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CHEM 301

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Term
Definition
constitutional/structural isomers   differ in their bonding sequence  
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stereoisomers   differ only in the arrangement of the atoms in space  
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cis-trans isomers   cis = same side, trans = opposite side *there must be 2 different groups on the sp2 carbon  
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pauli exculsion principle   each orbital may hold a max. of 2 e- w/ opposite spins  
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hund's rule   equal energy orbitals are half-filled, the fully filled  
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aufbau principle   filling up the energy level diagram one e- at a time, lower energy orbitals are filled before higher energy orbitals  
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conformational isomers   stereoisomer that can rotate about a single bond  
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electrophile   e- pair acceptor, lewis acid  
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nucleophile   e- pair donor  
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dipole-dipole   between polar molecules, larger dipoles cause higher B.P.  
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london dispersion   between nonpolar molecules, branching lowers B.P.  
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hydrogen bonding   strong dipole-dipole attraction, must have N-H or O-H  
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Arrhenius acids & bases   acids dissociate in water to give H3O+ ions bases dissociate in water to give OH- ions  
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Bronsted-Lowry acids & bases   acids = any species that can donate a proton bases = any species that can accept a proton  
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conjugate acid-base pairs   acids = plus one H base = minus one H  
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pKa   larger pKa = weaker acids, smaller pKa = stronger acids  
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electronegativity   increases going down the periodic table  
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size   size increases, acidity increases  
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hybridization effects on acidity   sp = small pKa, sp3 = large pKa  
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Lewis acids & bases   bases = nucleophiles (donate e-) acids = electrophiles (accept e-)  
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alcohol   R-OH  
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ether   R-O-R'  
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aldehyde   RCHO  
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ketone   RCOR'  
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carboxylic acids   -COOH  
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amines   RNH2 RNHR' R3N  
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amides   RCONH2 RCONHR RCONR2  
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nitrile   RCN  
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ester   RCOOR'  
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alkane formula   CnH2n+2  
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IUPAC rules - alkanes   longest chain with most substituents, alphabetical (ignoring prefixes), number starting with end closest to substituent  
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cycloalkane formula   CnH2n  
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cyclohexane stability   big groups more stable on equatorial (put smaller groups on axial if trans)  
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disubstituted cyclohexanes   Positions - cis - trans 1,2 - (a,e) or (e,a) - (a,a) or (e,e) 1,3 - (a,a) or (e,e) - (a,e) or (e,a) 1,4 - (a,e) or (e,a) - (a,a) or (e,e)  
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Chirality   -right gloves doesn't fit left hand -mirror images object is different from original object -cis isomer is achiral -trans is chiral  
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enantiomers   nonsuperimposable mirror images, different molecules -if there is only one chiral carbon in a molecule, its mirror image will be a different compound (enantiomer)  
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chiral carbons   tetrahedral carbons with four different groups attached, sp3  
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mirror planes of symmetry   molecule w/ internal plane of symmetry cannot be chiral  
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Cahn-Ingold-Prelog Rules   atom with highest atomic number is #1, double and triple bonds are treated like bonds to duplicate atoms  
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Assign R or S   lowest priority in back clockwise = R counterclockwise = S  
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specific rotation   [a]=a(observed)/c x l  
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optical purity   enantiomeric excess = observed specific rotation/specific rotation of pure enantiomer  
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allenes   chiral compounds with no chiral carbons contains sp carbon w/ adjacent double bonds -C=C=C- end carbons must have different groups  
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fischer projections   chiral carbon at intersection of horizontal and vertical lines horizontal lines are forward, vertical lines are behind the plane  
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fischer rules   carbon chain on vertical line highest oxidized carbon on top do not rotate 90 degrees  
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fischer R and S   lowest priority comes foward clockwise is S, counterclockwise is R *opposite assignment rules*  
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diastereomers   stereoisomers that are not mirror images cis-trans isomers molecules with 2 or more chiral carbons  
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alkenes   cis-trans isomers are not mirror images, so they are diastereomers  
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meso   have internal mirror plane maximum # is 2^n, n = # of chiral carbons  
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