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Organic Chemistry
Undergraduate 2
08/19/2019

Additional Organic Chemistry Flashcards

 


 

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Term
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Definition
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Definition
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Definition
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nucleophilic substitution on an alkyl halide
Definition
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Term
name that reaction
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Definition
nucleophilic substitution on an alkyl halide
Term
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Definition
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Term
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Definition
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Definition
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acid-catalyzed hydration of alkenes
Definition
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Term
name that reaction
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Definition
acid-catalyzed hydration of alkenes
Term
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Definition
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Term
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Definition
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Definition
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oxymercuration-demurcuration
Definition
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name that reaction
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Definition
oxymercuration-demurcuration
Term
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Definition
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Definition
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Definition
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hydroboration-oxidation
Definition
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Term
name that reaction
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Definition
hydroboration-oxidation
Term
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Definition
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Definition
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Definition
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syn dihydroxylation
Definition
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Term
name that reaction
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Definition
syn dihydroxylation
Term
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Definition
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Term
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Definition
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Definition
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anti dihydroxylation
Definition
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Term
name that reaction
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Definition
anti dihydroxylation
Term
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Definition
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Definition
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Definition
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addition of acetylides to carbonyl compounds
Definition
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Term
name that reaction
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Definition
addition of acetylides to carbonyl compounds
Term
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Definition
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name that reaction
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Definition
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Term
name that reaction
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Definition
tosylation
Term
name that reaction
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Definition
esterfication
Term
name that reaction
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Definition
reduction
Term
name that reaction
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Definition
substitution
Term
name that reaction
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Definition
oxidation
Term
name that reaction
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Definition
dehydration
Term
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Definition
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Term
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Definition
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Definition
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Definition
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Term
mechanism for this rxn
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Definition
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Term
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Definition
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Term
how a chromate ester is formed
Definition
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Term
how the chromate ester is eliminated and the carbinol atom is oxidized
Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
Swern oxidation
Definition
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Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
oxidation using the DMP reagent
Definition
[image]
Term
[image]
Definition
NaOCl (excess)-TEMPO
Term
[image]
Definition
-NaOCl-TEMPO
-Swern
-DMP
Term
[image]
Definition
-NaOCl-HOAc
-Swern
-DMP
Term
[image]
Definition
chromic acid
Term
[image]
Definition
PCC
Term
[image]
Definition
chromic acod or PCC
Term
converting an alcohol to an alkyl tosylate
Definition
[image]
Term
substitution with an alkyl tosylate
Definition
[image]
Term
elimination with an alkyl tosylate
Definition
[image]
Term
[image]
Definition
[image]
Term
how a tosylate ester (ROTs) is formed
Definition
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Term
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Definition
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Term
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Definition
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
reduction of an alcohol
Definition
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Term
the process described here
[image]
Definition
reduction of an alcohol
Term
how an alcohol is reduced
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
another way to reduce an alcohol
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
NaBr, H2SO4
Term
[image]
Definition
ZnCl2
Term
mechanism for the rxn of a secondary or tertiary alcohol with ZnCl2
Definition
SN1 (fast) [image]
Term
mechanism for the rxn of a primary alcohol with ZnCl2
Definition
SN2 (slow) [image]
Term
some commercially available phosphorus halides that can be used to convert alcohols to alkyl halides
Definition
-PBr3 -PCl3 -PCl5
Term
some useful reactions of phosphorus halides with alcohols
Definition
[image]
Term
[image]
Definition
PBr3
Term
[image]
Definition
P/I2
Term
[image]
Definition
PBr3
Term
mechanism for the reaction of an alcohol with PBr3
Definition
[image]
Term
mechanism for the rxn of an alcohol with thionyl chloride
Definition
[image]
Term
[image]
Definition
[image]
Term
the solvent used when using thionyl chloride ([image])
Definition
dioxane ([image])
Term
the type of chloride used when converting primary alcohols to alkyl halides
Definition
SOCl2
Term
the type of bromide used when converting primary alcohols to alkyl halides
Definition
PBr3 or HBr (HBr works only in selected cases)
Term
the type of iodide used when converting primary alcohols to alkyl halides
Definition
P/I2 that is, 2P + 3I2 <--> 2PI3
Term
the type of chloride used when converting secondary alcohols to alkyl halides
Definition
SOCl2 (SN1 mechanism) PCl3 or PCl5 (SN2 mechanism)
Term
the type of bromide used when converting secondary alcohols to alkyl halides
Definition
PBr3
Term
the type of iodide used when converting secondary alcohols to alkyl halides
Definition
P/I2 that is, 2P + 3I2 <--> 2PI3 this works only in selected cases
Term
the type of chloride used when converting tertiary alcohols to alkyl halides
Definition
HCl
Term
the type of bromide used when converting tertiary alcohols to alkyl halides
Definition
HBr
Term
the type of iodide used when converting tertiary alcohols to alkyl halides
Definition
HI

this works only in selected cases
Term
the mechanism by which the Lucas reagent (ZnCl2) reacts with primary alcohols
Definition
SN2
Term
the mechanism by which the Lucas reagent (ZnCl2) reacts with secondary alcohols
Definition
SN1
Term
the mechanism by which the Lucas reagent (ZnCl2) reacts with tertiary alcohols
Definition
SN1
Term
the mechanism by which HBr reacts with primary alcohols
Definition
SN2
Term
the mechanism by which HBr reacts with secondary alcohols
Definition
SN1
Term
the mechanism by which HBr reacts with tertiary alcohols
Definition
SN1
Term
the mechanism by which phosphorus trihalides react with primary alcohols
Definition
form a leaving group, then SN2
Term
the mechanism by which phosphorus trihalides react with secondary alcohols
Definition
form a leaving group, then SN2
Term
the mechanism by which phosphorus trihalides react with tertiary alcohols
Definition
they react very poorly with tertiary alcohols, but form a leaving group, then SN2
Term
mechanism by which thionyl chloride (SOCl2) reacts with alcohol
Definition
resembles Sn1, but retains stereochemistry because the halide is delivered by the leaving group
Term
why reactions with thionyl chloride (SOCl2) retain stereochemistry
Definition
because the halide is delivered by the leaving group
Term
the mechanism by which alcohol dehydration takes place
Definition
usually the E1 mechanism
Term
rxn energy diagram for dehydration of an alcohol
Definition
[image]
Term
dehydration of a primary alcohol
Definition
[image]
Term
E1 mechanism
Definition
[image]
Term
E2 mechanism
Definition
[image]
Term
the mechanism that occurs when an alcohol is dehydrated to give an alkene
Definition
elimination; this is unimolecular
[image]
Term
the mechanism that occurs when bimolecular condensation of alcohol occurs
Definition
substitution
[image]
Term
[image]
Definition
H2SO4, 180°C
Term
[image]
Definition
H2SO4, 140°C
Term
which has a more positive change in entropy (ΔS)? elimination or substitution?
Definition
elimination
Term
Gibbs free energy equation
Definition
ΔG = ΔH - TΔS
Term
ΔG
Definition
change in Gibbs free energy or "available energy" Δ = TΔStotal
Term
ΔH
Definition
change in enthalpy ΔH = TΔSsurr
Term
T
Definition
temperature (Kelvins)
Term
ΔS
Definition
entropy change ΔS = TΔSsystem
Term
the temperature at which dehydration of alcohols is favored over substitution
Definition
around 140°C
Term
the temperature at which substitution of alcohols is favored over dehydration
Definition
around 180°C
Term
pinacol rearrangement
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for pinacol rearrangement
Definition
[image]
Term
periodic acid cleavage of glycols
Definition
[image]
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
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Term
[image]
Definition
[image] and [image], respectively
Term
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
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Definition
[image]
Term
[image]
Definition
[image] and [image], respectively

this is [image]
Term
[image]
Definition
[image]

this is [image]
Term
[image]
Definition
[image]

this is [image]
Term
[image]
Definition
[image]

this is [image]
Term
[image]
Definition
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this is [image]
Term
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Definition
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this is [image]
Term
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Definition
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Term
[image]
Definition
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this is [image]

[image]
Term
[image]
Definition
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this is [image]

[image]
Term
[image]
Definition
[image]

this is [image]

[image]
Term
[image]
Definition
[image]

this is [image]

[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
α Cleavage of an ether
Definition
[image]
Term
[image]
Definition
α Cleavage of an ether
Term
cleavage of ether by loss of alkyl group
Definition
[image]
Term
[image]
Definition
cleavage of ether by loss of alkyl group
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
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Definition
[image]
Term
[image]
Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Definition
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Term
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Definition
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Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
synthesis of triisopropylsilyl (TIPS)
Definition
[image]
Term
[image]
Definition
[image]
Term
triisopropyl ether (TIPS) being used as a protecting group
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
example of triisopropyl ether being used as a protecting group
Definition
[image]
Term
synthesis of epoxide using epoxyacid
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
the mechanism that usually takes place in cleavage of ethers using HBr and HI
Definition
SN2
Term
mechanism of phenyl ethers reacting with HBr and HI
Definition
[image]
Term
mechanism of synthesizing thioethers using Williamson ether synthesis
Definition
[image]
Term
mechanism for epoxide synthesis using peroxyacid
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for base-promoted cyclization of halohydrins
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for forming a chlorohydrin
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
mechanism for displacing a chlorohydrin to form an epoxide
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for converting chlorohydrin into cyclic ether using 2,6-lutidine
Definition
[image]
Term
base-promoted cyclization of halohydrins
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image], [image], and [image], respectively
Term
direct hydroxylation of alkenes
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for acid-catalyzed opening of epoxides in alcohol
Definition
[image]
Term
[image]
Definition
[image], [image], and [image], respectively
Term
opening epoxides using hydrohalic acids
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
rxn coordinate diagram comparing epoxides to acyclic ethers
Definition
[image]
Term
mechanism for base-catalyzed opening of epoxides
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
mechanism for opening epoxide using aqueous ammonia (NH3)
Definition
[image]
Term
[image]
Definition
[image]
Term
ethanolamine further reacting with epoxides
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
when peroxyacid converts alkene to epoxide
Definition
in the absence of H3O+
Term
when peroxyacid converts alkene to diol
Definition
in the presence of H3O+
Term
opening of epoxide under acid-catalyzed conditions
Definition
[image]
Term
[image]
Definition
[image]
Term
opening of epoxide under base-catalyzed conditions
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for base-catalyzed opening of an epoxide
Definition
SN2 [image]
Term
mechanism for acid-catalyzed opening of an epoxide
Definition
[image]
Term
the carbon that gets attacked in acid-catalyzed opening of epoxides
Definition
the more substituted one, since it has more + charge
Term
the carbon that gets attacked in base-catalyzed opening of epoxides
Definition
the less substituted one, since it's less hindered
Term
comparison of acid-catalyzed and base-catalyzed opening of epoxide
Definition
[image]
Term
opening of epoxide with Grignard or organolithium reagent
Definition
[image]
[image]
Term
mechanism for opening of epoxide with Grignard reagent
Definition
[image]
[image]
Term
how epoxy resins form good quality glues as they harden
Definition
by polymerizing with each other
[image]
[image]
[image]
Term
how cross-links are formed between chains of epoxy polymers in glue
Definition
[image]
Term
Acid-catalyzed epoxide opening in water
Definition
[image]
Term
[image]
Definition
[image]
Term
Acid-catalyzed epoxide opening in alcohol
Definition
[image]
Term
[image]
Definition
[image]
Term
using hydrohalic acids to open epoxides
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
base-catalyzed epoxide opening with alkoxodes or hydrides
Definition
[image]
Term
[image]
Definition
[image]
Term
base-catalyzed epoxide opening with organometallics
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
the product that does not result from this reaction
[image]
Definition
[image]
Term
[image]
Definition
[image]
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
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[image]
Definition
[image]
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[image]
Definition
[image]
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[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
how benzo[a]pyrene, a polynuclear aromatic hydrocarbon, damages DNA
Definition
[image]
Term
mechanism of electrophilic aromatic substitution
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for the bromination of benzene
Definition
[image]
Term
energy diagram of the bromination of benzene
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
how the iodine cation (I+) is made
Definition
H+ + HNO3 + 1/2 I2 --> I+ + NO2 + H2O
Term
[image]
Definition
[image]
Term
mechanism for nitration of benzene
Definition
[image]
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
mechanism of the sulfonation of benzene
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
mechanism for protonation of the aromatic ring
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
the rate-limiting step for electrophilic aromatic substitution
Definition
the 1st step (formation of the sigma complex)
Term
rxn coordinate diagram for aromatics substituted at different locations
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for ortho attack on an aromatic with an alkoxy group
Definition
[image]
Term
mechanism for meta attack on an aromatic with an alkoxy group
Definition
[image]
Term
mechanism for para attack on an aromatic with an alkoxy group
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for ortho attack on an alanine
Definition
[image]
Term
mechanism for para attack on an alanine
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for ortho attack on a nitrobenzene
Definition
[image]
Term
mechanism for meta attack on a nitrobenzene
Definition
[image]
Term
mechanism for para attack on a nitrobenzene
Definition
[image]
Term
rxn coordinate diagram of nitrobenzenes compared to benzene
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing ortho attack
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing meta attack
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing para attack
Definition
[image]
Term
[image]
Definition
[image]
Term
rxn coordinate diagram of clhorobenzene vs. benzene
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
Friedel-Crafts alkylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
AlCl3
Term
mechanism of a Friedel-Crafts alkylation
Definition
[image]
Term
another example of the mechanism of a Friedel-Crafts alkylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
how BF3 converts an alcohol into a carbocation
Definition
[image]
Term
how electrophilic substitution on benzene occurs
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing ortho attack
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing meta attack
Definition
[image]
Term
mechanism for a benzene with a halogen substituent doing para attack
Definition
[image]
Term
[image]
Definition
[image]
Term
rxn coordinate diagram of clhorobenzene vs. benzene
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
Friedel-Crafts alkylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
AlCl3
Term
mechanism of a Friedel-Crafts alkylation
Definition
[image]
Term
another example of the mechanism of a Friedel-Crafts alkylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
how BF3 converts an alcohol into a carbocation
Definition
[image]
Term
how electrophilic substitution on benzene occurs
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
Friedel-Crafts acylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for Friedel-Crafts acylation
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
Clemmensen reduction
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
[image]
Definition
[image] and [image], [image], and -OH, respectively
Term
Gatterman-Koch synthesis
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
(heat, pressure)
Term
[image]
Definition
[image] and H+, respectively
Term
mechanism for nucleophilic aromatic substitution (addition-elimination)
Definition
[image]
Term
[image]
Definition
[image]
Term
the Dow process
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
the benzyne mechanism: elimination-addition
Definition
[image]
[image]
Term
mechanism for nucleophilic aromatic substitution (benzyne mechanism)
Definition
[image]
[image]
Term
how the organolithium reagent is made
Definition
[image]
Term
how the lithium organocuprate is made
Definition
[image]
Term
how coupling of the organocuprate with an alkyl, vinyl, or aryl halide is done
Definition
[image]
Term
the Heck rxn
Definition
[image]
Term
[image]
Definition
[image]
Term
Suzuki rxn (Suzuki coupling)
Definition
[image]
Term
[image]
Definition
[image]
preserves stereochemistry
Term
how alkylboronate esters are made
Definition
[image]
Term
[image]
Definition
2 Li and [image]
Term
mechanism of the Suzuki rxn
Definition
[image]
Term
clhorination of benzene
Definition
[image]
Term
[image]
Definition
[image]
Term
catalytic hydrogenation of aromatic rings
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
Birch reduction
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for the Birch reduction
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and H+, respectively
Term
[image]
Definition
[image]
Term
mechanism for halogenation of a benzene's side chain
Definition
[image]

however, significant amounts of isomers are produced
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image]
Term
transition state for SN2 displacement of a benzylic halide
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and [image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image]
Term
mechanism for the tribromination of a phenol molecule
Definition
[image]
Term
[image]
Definition
[image], [image], and [image], respectively
Term
mechanism for electroophilic substitution of phenoxide anion to form salicylic acid
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
how to protect the NH2 group on a benzene from the AlCl3 catalyst
Definition
[image]
Term
[image]
Definition
[image]
Term
[image]
Definition
[image], [image], and [image], respectively
Term
[image]
Definition
[image] and [image], respectively
Term
[image]
Definition
[image]
Term
[image]
Definition
[image] and [image], respectively
Term
sulfonation, forwards and backwards
Definition
[image]
Term
[image]
Definition
forward: [image] reverse: H2O, heat
Term
[image]
Definition
[image], [image], and [image], respectively
Term
halogenation
Definition
[image]
Term
nitration
Definition
[image]
Term
sulfonation
Definition
[image]
Term
Friedel-Crafts alkylation
Definition
[image]
Term
Friedel-Crafts acylation
Definition
[image]
Term
Gatterman-Koch synthesis
Definition
[image]
Term
nucleophilic aromatic substitution
Definition
[image]
Term
organocuprate coupling
Definition
[image]
Term
Heck coupling
Definition
[image]
Term
Suzuki coupling
Definition
[image]
Term
chlorination
Definition
[image]
Term
catalytic hydrogenation
Definition
[image]
Term
Birch reduction
Definition
[image]
Term
Clemmensen reduction
Definition
[image]
Term
permangenate oxidation
Definition
[image]
Term
side-chain halogenation
Definition
[image]
Term
nucleophilic substitution at the benzylic position
Definition
[image]
Term
oxidation of phenols to quinones
Definition
[image]
Term
summary of electrophilic aromatic substitution of benzenes (DRAW THIS!!!!)
Definition
[image]
Term
summary of substitutions of aryl halides (DRAW THIS!!!!)
Definition
[image]
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