mcat orgo
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| nucleophilic acyl substitution | addition at carbonyl carbon; removal of leaving group
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| ortho | 1,2 position
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| intramolecular bond | decreases bp because prevents inTERmolecular bonding from occuring
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| intermolecular bond | increase bp
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| para | 1,4 position
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| anisotropic effect | protons directly attached to aromatic rings have larger chemical shift
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| HOMO LUMO | smaller for conjugated/aromatic molecules; larger for nonconjugated/anti aromatic molecules
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| higher conjugation | higher wavelength absorption; reflects blue
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| lower conjugation | lower wavelength absorption; reflects red
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| mass spectrometry | tallest peak = most abundant ion; peak at largest value = molecular ion; (M-15 peak = loss of methy group)
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| steroids | nonhydrolyzable lipids; 4 fused rings
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| gabriel synthesis | potassium phthalimide + diethyl bromomalonate + alkyl halide = amino acid (mixture of enantiomers)
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| L configuration | highest # chiral carbon has S configuration; hydrogen drawn as dash
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| D configuration | highest # chiral carbon has R configuration; hydrogen drawn as solid wedge
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| sn2 | strong nucleophiles + polar aprotic solvent (DMSO, acetone); stereochem inversion at the carbon that is attacked
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| sn1 | weak nucleophile + polar protic solvent (water, alcohol)
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| aliphatic protons | attached to carbon atoms on a straight/branched structure, 1-2ppm
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| NaBH4 | weak reducing agent; selective to ketones
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| simple distillation | used when boiling points are under 150°C and at least 25°C apart
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| fractional distillation | used when boiling points are less than 25°C apart; molecule with lowest boiling point goes fastest and is in initial distillate
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| vacuum distillation | used when boiling points are more than 150°C; performed under reduced pressure, which lowers molecule's bp
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| liquid liquid extraction | organic layer = polar; aqueous layer = nonpolar
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| HPLC | nonpolar mobile phase, polar stationary phase; most polar elutes last (longer retention time) b/c it's attracted to stationary phase; for small sample sizes; mobile phase under pressure
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| imine formation (strecker synthesis) | acetaldehyde + ammonium chloride = imine; then add KCN to make a mixture of L + D amino acid
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| TLC chromatography | stationary phase = polar (travels less); mobile phase = nonpolar (travels more)
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| aldehydes + ketones | have lower bp than alcohol b/c cannot form H bonds w/ each other
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| kinetic product | highest energy; least stable; fast formation path; favorable at low temps; less substituted is major product
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| thermodynamic product | lowest energy; most stable; slower formation path; favorable at high temps; more substituted is major product
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| acetal | from aldehydes; OR-OR
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| hemiacetal | from aldehydes; OR-OH bonded to same carbon; makes something a reducing sugar if present
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| ketal | from ketones; OR-OR
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| hemiketal | from ketones; OR-OH bonded to same carbon
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| ring strain | higher for smaller rings b/c of crowding = larger wavelength # in IR
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| anhydride | cleaved to make ester + carb acid
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| rate limiting step | slowest; highest activation energy; smaller K constant
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| enantiomer | mirror image; not superimposable
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| diastereomer | not mirror image; not superimposable
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| pyranose | 6 membered sugar with oxygen in the ring
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| eclipse conformation | least stable; atoms stacked on top of each other
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| staggered conformation | most stable; atoms 60° apart
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| lactonization | intramolecular carb acid and alcohol cyclize to make cyclic ester
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| lactamization | intramolecular carb acid and amine and cyclize to make cyclic amide
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| long carbon chain | increases bp
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| short carbon chain | decreases bp
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| sucrose | glucose + fructose
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| lactose | glucose + galactose
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| maltose | glucose + glucose
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| furanose | 5 membered sugar with oxygen in the ring
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| fructose | ketohexose
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| glucose | aldohexose
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| galactose | aldohexose
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| ribose | aldopentose
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| tollens test | distinguishes reducing sugars, and aldehydes from ketones bc aldehydes will be oxidized to carb acids
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| boiling pt increasing order | alkanes -> ester -> ketones/aldehydes -> alcohols -> carb acids
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| NaH | weak base; forms thermodynamic enolate (most substituted) by deprotonating most substituted alpha carbon
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| LDA, -78 | strong base; forms kinetic enolate (less substituted)
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| M:M+2 ratio | 3:1 for bromine; 1:1 for chlorine
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| ester formation | alcohol + carb acid; uses acid catalyst + heat
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| anhydride formation | condensation of 2 carb acids OR carb acid + acid chloride
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| KmNO4 | strong oxidizing agent; primary alcohols and aldehydes -> carb acids; secondary alcohol -> ketone
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| D sugar (right) | highest # stereocenter is R
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| L sugar (left) | highest # stereocenter is S
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| gas chromatography | liquid stationary phase + gas mobile phase; higher bp travel slower (elutes last); lower bp travel faster (elutes first); column is heated
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| specific rotation | observed rotation/ (length in dm*conc.)
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| aromatic proton splitting | 6-8.5ppm
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| ch2 splitting | 4.5-5ppm
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| hydroxyl/ether splitting | 1-4ppm
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| 1°, 2°, 3° alkyl hydrogens | 1-2ppm
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| rotatable bonds | single bond, not connected to terminal atom
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| size-exclusion chromatography | large molecules elute first; small molecules elute last bc they get stuck in the small pores of the beads
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| right side of line structure | down on ring structrue
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| left side of line structure | up on ring structure
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| circular dichroism | assesses secondary + tertiary structures (a-helices/B-sheets) by measuring diff. in polarize light absorption
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| reducing sugar | monosaccharides w/ free hydroxyl on the end that can be oxidized
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| branching effect on bp | decreases bp b/c more surface area = less intermolecular interactions
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| wax is made up of | long chain FA + long chain alcohol connected by ester linkage
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| degrees of unsaturation | C - H/2 + N/2 + X/2 + 1
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| hell-volhard zelinksy rxn | PBr3, Br2, then H2O to brominate alpha-carbon on the carb acid
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| leaving group strength | NH2- < OH- < F- < Cl- < H2O < Br- < I-
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| regioselective | reaction occurs at one location over the other
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| stereoselective | one stereoisomer is preferred over the other
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| epimer | different spatial orientation at only 1 chiral center
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| retro aldol rxn | heat + aqueous base turns aldol condensation product into an aldehyde and ketone
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| 2-chloro-2-methylpropane | tert-butyl chloride
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| aldose sugars | anomeric carbon has OH attached to it
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| ketose sugars | anomeric carbon has OH and CH2OH attached to it
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| aromatic compounds | 4n + 2 electrons; if a seemingly sp3 molecule can donate e- to the ring and make it aromatic, then it acts as sp2 instead
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| anti-aromatic compounds | 4n electrons
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| azimuthal quantum number | "ℓ"; describes geometric shape (dumbell, sphere, etc.); values are from 0 to n-1
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| magnetic quantum number | "(mℓ)"; describes orientation of orbitals in space; values are from -ℓ to +ℓ
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| amide synthesis | nucleophilic substitution of carb acid derivative with amine
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| carb acid derivative reactivity | amide -> carb acid -> ester -> acid anhydride -> acyl chloride
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| UV-vis spectroscopy | detects conjugated pi systems + presence of metal complexes
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| amide splitting | 5-8.5ppm
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| carb acid splitting | 10-12ppm
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| claisen condensation | alpha carbon deprotonated to make enolate anion
enolate anion attacks carbonyl carbon of another ester
alkoxy group eliminated to form beta-keto-ester
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| fractional crystillization | separates molecules based on solubility; least soluble crystallizes first
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| horizontal line on fischer projection | wedge (pointing front)
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| vertical line on fischer projection | dash (pointing back)
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| meso compound | achiral, has multiple chiral centers, and doesn't rotate polarized light b/c of internal symmetry
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