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The Language of Organic Chemistry

To refresh your memory of more than 90 words and phrases commonly used in Organic Chemistry.

Lewis acidlikes lone pairs
Lucas reagentconverts tertiary alcohols to alkyl chlorides
Tollens reagentoxidizes aldehydes
Friedel-Craft alkylationadds alkyl groups to aromatics
Friedel-Craft acylationadds acyl groups to aromatics
Jones reagentsame as chromic acid
Collins reagentoxidizes alcohols to aldehydes or ketones
Fischer esterificationacid-catalyzed reaction of acids and alcohols
Grignard reagentan organometallic made from Mg
Williamson synthesismakes ethers from alkoxides
wavenumberinverse wavelength
fingerprint regionIR region below about 1500 wavenumbers
triple-bond regionIR region at 2300-2100 wavenumbers
double-bond regionIR region at 1800-1600 wavenumbers
X-H regionIR region at 2850-3500 wavenumbers
downfieldto higher chemical shift values
upfieldto lower chemical shift values
shieldingcausing a shift to higher fields
deshieldingcausing a shift to lower fields
multiplicitythe splitting of a signal
Pascal's triangletool to predict peak heights for split signals
coupling constantamount of signal splitting in Hz
accidental overlapwhen two or more signals have very close chemical shifts
broad band decouplingmakes all carbon signals singlets
off-resonance decouplingleaves carbon signals as multiplets
halohydrina 2-haloalcohol
Huckel's rule4n+2 electrons in a flat, cyclic and contiguous pi system
arenegeneric name for an aromatic
heteroaromaticaromatic containing elements other than carbon
annulenegeneric name for an aromatic hydrocarbon ring
polynuclear aromatic hydrocarbon (PAH)contains fused hydrocarbon aromatic rings
Clemmensen reductionuses Zn amalgam in acid
activating groupgroup that adds electron density to an aromatic ring
deactivating groupgroup that removes electron density from an aromatic ring
benzylic positionthe position on an alkyl chain next to an aromatic ring
hemiacetalfunctionality with one hydroxyl and one alkoxy group attached to the same carbon
hydrazonecondensation product from a hydrazine and a ketone or aldehyde
oximecondensation product from hydroxylamine and a ketone or aldehyde
quaternary ammonium ionan amine derivative with four alkyl or aryl substituents
N-alkylationreaction of an amine with an alkyl halide or tosylate
N-acylationreaction of an amine with an acid chloride
fatty acidlong-chain carboxylic acid
carboxylationadding carbon dioxide (to a Grignard)
acid anhydridecondensation product from two carboxylic acids
lactonea cyclic ester
lactama cyclic amide
terminal alkynea singly-substituted alkyne
internal alkyneshows up weakly in IR
hydrolysiscleavage with water
acetylide iona deprotonated terminal alkyne
acylium ionreactive entity during Friedel-Craft acylation
fuming sulfuric acidsulfuric acid containing sulfur trioxide
solvationthe ability to interact with solutes
secondary amidean amide with one other N-substituent
iminium ioncondensation product from a secondary amine with an aldehyde or ketone
Lindlar's catalystPd on barium sulfate poisoned with quinoline
Fischer projectiona way to draw molecules to compare and assign stereoisomers
Newman projectiona way to draw molecules by looking down a bond axis
Hammond Postulatethe structure of a transition state resembles that of the closest stable structure
mesoachiral though it contains chiral centres
boat forman unstable conformation in cyclohexanes
chair forma stable conformation in cyclohexanes
enantiomerspaired isomers that differ only in handedness
diastereomersstereoisomers that are not enantiomers
Saytzeff rulemost substituted alkene prefered
Markovnikoff additionvia the most stable carbocation intermediate
Walden inversionsubstitution that inverts the configuration of a chiral carbon
vicinalone neighbouring carbons
geminalon the same carbon
sigma complexintermediate of electrophilic aromatic substitution
pi systemoverlapping p orbitals
racemic mixturean equal mix of enantiomers
phenolaromatic alcohol
spectraplural of spectrum
cyano groupfound in nitriles
hydrogenationadding the elements of hydrogen
endothermictaking up heat
exothermicgiving off heat
eclipsed conformationhigh-energy conformation in ethane fragments
staggered conformationlow-energy conformation in ethane fragments
diboranedimer of borane
dextrorotatoryturning the plane of polarized light to the right
levorotatoryturning the plane of polarized light to the left
chloronium ionintermediate in addition to chlorine to alkenes
Cahn-Ingold-Prelog conventionset of rules for assigning absolute configuration
arylgeneric name for an aromatic substituent
tertiary aminehas three substituents
primary amidemay give two spikes near 3300 wavenumbers
Lindlar's catalystgives cis-alkenes from alkynes
bromonium ionintermediate during addition of bromine to alkenes
acetalhas 2 alkoxy groups on the same carbon
conjugationalignment of a p orbital with a pi system
trans-diaxialconformation of an E2 transition state

Pierre Potvin

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