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77 Cards in this Set
- Front
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SN2
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Primary substrate (steric hindrance), no rearrangement, polar aprotic solvent ( no H bonding), complete stereo inversion, reaction rate = k [Nuc][Elect]
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SN1 substrate
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tertiary
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SN1 rearrangementss
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possible, from less stable to more stable
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SN1 solvent
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polar protic (H bonding) to stabilize carbocation
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Stereochemistry SN1
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racemic mixture
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SN1 rate law
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rate = k [electrophile]
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Dehydration of alcohols
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alcohol -> alkene, favored by strong H+ and high T, possible rearrangements
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Formation of haloalkanes
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alcohol + PBr3
alcohol + SOCl2 |
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E1 substrate
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tertiary
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E1 solvent
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protic, H bonding to stabilize carbocation
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E1 product
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major - more substituted alkene
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E1 rate law
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rate = k[haloalkane]
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E1 conditions
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high T, strong base
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E2 substrate
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tertiary
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E2 solvent
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polar aprotic, no H bonding
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E2 stereochemistry
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anti of proton and leaving group
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E2 rate law
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rate = k [base][haloalkane]
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HX additon to alkenes
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Markovnikov addition, racemic mixture, possible rearrangements
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HBr + peroxides addition
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no rearrangements , anti markovnikov, only for HBr
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Oxymercuration-Demercuration
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alkene - alcohol, Markovnikov addition, no rearrangement
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Hydroboration oxidation
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anti Markovnikov alcohol, BH3/H2O2, OH on less substituted carbon
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Hydrogenation of alkenes
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syn addition, only in the presence of catalyst
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Hydrogenation of alkynes with Lindlar catatlyst
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stops at alkene , syn addition
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Hydrogenation of alkynes with Na/NH3
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stops at alkene, trans addition
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Addition of X2 to alkenes
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intermediate halonium ion, positive charge on bridged halogen, anti addition, no rearrangements
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Epoxide formation
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alkene + peroxy acid = epoxide + carboxylic acid
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Epoxide hydrolysis results in
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trans diol
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In order to form cis diol need to react alkene with
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KMnO4 or OsO4
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Ozonolysis results in cleavage of double bond and formation of
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aldehydes and ketones
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Criteria for aromaticity
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1.cyclic system with unhybridized p orbitals
2.flat and planar 3.4n+2 e's |
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Ortho para directors
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activating groups - NR2, OH, OR, amides, esters, R groups
Cl, Br, I deactivators but ortho para |
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Meta directing
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e-n withdraawing groups
NR3, NO2, cyanide, ketones, carbox acids etc |
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Acetal formation
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ketone + HCl/ROH - hemiacetal
hemiacetal + ROH (-H2O) - Acetal |
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Extraction
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technique that allows separation of a substance from a mixture of substancesby adding a solvent that the compound of interest s highly soluble in
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Crystallization
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method of separation that relies on differential solubilities of two compounds in given solvent
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Thin layer chromatography
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compounds separated based on polarity
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Polar components move slower or faster?
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move slower since interact with polar stationary phase
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calculating R for TLC
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R = distance traveled/distance to solvent front
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Gas chromatography
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separation technique based on ifferent volatility
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Rates of movement in GC
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more volatile faster, less volatile slower
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Simple distillation
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when trace impurities need to be removed from relatively pure compound or in a mixture with significantly different boiling points
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Fractional distillation
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small difference in boiling points
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IR of alkenes
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double bond stretch at 1650 cm
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IR carbonyl
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1700
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IR alkynes
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2600
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IR nitriles
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2100
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IR OH
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36000
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CH stretch
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3000-3300
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What can be seen from NMR
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1.# of sets of peaks = # different H's
2. chemical shift - chemical environment 3.integration # - # of Hs in the set 4.splitting pattern - neighbours |
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If protons near electronegative group - downfield or upfield?
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downfield and deshielded
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WHich amino acid is not chiral?
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glycine
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All animal amino acids have... configuration
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L, amino group on the left
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All carbohydrates have ... configuration
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D
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Amino acid is
a. basic b. acidic c. both |
c, amphoteric
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Hydrophobic amino acids
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either aliphatic or aromatic side chains
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Amino acid with aliphatic side chains
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glycine, alanine, valine, leucine, isoleucine
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Amino acids with aromatic side chains
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phenylalanine, tyrosine, tryptophan
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Hydrophilic amino acids
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acidic, basic and uncharged
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Acidic hydrophilic amino acids
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glutamic and aspartic amino acids
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Basic hydrophlic amino acids
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lysine, arginine and histidine
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Histidine - proton acceptor or donor?
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both, His goes both ways
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uncharged polar amino acids
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serie, threonine, asparagine, glutamine
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Sulfur containing amino acids
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methionine, cysteine
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Denaturation
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disruption of proteins shape w/out breaking peptide bonds
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Proteins can be denatured by
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urea, extremes of pH, extremes of temp, changes in salt concentration
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Primary structure
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amino acid sequence, determined by peptide bond
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Secondary structure
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hydrogen bonds between backbone groups
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Tertiary structure
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Hydrophobic/hydrophilic interactions
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Quaternary structure
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Various bonds between separate chains
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Formula of carbohydrate
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CnH2nOn
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What gives positive Benedicts test?
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aldehydes, ketones, hemiacetals
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What gives negative Benedicts test?
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acetals
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Soaps
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sodium salts of fatty acids
amphipathic, both hydrophilic and hydrophobic |
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Fatty acids
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stored as fat, fat- triacylglycerol
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Triglyceride
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three fatty acids esterified to a glycerol
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Glycerol
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three hydroxyl groups can be esterified to fatty acids
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Saponification
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Triacylglycerol + NaOH ->>glycerol + 3 fatty acids
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