Help
Options
Didn't know it?
click below
click below
Knew it?
click below
click below
Don't Know
Remaining cards (0)
Know
retry
shuffle
restart
0:00
Embed Code - If you would like this activity on your web page, copy the script below and paste it into your web page.
Normal Size Small Size show me how
Normal Size Small Size show me how
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) | acetaldehyde + ammonium chloride = imine; then add KCN to make a mixture of L + D amino acid |
| 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 is major product |
| thermodynamic product | lowest energy; most stable; slower formation path; favorable at high temps; more substituted is major product |
| acetal | from aldehydes; OR-OR |
| hemiacetal | from aldehydes; OR-OH bonded to same carbon; makes something a reducing sugar if present |
| ketal | from ketones; OR-OR |
| hemiketal | from ketones; OR-OH bonded to same carbon |
| 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 will 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/ether 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 |
| retro aldol rxn | heat + aqueous base turns aldol condensation product into an aldehyde and ketone |
| 2-chloro-2-methylpropane | tert-butyl chloride |
| aldose sugars | anomeric carbon has OH attached to it |
| ketose sugars | anomeric carbon has OH and CH2OH attached to it |
| 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 |
| anti-aromatic compounds | 4n electrons |
| azimuthal quantum number | "ℓ"; describes geometric shape (dumbell, sphere, etc.); values are from 0 to n-1 |
| magnetic quantum number | "(mℓ)"; describes orientation of orbitals in space; values are from -ℓ to +ℓ |
| amide synthesis | nucleophilic substitution of carb acid derivative with amine |
| carb acid derivative reactivity | amide -> carb acid -> ester -> acid anhydride -> acyl chloride |
| UV-vis spectroscopy | detects conjugated pi systems + presence of metal complexes |
| amide splitting | 5-8.5ppm |
| carb acid splitting | 10-12ppm |
| 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 |
Created by:
reynangu