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O-Chem Chapter 3

AB
isomersdifferent compounds with same formulas
constitutional isomerssame formula butdifferent order fo attachment
stereoisomerssmae molecular formulas, same connectivity, different orientations in space (ex. cis, trans isomers in cycloalkanes)
chiralmolecule that is not superimposable on its mirror image
achirallacks chirality
plane of symmetryplane that divides an object so that one side is a reflection of the other
center of symmetrypoint where identical components of the object are located equidistant and opposite the point along any axis
enantiomersstereoisomers that are nonsuperimposable mirror images of eachother
stereocenter, stereogenic centeratom that has 4 different atoms or groups attached ot it
naming stereocenters with the R,S systematoms bonded to stereocenter given priority based on highest atomic number (or the first difference); atoms of double bonds are doubled and triple bonds are tripled; if groups are read clockwise its R, counterclockwise is S
n sterocenters give ? maximum stereoisomers2^n
diastereomersstereoisomers that are not mirror images of each other
meso compoundsachiral compound possessing two or more stereocenters, special symmetry (summetry that biscets the molecule into two mirror halves) that reduced the number of stereoisomers to fewer than the 2^n max
chiral cis and trans isomersstereoisomers that are mot mirror images, they are diastereomers
enantiomers properties in achiral environmentsidenitcal physical and chemical props, different rotation fo pp light
diastereomers in achiral or chiral environmentsdifferent physical and chemical props
optically acitvecompounds that rotate pp light, like all enantiomers
pp lightlight vibrating in only parallel planespolarimeter
polarimetermeasures the ability of a cmpd to rotate the pp light (light source, polarizing filter, analyzing filter, sample tube)
props rotation depends onconcentration, legth of sample tube, temp, solvent, wavelength fo light
observed rotationnumber of degrees through which a compound totated the pp light
dextrorotatorycmpd that rotated light to the right, (+)
levorotatorycmpd that rotated light to the left, (-)
specific rotationobserved rotation divided by (length x concentration)
racemic mixturemixture of equal amounts of two enantiomers, specific rotation is 0, optically inactive, (+-)
optical purityway to describe the composition of a mixture of anantiomers, specific rotation mixture / specific rotation pure x 100%
enantiomeric excess (ee)percentage difference in number of moles of each enantiomer in a mixture compared with the total number of moles of both, (%R-%S)
resolutionseparatoin fo racemic mixture into its enantiomers, by means fo diastereomeric salts (convert enantioners into two diastereomers which can be separated based on different phy/chem props with the use fo an enantiomerically pure chiral resolving agent) or enzymes as resolving agents (used as chiral chatalyts to synthesize pure enantiomers)
enzymeschiral catalysts
stereospecificreactions where only one enantiomer is produced


Wimberley Danforth Junior High

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