Lightiselectromagneticradiationthat
oscillatesperpendiculartoitsdirectionof
motion.
Theoscillationoflightcanberesolvedinto
twoperpendicularcomponents.
Whenlightispassedthroughapolarizer,
onlyoneofthetwoperpendicular
componentsoflightispassedthrough.This
lightisreferredtoasplanepolarizedlight.
Plane polarized light
Enantiomerscannotbedistinguishedonthebasisoftheirphysical
properties,suchasboilingpoints,meltingpoints,anddensities.
Enantiomerscanbedistinguishedbythewaytheyinteractwithplane
polarizedlight.
Whenplanepolarizedlightispassedthroughasampleofoneofthe
enantiomers,theplaneofpolarizationisrotatedeitherclockwiseor
counterclockwise.Whentheexperimentisrepeatedwiththeother
enantiomer,theplanepolarizedlightisrotatedanequalamount,butin
theoppositedirection.
Iffacingthelightsource:
Clockwiserotation:enantiomerisdextrorotary(+)
Counterclockwiserotation:enantiomerislevorotary ()
Thisinteractionwithlightiscalledopticalactivityandenantiomersare
oftencalledopticalisomers.
DiagramofaPolarimeter
Themeasuredrotation(indegrees)istheobservedopticalrotation,,ofthesample.
Thevalueof dependsupon:
Structureofthechiralmolecule
Concentrationofthechiralmolecule
Lengthofthesamplecell
Wavelengthofthelight
Solventused
Temperature.
Thespecificrotation[]ofasampleisdefinedforeachchiral
molecule(thevalueissolventdependent):
[ ]t
o
l c
where [ ] = specific rotation
t = temperature in degrees Celsius
= wavelength of incident light
(D = 589 nm, the yellow D line from Na)
= observed optical rotation in degres
l = sample container length in dm
c = concentration (g/ml)
Enatiomers havethesamespecificrotationbutwithdifferent
signal.
Opticalrotationindicatesenantiomeric composition
Aracemicmixtureisamixtureofequalamountsofthe+and
enantiomersofachiralcompound.Itshowsnonetrotationofplane
polarizedlight.
Whenoneenantiomerequilibrateswithitsmirrorimage,theprocessis
calledracemization.
Whenoneofthetwoenantiomersofachiralcompoundispresentina
mixtureinexcessovertheothertherewillbeanetrotationofplane
polarizedlight.
A50%enantiomerexcesswouldbedefinedasamixtureof75%one
enantiomerand25%oftheother[50%(+)with25%(+)and25%()].The
mixturewouldbecalled50%opticallypure.
Theopticalpurityofanenantiomerisdefined:
observed
% optical purity 100 enantiomer excess