constitutional isomer
isomers with different bonding sequence
An optical isomer
chirality center
only atom that is the source of chirality (asymetric site)
asymetric carbon
carbon based chiral centers
position of lowest priority group
on the back of the stereocenter
r rotation
notation of clockwise rotation
s rotation
notation of counterclockwise rotation
d nomenclature
experimentally determined (+) rotation
l nomenclature
experimentally determined (-) rotation with plane polarized light
racemic mix
50/50 mixture of R and L
100% of one enantiomer
sign of a stereocenter
four different groups from one atom
number of groups to switch when showing an enantiomer
bonds on plane of paper
bonds to rotate to place last priority group in back for figuring out r and s nomenclature
non-superimposible image stereoisomer. Does not share physical properties and can be isolated by normal means.
Meso compound
an achiral molecule that contains a chirality center. mirror image is superimposible
lowest priority group in front
reverse convention for r and s rotation
keep rotation convention from wedge-dash
lowest priority group is on vertical
reverse convention from wedge-dash
lowest priority group is on horizontal
si face
counter-clockwise rotation for change of sp2 site
re face
clockwise rotation for change of sp2 site
one change in substituents can result in a chiral center
atom to image replacing one of two groups when describing prochirality of an sp3 with two of the same group
replacement of this group results in clockwise chirality
replacement of this group results in counterclockwise chirality