constitutional isomers dipole moment ( ) = partial charge (generally 10-10) * distance of separation (gen erally 10-8) 1 debye (D)

= 10-18 esu-cm percent ionic character = observed / theoretical higher percent ionic character, more reactive double bond --> higher percent ionic character... lone pair --> higher dipole moment (direction would be the same without lp) dipole moment --> greater attraction --> higher mp&bp h-bonding --> significantly higher mp&bp higher molecular weight --> more fleeting/transient dipole moments --> higher mp &bp branched --> smaller SA --> lower mp&bp 1. allylic lone pair 2. allylic positive charge 3. lone pair adjacent to positive charge 4. pi bond between different EN 5. conjugated pi bonds in a ring saturated [hydrocarbons] = alkanes delta h = change in enthalpy - delta h = heat of combustion cyclopropane - high energy due to angle strain (from small bond angles) & torsio nal strain (eclipsing H's; locked in eclipsed conformation) cyclobutane - less angle strain, more torsional (? but it can adopt slightly puc kered conformation) cyclopentane - less total strain than cprop&but but more than cyclohex cyclohexane - very small angle strain in both chair and boat conformations; chai r: all H's staggered; boat: torsional strain due to (1) many eclipsed H's & (2) flagpole interactions --> twist boat 1,3-diaxial interactions stereoisomers - diff compounds, diff properties, cannot be interconverted via co nformational change // differ in 3d spatial arrangement but not in connectivity constitutional isomers differ in connectivity chiral - not superimposable on mirror image if chiral, nonsuperimposable mirror image is called enantiomer chiral -- optically active enantiomers rotate light in equal amts and opposite directions specific rotation = [alpha] = alpha / conc (g/mL) * length (dm) temp and wavelength also affect specific rotation but not linearly (+) - dextrorotatory (d); (-) - levorotatory (l) diastereomers - same connectivity but not mirror images (ex. cis-trans) meso compounds - achiral: reflectional symmetry kahit may chirality centers