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nucleophilic acyl substitution
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mcat orgo
| Question | Answer |
|---|---|
| nucleophilic acyl substitution | addition at carbonyl carbon; removal of leaving group |
| ortho | 1,2 position |
| intramolecular bond | decreases bp because prevents inTERmolecular bonding from occuring |
| intermolecular bond | increase bp |
| para | 1,4 position |
| anisotropic effect | protons directly attached to aromatic rings have larger chemical shift |
| HOMO LUMO | smaller for conjugated/aromatic molecules; larger for nonconjugated/anti aromatic molecules |
| higher conjugation | higher wavelength absorption; reflects blue |
| lower conjugation | lower wavelength absorption; reflects red |
| mass spectrometry | tallest peak = most abundant ion; peak at largest value = molecular ion; (M-15 peak = loss of methy group) |
| steroids | nonhydrolyzable lipids; 4 fused rings |
| gabriel synthesis | potassium phthalimide + diethyl bromomalonate + alkyl halide = amino acid (mixture of enantiomers) |
| L configuration | highest # chiral carbon has S configuration; hydrogen drawn as dash |
| D configuration | highest # chiral carbon has R configuration; hydrogen drawn as solid wedge |
| sn2 | strong nucleophiles + polar aprotic solvent (DMSO, acetone); stereochem inversion at the carbon that is attacked |
| sn1 | weak nucleophile + polar protic solvent (water, alcohol) |
| aliphatic protons | attached to carbon atoms on a straight/branched structure, 1-2ppm |
| NaBH4 | weak reducing agent; selective to ketones |
| simple distillation | used when boiling points are under 150°C and at least 25°C apart |
| fractional distillation | used when boiling points are less than 25°C apart; molecule with lowest boiling point goes fastest and is in initial distillate |
| vacuum distillation | used when boiling points are more than 150°C; performed under reduced pressure, which lowers molecule's bp |
| liquid liquid extraction | organic layer = polar; aqueous layer = nonpolar |
| 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 |
| imine formation (strecker synthesis) | aldehyde + ammonia |
| TLC chromatography | stationary phase = polar (travels less); mobile phase = nonpolar (travels more) |
| aldehydes + ketones | have lower bp than alcohol b/c cannot form H bonds w/ each other |
| kinetic product | highest energy; least stable; fast formation path; favorable at low temps; less substituted |
| thermodynamic product | lowest energy; most stable; slower formation path; favorable at high temps; more substituted |
| acetal | from aldehydes; OR-OR |
| hemiacetal | from aldehydes; OR-OH |
| ketal | from ketones; OR-OR |
| hemiketal | from ketones; OR-OH |
| ring strain | higher for smaller rings b/c of crowding = larger wavelength # in IR |
| anhydride | cleaved to make ester + carb acid |
| rate limiting step | slowest; highest activation energy; smaller K constant |
| enantiomer | mirror image; not superimposable |
| diastereomer | not mirror image; not superimposable |
| pyranose | 6 membered sugar with oxygen in the ring |
| eclipse conformation | least stable; atoms stacked on top of each other |
| staggered conformation | most stable; atoms 60° apart |
| lactonization | intramolecular carb acid and alcohol cyclize to make cyclic ester |
| lactamization | intramolecular carb acid and amine and cyclize to make cyclic amide |
| long carbon chain | increases bp |
| short carbon chain | decreases bp |
| sucrose | glucose + fructose |
| lactose | glucose + galactose |
| maltose | glucose + glucose |
| furanose | 5 membered sugar with oxygen in the ring |
| fructose | ketohexose |
| glucose | aldohexose |
| galactose | aldohexose |
| ribose | aldopentose |
| tollens test | distinguishes reducing sugars, and aldehydes from ketones bc aldehydes can be oxidized to carb acids |
| boiling pt increasing order | alkanes -> ester -> ketones/aldehydes -> alcohols -> carb acids |
| NaH | weak base; forms thermodynamic enolate (most substituted) by deprotonating most substituted alpha carbon |
| LDA, -78 | strong base; forms kinetic enolate (less substituted) |
| M:M+2 ratio | 3:1 for bromine; 1:1 for chlorine |
| ester formation | alcohol + carb acid; uses acid catalyst + heat |
| anhydride formation | condensation of 2 carb acids OR carb acid + acid chloride |
| KmNO4 | strong oxidizing agent; primary alcohols and aldehydes -> carb acids; secondary alcohol -> ketone |
| D sugar (right) | highest # stereocenter is R |
| L sugar (left) | highest # stereocenter is S |
| gas chromatography | liquid stationary phase + gas mobile phase; higher bp travel slower (elutes last); lower bp travel faster (elutes first); column is heated |
| specific rotation | observed rotation/ (length in dm*conc.) |
| aromatic proton splitting | 6-8.5ppm |
| ch2 splitting | 4.5-5ppm |
| hydroxyl splitting | 1-4ppm |
| 1°, 2°, 3° alkyl hydrogens | 1-2ppm |
| rotatable bonds | single bond, not connected to terminal atom |
| size-exclusion chromatography | large molecules elute first; small molecules elute last bc they get stuck in the small pores of the beads |
| right side of line structure | down on ring structrue |
| left side of line structure | up on ring structure |
| circular dichroism | assesses secondary + tertiary structures (a-helices/B-sheets) by measuring diff. in polarize light absorption |
| reducing sugar | monosaccharides w/ free hydroxyl on the end that can be oxidized |
| branching effect on bp | decreases bp b/c more surface area = less intermolecular interactions |
| wax is made up of | long chain FA + long chain alcohol connected by ester linkage |
| degrees of unsaturation | C - H/2 + N/2 + X/2 + 1 |
| hell-volhard zelinksy rxn | PBr3, Br2, then H2O to brominate alpha-carbon on the carb acid |
| leaving group strength | NH2- < OH- < F- < Cl- < H2O < Br- < I- |
| regioselective | reaction occurs at one location over the other |
| stereoselective | one stereoisomer is preferred over the other |
| epimer | different spatial orientation at only 1 chiral center |
Created by:
reynangu