Chem Flashcards
ε0 is
vacuum permitivity
µ0 is
vacuum permeability
Fukuyama coupling turns.. via… to..
thioester and organozinc halide palladium catalyst ketone
Krebs cycle pyruvate to Alpha ketoglutarate
PYRUVATE + CoA Sulfhydryl CO2 + ACETYL-COA + Oxaloacetate + Water CITRATE - water ACONITATE + water D-ISOCITRATE + NAD+ ALPHA-KETOGLUTARATE + NADH
Prato reaction (Prato 1,3 dipolar cycloaddtion) does
fullerene + amino acid sarcosine + ylide
in toluene
= fullerene derivative
2,3-Wittig rearrangement does this
allylic ether turns to a homoallylic alcohol
Claisen condensation does
ester + ester(or carbonyl compound) + strong base
=beta-keto ester
Adams’s catalyst formula, and used in?
Platinum 4 oxide (PtO2)
hydrogenation
Acyloin condensation does this
two esters and sodium
reduced to
(alpha-hydroxy)ketone or acyloin
Oxidation of primary alcohols
Primary alcohols + oxygen
= aldehyde + H2O + O
=carboxylic acid
Oxidation of secondary alcohols
secondary alcohol + oxygen
= ketone
found Aldol reaction
Borodin and Wurtz
Michael addition/reaction does
addition of a carbanion to an alpha, beta-unsaturated carbonyl compound
Makes carbon carbon bonds
Mukaiyama reaction is more complex form of
Michael Addition
Mukaiyama reaction does
silyl enol ethers +aldehydes
w/ Lewis acid catalyst
= aldol
Amadori rearrangement does this
adds ammonia to sugar to a sugar with an amine
Maillard reaction reacts
Amino acids and reducing sugar
the Andrussow process does this
methane + ammonia + oxygen
w/ platinum catalyst
= hydrogen cyanide
Appel reaction does this
(R-group) bond to hydroxyl + CCl4 + triphenylphosphine
= (R-group) bonded to Chlorine
1,3-Dipolar cycloaddition does this (specifically) Huisgen cycloaddition) does this
organic azide + alkyne
= 1,2,3-triazole
Michaelis-Arbuzov reaction does
(Trialkyl phosphite + alkyl halid = phosphonate)
(Aromatic) nitration does
an aromatic compound(benzene) has a nitro group added to it
Presense of sulfuric acid as catalyst
is electrophilic aromatic substitution
functional group is NO2
Nitro group
Arndt–Eistert reaction does this
turns carboxylic acid into a bigger one through a Wolff Rearrangement
uses Diazomethane to do this (CH2N2) and Silver II Oxide
are compounds with two R groups and a nitrogen double bond
Azo compound
Azo coupling does
reaction between a diazonium compound and another aromatic compound that produces an azo compound
Azo compounds are used to make
Dyes
Baeyer-Villiger oxidation does
ketone + hydogen peroxide(or peroxy acid)
+ mCPBA reagent
= ester
Bakelite is
Phenol and formaldehyde
Scholl reaction does this
coupling reaction between two arenes
with Lewis acid and protic acid
Arene is a
**aromatic hydrocarbon **hydrocarbon with alternating double and single bonds between carbon atoms forming rings
Balz-Schiemann reaction does and is?
similar to the Sandmeyer reaction
adds Flourine to benzene to make fluorobenzene
Bamberger rearrangement does
Rearranges
Bamford–Stevens reaction does
decomposes diazoalkanes in aprotic solutions
has carbene intermediate
makes alkenes
Bartoli reaction does
nitroarenes w/ vinyl Grignard reagent
to indoles
Bechamp reduction
Converts aromatic Nitro compounds to aniline form
Beckmann rearrangement does
acid catalyzed rearragnement
oxime to amide
Claisen rearrangement does
allyl vinyl ether + heat = unsaturated carbonyl
Feist–Benary synthesis makes
Furan
Benedict’s solution tests for (colors?)
made of?
Tests for reducing sugars
has copper 2+ ions
green: .5%
yellow: 1%
Orange: 1.5%
Red: 2.0%
What is an alkyation
Adding an alkyl group to a molecule
What’s an acyl group
derived by the removal of one or more hydroxyl groups from an oxoacid
is essentially a carbonyl group bonded to an r group and something else(nitrogen, hydrogen, r group, etc)
Bergman reaction does this
a rearrangment reaction that turns enediyne(dialkyne) to a cyclic compound(benzene)
Seyferth Gilbert homologation does this
turns aryl ketone (or aldehyde)
w/ dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide
into alkynes
Ohira-Bestmann reagent is used in the?
Seyferth-Gilbert homologation (makes alkynes)
is dimethyl-1-diazo-2-oxopropylphosphonate
Bingel reaction does
cyclopropanation reaction to a fullurene
in presence of a base
Birch reduction does
organic reduction of organic ring
in liquid ammonia
with alkali metal (Sodium, lithium, potassium)
in an alcohol (ethanol or tert butanol)
what is an indole
six-membered** benzene ring fused to a five-membered nitrogen**-containing pyrrole ring
what is a pyrrole
conjugated five-membered ring in which one carbon is replaced by a nitrogen
Bodroux reaction does
Turns carboxylic acid + Grignard reagent w/ aniline to Amide
Boord olefin synthesis does
Ethers with a halogen make an alkene
there is a Grignard reagent intermediate
catalyzed by zinc or magnesium
Hunsdiecker-Borodin reaction does this
BORODIN THE COMPOSER
silver salts of carboxylic acids + halogens make organic halides
Bosch–Meiser process does
2NH3 + CO2 [is in equilibrium with] H2N-COONH4
(2)Ammonia and CO2 makes urea
Bouveault–Blanc reaction does
Reduction
Ester is reduced to primary alcohol
using ethanol and sodium metal
Schmidt reaction does
- turns carboxylic acid to amines
- turns ketones to amides
uses hydrozoic acid (rxn needs azide group)
imine is this kind of group
a carbon–nitrogen double bond
differentiate ketimine and aldimine
aldimine
ketimine
Bredt’s rule says
double bond can’t be at head of bridged ring system
Hydroboration–oxidation reaction does this
turns alkenes into alcohols
by addition of Boron hydride, Hydrogen peroxide, and hydoxyl
done in tetrahydrofuran
Buchwald–Hartwig reaction does this
palladium-catalyzed cross-coupling of amines with aryl halides
creating carbon nitrogen double bonds
Cadiot- Chodkiewicz coupling does this
coupling reaction between a terminal alkyne and a haloalkyne
catalyzed by copper 1 salt and amine base
makes alkyne(diacetylene)
Cannizzaro Reaction does this
reacts: two aldehydes
Produces: (through oxidation)carboxylic acid and (through reduction)an alcohol
Reducing a carbonyl typically makes
alcohols
CBS reaction stands for and does
Corey Baksi Shibati reduction
ketone is reduced to make alcohol
it’s n/s catalyst is a boron compound
CBS catalyst is
and has
Boron
Ph is phenol
Chugaev reaction is this
an elimination reaction
alcohols have water eliminated to make alkenes
Claisen condensation does this
reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base,
Makes β-keto ester or a β-diketone
Collins reagent is
complex of chromium(VI) oxide with pyridine in dichloromethane
alternative when oxidizing secondary alcohols to ketones
DOES SAME AS JONES REAGENT(REACTION)
Cope reaction does and is?
a elimination
elimnation of amine to make alkene and hydroxylamine
Cope rearrangment does
sigmatropic rearrangement of dienes
(sigma bond moves)
Corey–Fuchs reaction does
transform an aldehyde into an alkyne
Corey–Kim reaction is a
oxidation
makes aldehydes and ketones from primary and secondary alcohols
Corey & Winter name a reaction that does
turns diols to alkenes
diol is a
di alchohol
Coupling reaction is a?
reactions where two hydrocarbon fragments are coupled with the aid of a metal catalyst
Criegee mechanism does this
alkene and ozone react in 1,3 dipolar cycloaddition
makes alcohols, aldehydes, ketones, carbox.. etc
Curtius rearrangement(degradation etc) does this
rearrangement of an acyl azide to an isocyanate
removal of N2 gas
Dakin reaction does this
redox reaction
reduces phenyl aldehyde(or ketone) to make a benzenediol
Dess–Martin reagent is used for
and is?
oxidize primary alcohols to aldehydes and secondary alcohols to ketones
has IODINE
Diisobutylaluminium hydride (DIBAL-H)
is used for
made of?
- co catalyst for polymerization of alkenes
- Reducing agent turning esters and nitriles to aldehydes
2 Aluminum
Dieckmann condensation
is
intramolecular form of Claisen condensation,
reaction of diesters with base to give β-ketoesters
Diels–Alder reaction is?
cycloaddition between a conjugated diene and a substituted alkene to make a cyclohexene
Dutt-Wormall reaction does
diazonium salt reacts with a sulfonamide to make azides
Eder reaction makes this
** Hg**2Cl2(s) + 2[NH4+][Cl−] + 2CO2
IT MAKES CO2
Edman degradation does
sequencing amino acids in a peptide (breaking peptide bonds)
Einhorn–Brunner reaction does
reaction of imides w/ hydrazines to make triazoles
what is an elimination reaction
and 2 types
Reaction where 2 subsituents are removed from molecule
E1: two step mechanism
E2: one step mechanism
Emde degradation is..?
related to Hoffman eliminiation
it reduces ammonium cation to tertiary amine
uses sodium amalgam
Eschweiler–Clarke reaction does this
primary (or secondary)amine is methylated using excess **formic acid **and formaldehyde
Favorskii rearrangment does this
turns a alkoxide base into a ester
or amine to an amide
in basic conditions
Fehling solution tests for
and is made of
tests for aldehyde or ketone, aldehydes turn it positive
Copper 2 sulfate and potassium sodium tartrate(rochelle salt)
is deep blue originally, turns red precipitate in aldehyde
tests for monosaccharides in urine
Fenton’s reagent is
and does?
hydrogen peroxide and iron catalyst
used to oxidize
Fischer indole synthesis
produces the indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions
Fischer oxazole synthesis
does
synth. oxazole from cyanohydrins and aldehydes in the presence of anhydrous hydrochloric acid
Fischer glycosidation
is?
reaction of an aldose or ketose with an alcohol in the presence of an acid catalyst to make glycoside
Fischer estrification does..?
** carboxylic acid** and an alcohol in the presence of an** acid catalyst** makes ester
Fischer–Tropsch process does
converts a mixture of carbon monoxide and hydrogen into liquid hydrocarbons
Fowler’s solution is
a solution containing 1% potassium arsenite (KAsO2)
Frankland was the first person to make
organozinc compounds
Free-radical halogenation is?
A halogenation of usually **alkanes **under UV light
makes chloroform
Friedel Crafts acylation is?
It is the addition of an acyl group to a benzene ring
using acyl chloride and and an Lewis acid catalyst(like aluminum chloride and cuprous chloride)
Friedel Crafts alkylation is..?
alkylation of an aromatic ring with an** alkyl halide** using a strong Lewis acid catalyst
(ferric chloride is catalyst)
Fries rearrangement does
rearrangement reaction of a phenolic ester to a hydroxy aryl ketone by catalysis of** Lewis acid**
Fujimoto-Belleau reaction does
forms cyclic α-substituted α,β-unsaturated **ketones **from enol lactones
** is a Grignard reaction/reagent **
Fukuyama coupling does this
a coupling reaction taking place between a thioester and an** organozinc halide**
w/ Palladium catalyst
makes ketone
Gabriel synthesis does
transforms primary** alkyl halides** into primary amines.
reaction uses potassium phthalimide
Gassman synthesis does
turns aniline into indoles
uses **Raney nickel **to desulfurization in it
Gattermann Koch reaction
does
a Friedel–Crafts acylation reaction in which** carbon monoxide and hydrochloric acid and AlCl3 catalyst** make benzaldehyde
Gilman reagent is and does?
used to replace halides with r groups
Glaser Coupling does this
combines two aldehydes(ethyne) via copper chloride or bromide
Gomberg names one..
it is made of?
a radical(the first)
Triphenylmethyl radical
Grignard reaction does this
reaction in which alkyl, vinyl, or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in an aldehyde or ketone
Grubbs’ catalyst is for
and is made of
used for olefin metathesis
main is ruthenium
Haber–Weiss reaction does
.O2- + H2O2 → •OH + OH- + O2
Superoxide and Hydrogen peroxide make hydroxyl radical
Hammett equation says
where K is equillibrium constant
sigma is substituent constant
p is reaction constant
ALSO
k is reaction rate
Hammett function tests for
acidity
conj acid: BH+
Base: B
Hammond’s postulate is for
concerns the transition state of organic chemical reactions
Hantzsch type
ester
Haworth projection is..?
A projection of a cyclic monosaccharide
Thicker line means atoms closer to viewer
Fischer projection is?
Used to show carbohydrates
Haworth phenanthrene synthesis is?
A type of Friedel Crafts reaction
uses two reductions Wolf Kishner or Clemmonson
Mizoroki-Heck reaction does this
reaction of an unsaturated halide with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene
Herz reaction does
conversion of an aniline-derivative to a Herz-salt disulfur dichloride,
followed by hydrolysis of this Herz-salt (2) to the corresponding sodium thiolate
makes THIOLS
Ellman’s reagent is and tests for?
DTNB
quantify the number or concentration of thiol groups in a sample
Herzig–Meyer alkimide group determination is for
basically its a reverse Hoffman elimination
Hinsberg reaction is?
is a chemical test for the detection of amines
reagent contains an aqueous sodium(potassium) hydroxide solution and** benzenesulfonyl chloride**
Hofmann elimination is?
also known as exhaustive methylation
an amine is reacted to create a tertiary amine and an alkene by treatment with excess** methyl iodide**
followed by treatment with silver oxide, water, and heat
What is an amide
Is where nitrogen is bonded to a carbonyl bonded to an r group
(first especially)
Hofmann rearrangment (degredation) does
organic reaction of a primary amide to a primary amine with one fewer carbon atoms
has isocyanate intermediate
Imide is a?
Nitrogen thats bonded to two acyl groups and one r group
Isocyanate is a?
functional group with the formula R–N=C=O
Horner–Wadsworth–Emmons reaction is
reaction of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes
is a Wittig reaction
Houben–Hoesch reaction does this
reaction in which a nitrile reacts with an arene compound to form an aryl ketone
Hunsdiecker reaction does this
organic reaction of silver salts of carboxylic acids with halogens to give organic halides
Ing-Manske reaction is?
basically is Gabriel Synthesis
alkyl halides to amines
Jacobsen reaction is a type of ?
Epoxidation
also a Sharpless epoxidation
Jacobsen rearrangement does this
migration of an alkyl group derived from a polyalkyl- or polyhalobenzene
in a sulfonic acid(sometimes sulfuric acid)
Jones oxidation
is?
organic reaction for the oxidation of primary alcohols to carboxylic acids and secondary alcohols to ketones
reagent is solution of chromium trioxide in dilute sulfuric acid and acetone
Ullmann condensation(synth) does this
a phenol is coupled to an aryl halide to create a diaryl ether in the presence of a copper compound
Julia reaction does this
reaction of phenyl sulfones (1) with aldehydes (or ketones) to give alkenes
a type of WIttig reaction
Willgerodt rearrangement does this
reaction converting an aryl alkyl ketone to the corresponding amide by reaction with ammonium polysulfide
Knoevenagel condensation(reaction) does this
sorta an aldol condensation
nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated
Paal–Knorr synthesis does this
reaction that generates either** furans, pyrroles, or thiophenes** from 1,4-diketones
- furan synthesis requires an acid catalyst
- pyrrole synthesis a primary amine participates
- for thiophene compound phosphorus pentasulfide:
Kochi reaction is
variation on the Hunsdiecker reaction
reaction for the decarboxylation of carboxylic acids to alkyl halides with lead tetraacetate and a lithium chloride or other lithium salts
Kolbe–Schmitt reaction does
a carboxylation reaction that proceeds by heating sodium phenolate (the sodium salt of phenol) with **carbon dioxide **treated w/ sulfuric acid
makes salicylic acid
a carboxylic acid
Kolbe synthesis does this
alkylhalide with a metal cyanide makes alkyl nitriles
Leimgruber-Batcho reaction does this
produce indoles from o-nitrotoluenes
effected by Raney nickel and hydrazine is used
Lindlar catalyst is?
And does?
a** heterogeneous catalyst** that consists of** palladium** deposited on calcium carbonate or barium sulfate and treated with various forms of lead
used for the hydrogenation of alkynes to alkenes
Lossen rearrangement does this
conversion of a hydroxamic acid(made from ester) (1) to an isocyanate
Lucas’ reagent is?
tests for?
solution of anhydrous zinc chloride in concentrated** hydrochloric acid**
used to classify alcohols of low molecular weight
Luche reaction is?
a reduction
converts ketones to alcohols
with lanthanoid chlorides such as** cerium(III) chloride and sodium borohydride**
Madelung synthesis does this
produces indoles by the intramolecular** cyclization of N-phenylamides** using strong base at high temps
Mannich reaction does
consists of an amino alkylation
formaldyhyde, an amine(or ammonia), and a carbonyl reaction
makes beta-amino carbonyl, a Mannich base
Markovnikov’s rule says?
when adding acid HX to unsym. alkene, hydrogen attaches to carbon with most hydrogens
halogen adds to group with most alkyl sustituents
left product is good
McFadyen-Stevens reaction does
base-catalyzed thermal decomposition of acylsulfonylhydrazides to aldehydes
McMurry reaction(coupling) does this
reaction in which two ketone or aldehyde groups are coupled to an alkene using** titanium chloride** compound such as titanium(III) chloride and a reducing agent
alkene is made
Meerwein–Ponndorf–Verley reaction is a?
Reduction
the** reduction of ketones and aldehydes** to their corresponding alcohols utilizing aluminium alkoxide catalysis in the presence of a sacrificial alcohol
Oppenauer reaction is this
an oxidation
selectively oxidizing secondary alcohols to ketones The alcohol is oxidized with** aluminium isopropoxide** in excess acetone
opposite of ** Meerwein-Ponndorf-Verley reduction**
Meisenheimer complex is this
1:1 reaction adduct between an** arene carrying electron withdrawing groups** and nucleophile
Mitsunobu reaction
converts **alcohol **to various funct. group via inversion of stereochemistry
makes ester via triphenylphosphine and **DEAD **or DIAD
Nef reaction does this
reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (1) to an aldehyde or a ketone (3) and nitrous oxide
with sulfuric acid
Negishi coupling does this
reaction in organic chemistry involving an organozinc compound, an organic halide and a nickel or palladium catalyst creating a new carbon–carbon covalent bond
Nicholas reaction does this
reaction where a dicobalt octacarbonyl-stabilized propargylic cation is reacted with a nucleophile.
Oxidative demetallation gives the desired alkylated alkyne
Ninhydrin is?
molecule, that binds with ammonia or amines to make Ruhemann’s purple
Noyori asymmetric reaction is this
hydrogenation
reaction for the enantioselective hydrogenation of ketone, aldehydes, and imines. This reaction exploits using chiral ruthenium catalysts
makes hydroxyl group
Nozaki–Hiyama–Kishi reaction
does this
is a nickel/chromium coupling reaction forming an alcohol from the reaction of an aldehyde with an allyl or vinyl halide
Passerini reaction is this
reaction involving an isocyanide, an aldehyde (or ketone), and a carboxylic acid to form a α-acyloxy amide
Pauson–Khand reaction does this
cycloaddition between an alkyne, an alkene and** carbon monoxide** to form a α,β-cyclopentenone
Payne rearrangement does this
isomerization, under basic conditions, of 2,3-epoxy alcohols to isomeric 2,3-epoxy alcohols with inversion of configuration
Pechmann condensation does
is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a β-carbonyl group
under **acidic **condition
Petasis reaction is this
reaction of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines
Petasis reagent is?
organotitanium compound with the formula Cp2Ti(CH3)2
Zincke reaction
a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine
Zincke names a type of..?
aldehyde
Peterson reaction does
reaction of α-silyl carbanions 1 with ketones (or aldehydes) to form a β-hydroxysilane 2 which eliminates to form alkenes
Pinacol rearrangement does
converting a 1,2-diol to a carbonyl compound
what is a pinacol
a diol with vicinal hydroxyls(right next to each other)
