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Verschiedene Reagenzien

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xixixi's version from 2016-09-24 20:26

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Question Answer
OsO4osmium tetroxide - blindingly good for dihydroxylation of alkenes, volatile, syn-Add
Pb(OAc)4lead tetraacetate - starkes Ox.M; tox.;; for cleavage of diols zu ald./ket; in Hofmann-Umlag statt Br2; Acetyloxy-Quelle; uvm
mCPBAmeta chloro perbenzoic acid - for epoxidations, and Baeyer villiger rxns of ketones
NaIO4sodium periodate - Starkes OxM.; tox; for cleavage of 1,2-diols to ald&ket; Lemieux-Johnson-Ox.
LDAlithium diisopropyl amide - strong base (useful for making enolates from carbonyl compounds)
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Question Answer
LiAlH4lithium aluminum hydride - strong reducing agent, alle DB außer C=C&alkin; C=O zu alk; N-Verb zu amin
NBSN-bromosuccinimide - brominating reagent.Oft Ersatz f. Br2; feststoff; Add. to alkenes, Allylic/benzylic bromination; prod mit delta od. hv konst. level an Br2; mit DBU: variante d. Hofmann-Umlag; Br = E+!!!
DCCN,N′-Dicyclohexylcarbodiimid- agent for peptide couplings (amine plus carboxylic acid). aktiviert Carbonyl-C für Nu-Angriff vom Amin; wird dabei zu harnstoffderivat; "dehydrating agent"
KMnO4postassium permanganate - can dihydroxylate alkenes (kalte, basiche Lsg); ox. cleavage of alkenes/alkynes; ox. of aromatic alkanes
NaBH4sodium borohydride - reducing agent - reduces aldehydes/ketones to alcohols; milder als LiAlH4
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BH3borane - Boran;for hydroboration of alkenes (gives anti-Markovnikoff alk-product) and alkynes (keton)
PCCpyridinium chlorochromate - milder version of chromic acid. oxidizes alc one rung up the oxidation ladder, from 1° alc to ald /from 2°alc to ket. Unlike chromic acid, PCC will not oxidize ald to carboxylic acids.
O3ozone, ersetzt DB, 3fachB und Azoverb. mit C=O to give aldehydes/ketones/acids (depends on workup of ozonide)
Hg(OAc)2Mercuric acetate - for oxymercuration of alkenes; gibt in Anw. v. Alk Ether, Hg wird dc NaBH4 entf
R2CuLiOrganocuprate or Gilman reagent - for 1,4-addition on a,B-unsaturated ket/ester/sren; SN2! C-C-Knüpfung!!
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SOCl2Thionyl chloride, for making acid or alkyl chlorides; nebenprod: SO2&HCl!
Pd/CPalladium on carbon, for hydrogenation of double bonds
K2CrO7Potassium dichromate, oxidizing agent; + sre um chromsäure zu bilden; 1°alk/ald->Carbonsre; 2°Alk->Ket; tox
H2SO4sulfuric acid, strong acid
PBr3Phosphorus tribromide, will convert carboxylic acids to acyl bromides and Alk. zu alkylbromid via SN2; Hell-Vollhard-Zelinsky Reaction
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HCNhydrogen cyanide, can use to make cyanohydrins
pyrrolidinesecondary amine, for Stork enamine reactions
NCSN-chlorosuccinimide, for chlorinations (similar to NBS)
FeBr3ferric bromide, used for Friedel-Crafts
AlCl3aluminum trichloride, used for Friedel Crafts
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Question Answer
Lilithium metal, used to make organolithium from alkyl bromide
Mgmagnesium metal, used to make Grignard from alkyl halide
DMSOpolar aprotic solvent - dimethyl sulfoxide
DMFpolar aprotic solvent - dimethyl formamide
LiAlH(OR)3less reactive derivative of LiAlH4, will reduce esters to aldehydes (only 1 equiv of hydride)
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CH2N2diazomethane, will take carboxylic acids to methyl esters
DIBAL-Hdiisobutylaluminum hydride, reducing agent, can take esters to aldehydes.
TsOHp-toluenesulfonic acid, p-TsOH - strong acid. OTs is also good leaving group
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