Organic Chemistry Flashcards
name the number of carbons for a molecule going from 1C to 12C
methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decade, undecane, dodecane
geminal vs vicinal diols
geminal are 2 hydroxyl groups on the same C, vicinal are 2 hydroxyl groups on adjacent C’s
what are the common names for methanal, ethanal, propanal, and propanone, respectively?
formaldehyde, acetaldehyde, propionaldehyde, acetone
what are the common names for methanoic acid, ethanoic acid, propanoic acid?
formic acid, acetic acid, propionic acid
how do you name an ester?
first term is alkyl name of esterifying group (opposite from carbonyl) and second term is name of the parent acid (ENDING IN -OATE not -OIC ACID)
how to name an amide?
“N-“ before any group on the Nitrogen, and suffix changes to -amide
diff. b/w structural isomers and stereoisomers? conformational and configurational isomers?
structural has diff. connectivity while stereoisomers have the same; conformational differ in rotation around a single (sigma) bonds, while configurational can be interconverted ONLY BY BREAKING BONDS
what is n? what is l? what is mL? what is ms?
- n is principal quantum # and is the energy level of e-, basically its saying the size of the atom
- l is azimuthal quantum #, ranging from 0 to n-1; basically it describes sub shells (s,p,d,f = 0,1,2,3)
- mL describes orbitals, ranging from -l to +l
- ms is spin quantum #, +/- 1/2
bonding vs. anti bonding
pi vs. sigma bonds
what is sp3? sp2? sp?
bonding is when signs of wave functions are the same (+ and + or - and -); anti bonding is when they’re opp.
sigma is a single bond, pi bonds are when pi orbitals line up and overlap
sp3 is single bond, sp2 is double, sp is triple
how does nucleophilicity change with:
- charge
- EN
- steric hindrance
- solvent (how do protic solvents affect nucleophilicity)
- charge - increases w/ more negative charge
- EN - decreases w/ increasing EN
- steric hindrance - decreases w/ more hindrance
- solvent - protic solvents hinder nucleophilicity
what are some good reagents in oxidation reactions? what happens in this reaction (generally)
reduction reactions? what happens in this reaction (generally)
how do you name multiple substituents on a benzene?
PCC, CrO3/pyridine, H2CrO4, KMnO4, H2O2, O3, mCPBA, NaIO4 (metals w/ a lot of oxygen)
- increased bonds to oxygen
NaH, CaH2, LiAlH4, NaBH4 (metals w/ a lot of hydrogen)
- increased bonds to hydrogen
o / ortho (1 spot over); m / meta (2 spots over); p / para (3 spots over)
what do mesylates (methylsplfonyl chloride) and tosylates (toluenesulfonic acid) do?
how else can you protect groups?
make OH a good LG; also protect OH to it doesn’t react
using acetals (for primary carbons) or ketals (secondary carbons)
what is a quinone? how do you get it?
describe a hemiacetal and hemiketal, what about acetal and ketal
conjugated (resonance stabilized) ring structure that’s not necessarily aromatic
- react w/ oxidizing agents
occurs from alcohol reacts w/ aldehyde and ketone, respectively
- hemiacetal is R, H, OR, OH and hemiketal is R, R, OR, OH
occurs from reacting another alcohol w/ hemiacetal or hemiketal
- acetal is R H OR OR and ketal is R R OR OR
what is an imine? what can it be tautomerized into?
what is a cyanohydrin?
what is an aldol?
a nitrogen double bonded to a carbon; enamine (double bond AND nitrogen containing group)
- CONDENSATION RXN
R R OH CN
- formed by reacting HCN w/ ketone or aldehyde
compound that has alcohol and aldehyde
what is an enol / enolate? how do you get them?
what is preferred? enol or keto form?
what enolate (more or less sub) will form if a ketone has diff alkyl groups?
enol is double bond and alcohol, enolate is double bond and O-
- get enol by reacting ketone w/ acid, and enolate by reacting ketone w/ base
KETO FORM
MORE SUBSTITUTED ALKENE
what is a cyclic amide called? cyclic esters?
what do you react to get an amide? ester? anhydride?
- what kind of rxn is it for all of them?
rank the following in order of decreasing reactivity
- amide
- anhydride
- carboxylic acid
- ester
what is a transesterification?
lactams; lactones
amine & carboxylic acid; alcohol & carboxylic acid; two carboxylic acids
- condensation (2 molecules to 1 and loss of water)
anhydride > ester = carboxylic acid > amide
transesterification is when an ester and an alcohol switch alkyl groups
what is strecker synthesis? what rxn types?
gabriel synthesis? what rxn types?
aldehyde + NH4Cl + KCN + H2O -> amino acid
- condensation, nuc. addition, hydrolysis
potassium phthalimide + diethyl bromomalonate + alkyl halide + H2O -> amino acid
- two SN2 rxns, hydrolysis, decarboxylation
what does IR spec measure?
what are the absorption peaks for O-H, N-H, and C=O?
what is UV spec and what is it best for?
measures molecular vibrations; plotted as % transmittance (amount of light passing through sample reaching detector vs. wavenumber)
- O-H is broad around 3300 cm^-1
- N-H is sharp around 3300 cm^-1
- C=H is sharp around 1750 cm^-1
pass UV light through sample and record absorbance, telling us extent of conjugation
- most useful for compounds containing double bonds or heteroatom w/ long pairs that create conjugated systems
what is NMR? how does it work?
what is the n+1 rule?
what are the main shifts for
- alkyl groups
- alkynes
- alkenes
- aromatics
- aldehydes
- carboxylic acids
NMR measures alignment of nuclear spin w/ applied magnetic field; determines structure (connectivity) of compound, including functional groups
- nuclei are in alpha (lower energy) state or beta (higher energy) state; radiofrequency pulses push nucleus from alpha to beta state and these frequencies can be measured
if a proton has n protons that are three bonds away, it will be split into n+1 peaks (NOT H’s ATTACHED TO O OR N)
- alkyl groups - 0-3 ppm
- alkynes - 2-3 ppm
- alkenes - 4.6-6 ppm
- aromatics - 6-8.5 ppm
- aldehydes - 9-10 ppm
- carboxylic acids - 10.5-12 ppm
what is extraction? explain ‘like dissolves like’
what is filtration? differentiate b/w gravity and vacuum filtration
explain recrystallization
transfer of a dissolved compound (desired product) from starting solvent into solvent in which product is more soluble
- like dissolves like means that polar substances associate w/ other polar substances, and non polar with other non polar
filtration slates a solid (residue) from a liquid (leftover liquid is filtrate)
- gravity filtration is when desired product is in filtrate, vacuum filtration is when solid is product
recrystallization is used to further purify crystals, by dissolving product in minimal hot solvent and recrystallizing as it cools
what is distillation?
when is fractional distillation used? vacuum distillation?
distillation is for when product is also liquid and soluble in solvent, so take advantage of diff. BP’s. (liquid w/ lower BP rises first, condenses in distillation column (condensate), and drips down and becomes distillate (end product).
fractional is used when BP’s are within 25 degrees C, vacuum is when BP is over 150 degrees C
what is chromatography used for?
describe TLC/ paper chromatography (also what is reverse phase chromatography)
describe retardation factor (Rf)
separates compounds based on how strongly they adhere to the solid (stationary phase)
TLC uses silica gel, paper uses paper (cellulose)
- sample we want to separate is placed onto adsorbent (spotting), plate is placed upright in eluent, and solvent moves up
- POLAR COMPOUNDS MOVE SLOWER
- reverse phase is when polar compounds move faster
Rf is distance spot moved/distance solvent front moved, so the larger the number, the further is moved
describe column chromatography
describe ion exchange chromatography
describe size exclusion chromatography
uses column filled w/ silica beads as adsorbent (more similar sample is to stationary phase, slower elution time) (can be used for macromolecules too)
beads in column are coated w/ charged substance, so they attract opp. charged compounds; lastly eluted w/ salt compound
beads contain tiny pores, so smaller compounds get stuck in those and larger ones elute first
describe affinity chromatography
describe gas chromatography (GC) aka vapor phase chromatography (VPC)
what is high performance liquid chromatography (HPLC)
protein of interest is bound by creating column w/ high affinity for that protein (ex. coating beads with receptor that binds protein or antibody), then eluted
eluent is gas not liquid, and run through column containing adsorbent
eluent is liquid and travels through column of denied composition, uses liquid under pressure (computer control)
