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77 Cards in this Set

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SN2
Primary substrate (steric hindrance), no rearrangement, polar aprotic solvent ( no H bonding), complete stereo inversion, reaction rate = k [Nuc][Elect]
SN1 substrate
tertiary
SN1 rearrangementss
possible, from less stable to more stable
SN1 solvent
polar protic (H bonding) to stabilize carbocation
Stereochemistry SN1
racemic mixture
SN1 rate law
rate = k [electrophile]
Dehydration of alcohols
alcohol -> alkene, favored by strong H+ and high T, possible rearrangements
Formation of haloalkanes
alcohol + PBr3
alcohol + SOCl2
E1 substrate
tertiary
E1 solvent
protic, H bonding to stabilize carbocation
E1 product
major - more substituted alkene
E1 rate law
rate = k[haloalkane]
E1 conditions
high T, strong base
E2 substrate
tertiary
E2 solvent
polar aprotic, no H bonding
E2 stereochemistry
anti of proton and leaving group
E2 rate law
rate = k [base][haloalkane]
HX additon to alkenes
Markovnikov addition, racemic mixture, possible rearrangements
HBr + peroxides addition
no rearrangements , anti markovnikov, only for HBr
Oxymercuration-Demercuration
alkene - alcohol, Markovnikov addition, no rearrangement
Hydroboration oxidation
anti Markovnikov alcohol, BH3/H2O2, OH on less substituted carbon
Hydrogenation of alkenes
syn addition, only in the presence of catalyst
Hydrogenation of alkynes with Lindlar catatlyst
stops at alkene , syn addition
Hydrogenation of alkynes with Na/NH3
stops at alkene, trans addition
Addition of X2 to alkenes
intermediate halonium ion, positive charge on bridged halogen, anti addition, no rearrangements
Epoxide formation
alkene + peroxy acid = epoxide + carboxylic acid
Epoxide hydrolysis results in
trans diol
In order to form cis diol need to react alkene with
KMnO4 or OsO4
Ozonolysis results in cleavage of double bond and formation of
aldehydes and ketones
Criteria for aromaticity
1.cyclic system with unhybridized p orbitals
2.flat and planar
3.4n+2 e's
Ortho para directors
activating groups - NR2, OH, OR, amides, esters, R groups

Cl, Br, I deactivators but ortho para
Meta directing
e-n withdraawing groups
NR3, NO2, cyanide, ketones, carbox acids etc
Acetal formation
ketone + HCl/ROH - hemiacetal
hemiacetal + ROH (-H2O) - Acetal
Extraction
technique that allows separation of a substance from a mixture of substancesby adding a solvent that the compound of interest s highly soluble in
Crystallization
method of separation that relies on differential solubilities of two compounds in given solvent
Thin layer chromatography
compounds separated based on polarity
Polar components move slower or faster?
move slower since interact with polar stationary phase
calculating R for TLC
R = distance traveled/distance to solvent front
Gas chromatography
separation technique based on ifferent volatility
Rates of movement in GC
more volatile faster, less volatile slower
Simple distillation
when trace impurities need to be removed from relatively pure compound or in a mixture with significantly different boiling points
Fractional distillation
small difference in boiling points
IR of alkenes
double bond stretch at 1650 cm
IR carbonyl
1700
IR alkynes
2600
IR nitriles
2100
IR OH
36000
CH stretch
3000-3300
What can be seen from NMR
1.# of sets of peaks = # different H's
2. chemical shift - chemical environment
3.integration # - # of Hs in the set
4.splitting pattern - neighbours
If protons near electronegative group - downfield or upfield?
downfield and deshielded
WHich amino acid is not chiral?
glycine
All animal amino acids have... configuration
L, amino group on the left
All carbohydrates have ... configuration
D
Amino acid is
a. basic
b. acidic
c. both
c, amphoteric
Hydrophobic amino acids
either aliphatic or aromatic side chains
Amino acid with aliphatic side chains
glycine, alanine, valine, leucine, isoleucine
Amino acids with aromatic side chains
phenylalanine, tyrosine, tryptophan
Hydrophilic amino acids
acidic, basic and uncharged
Acidic hydrophilic amino acids
glutamic and aspartic amino acids
Basic hydrophlic amino acids
lysine, arginine and histidine
Histidine - proton acceptor or donor?
both, His goes both ways
uncharged polar amino acids
serie, threonine, asparagine, glutamine
Sulfur containing amino acids
methionine, cysteine
Denaturation
disruption of proteins shape w/out breaking peptide bonds
Proteins can be denatured by
urea, extremes of pH, extremes of temp, changes in salt concentration
Primary structure
amino acid sequence, determined by peptide bond
Secondary structure
hydrogen bonds between backbone groups
Tertiary structure
Hydrophobic/hydrophilic interactions
Quaternary structure
Various bonds between separate chains
Formula of carbohydrate
CnH2nOn
What gives positive Benedicts test?
aldehydes, ketones, hemiacetals
What gives negative Benedicts test?
acetals
Soaps
sodium salts of fatty acids
amphipathic, both hydrophilic and hydrophobic
Fatty acids
stored as fat, fat- triacylglycerol
Triglyceride
three fatty acids esterified to a glycerol
Glycerol
three hydroxyl groups can be esterified to fatty acids
Saponification
Triacylglycerol + NaOH ->>glycerol + 3 fatty acids