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Ch. 1-5

CHEM 301

TermDefinition
constitutional/structural isomers differ in their bonding sequence
stereoisomers differ only in the arrangement of the atoms in space
cis-trans isomers cis = same side, trans = opposite side *there must be 2 different groups on the sp2 carbon
pauli exculsion principle each orbital may hold a max. of 2 e- w/ opposite spins
hund's rule equal energy orbitals are half-filled, the fully filled
aufbau principle filling up the energy level diagram one e- at a time, lower energy orbitals are filled before higher energy orbitals
conformational isomers stereoisomer that can rotate about a single bond
electrophile e- pair acceptor, lewis acid
nucleophile e- pair donor
dipole-dipole between polar molecules, larger dipoles cause higher B.P.
london dispersion between nonpolar molecules, branching lowers B.P.
hydrogen bonding strong dipole-dipole attraction, must have N-H or O-H
Arrhenius acids & bases acids dissociate in water to give H3O+ ions bases dissociate in water to give OH- ions
Bronsted-Lowry acids & bases acids = any species that can donate a proton bases = any species that can accept a proton
conjugate acid-base pairs acids = plus one H base = minus one H
pKa larger pKa = weaker acids, smaller pKa = stronger acids
electronegativity increases going down the periodic table
size size increases, acidity increases
hybridization effects on acidity sp = small pKa, sp3 = large pKa
Lewis acids & bases bases = nucleophiles (donate e-) acids = electrophiles (accept e-)
alcohol R-OH
ether R-O-R'
aldehyde RCHO
ketone RCOR'
carboxylic acids -COOH
amines RNH2 RNHR' R3N
amides RCONH2 RCONHR RCONR2
nitrile RCN
ester RCOOR'
alkane formula CnH2n+2
IUPAC rules - alkanes longest chain with most substituents, alphabetical (ignoring prefixes), number starting with end closest to substituent
cycloalkane formula CnH2n
cyclohexane stability big groups more stable on equatorial (put smaller groups on axial if trans)
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)
Chirality -right gloves doesn't fit left hand -mirror images object is different from original object -cis isomer is achiral -trans is chiral
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)
chiral carbons tetrahedral carbons with four different groups attached, sp3
mirror planes of symmetry molecule w/ internal plane of symmetry cannot be chiral
Cahn-Ingold-Prelog Rules atom with highest atomic number is #1, double and triple bonds are treated like bonds to duplicate atoms
Assign R or S lowest priority in back clockwise = R counterclockwise = S
specific rotation [a]=a(observed)/c x l
optical purity enantiomeric excess = observed specific rotation/specific rotation of pure enantiomer
allenes chiral compounds with no chiral carbons contains sp carbon w/ adjacent double bonds -C=C=C- end carbons must have different groups
fischer projections chiral carbon at intersection of horizontal and vertical lines horizontal lines are forward, vertical lines are behind the plane
fischer rules carbon chain on vertical line highest oxidized carbon on top do not rotate 90 degrees
fischer R and S lowest priority comes foward clockwise is S, counterclockwise is R *opposite assignment rules*
diastereomers stereoisomers that are not mirror images cis-trans isomers molecules with 2 or more chiral carbons
alkenes cis-trans isomers are not mirror images, so they are diastereomers
meso have internal mirror plane maximum # is 2^n, n = # of chiral carbons
Created by: slb23310