CHEM 301
Quiz yourself by thinking what should be in
each of the black spaces below before clicking
on it to display the answer.
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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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