Kaplan Organic Chemistry Chapter 2
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structural isomers/constitutional isomers
same molecular formula
share the same atomic connectivity
differ in rotation around single bonds
interconverted only by breaking bonds
two largest groups are antiperiplanar (opposite sides)
no overlap of atoms along the line of sight, opposite of eclipsed
what is the most stable conformation of cyclohexane?
chair conformation where two equatorial methyl groups are trans to each other.
does enantiomers have identical physical and chemical properties
yes except for optical acitivity and reactions in chiral environments
refers to the rotation of plane-polarized light by a chiral molecule.
- standardized units for comparison purposes
- equals observed rotation in degrees divided by concentration (g/ml) and path length
equal amounts of both enantiomers, no optical activity.
- non-mirror images
- molecule has two or more stereogenic centers and differs at some, but not all of these centers.
for molecule with n stereocenters, how many possible stereoisomers?
differences between diastereomers and enantiomers
- diastereomers have diff chem properties
- rotate plane-polarized light but the magnitude is not equal and opposite to another diastereomer
substituents differ in position around an immovable bond
E and Z forms
used for compounds with polysubstituted double bond
cahn ingold prelog priority rules
- based on atom bound to double bond (E/Z)
- higher the atomic number, more priority
what does horizontal and vertical lines represent in Fischer projection
- horizontal lines (pointing out)
- vertical lines (bonds going into the page)
assigning R and S
any time two groups are switched on a chiral carbon, the stereochemistry is inverted.
what changes the absolute conformation?
when reactant and product has different stereochemistry (R to S)
stays the same when bonds of stereocenter are not broken, when positions of chiral carbons are maintained.
can E and Z be diastereomers?
yes b/c they have the same connectivity
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