Optical activity o Active solution Chiral compound o Inactive solution Meso compound (achiral compound with two or more stereogenic centers) Meso compound with two stereogenic centers o Trans two groups on opposite sides of the ring; one up and one down Specific rotation o Specific rotation=[a]=a / l c=length of sample tube c=concentration
Optical activity o Active solution Chiral compound o Inactive solution Meso compound (achiral compound with two or more stereogenic centers) Meso compound with two stereogenic centers o Trans two groups on opposite sides of the ring; one up and one down Specific rotation o Specific rotation=[a]=a / l c=length of sample tube c=concentration
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Optical activity o Active solution Chiral compound o Inactive solution Meso compound (achiral compound with two or more stereogenic centers) Meso compound with two stereogenic centers o Trans two groups on opposite sides of the ring; one up and one down Specific rotation o Specific rotation=[a]=a / l c=length of sample tube c=concentration
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o Different ways to show a compounds arrangement of electrons
o Resonance vs. Isomer Resonance structures that differ in the arrangement of electrons Isomers differ in the arrangement of both the atoms and electrons. o Hybrid resonance structures Composite of all possible resonance structures Strain (Newman Projections) o Torsional strain An increase in energy due to eclipsing interactions o Steric Strain An increase in energy when atoms are forced too close to each other o Angle strain An increase in energy when tetrahedral bond angles deviate from 109.5 Newman Projections o Staggared Lower energy More stable o Eclipised Higher energy Less stable o Gauche conformations Higher in energy because of Steric strain Cis & Trans o Cis Two groups on the same side of the ring; both up or down o Trans Two groups on opposite sides of the ring; one up and one down Optical activity o Active solution Chiral compound o Inactive solution Achiral compound (no stereogenic centers) Meso compound (achiral compound with two or more stereogenic centers Racemic mixture (an equal amount of two Enantiomers Specific rotation o Specific rotation=[a]=a/l*c a=observed rotation l= length of sample tube c=concentration Enantiomeric excess o Ee= % of enantiomer - % of other enantiomer= a(mixture)/a(pure enantiomer)*100% Ee= enantiomeric excess