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| nucleophilic substitution on an alkyl halide |
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Definition
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name that reaction
[image] |
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Definition
| nucleophilic substitution on an alkyl halide |
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| acid-catalyzed hydration of alkenes |
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Definition
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Term
name that reaction
[image] |
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Definition
| acid-catalyzed hydration of alkenes |
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| oxymercuration-demurcuration |
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name that reaction
[image] |
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| oxymercuration-demurcuration |
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name that reaction
[image] |
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name that reaction
[image] |
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name that reaction
[image] |
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| addition of acetylides to carbonyl compounds |
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Definition
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name that reaction
[image] |
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Definition
| addition of acetylides to carbonyl compounds |
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name that reaction
[image] |
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Definition
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name that reaction
[image] |
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Definition
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Term
name that reaction
[image] |
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Definition
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Term
name that reaction
[image] |
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Definition
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Term
name that reaction
[image] |
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Definition
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Term
name that reaction
[image] |
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Definition
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Term
name that reaction
[image] |
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Definition
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mechanism for this rxn
[image] |
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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 |
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Definition
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Definition
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| oxidation using the DMP reagent |
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Definition
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Definition
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Definition
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Definition
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| converting an alcohol to an alkyl tosylate |
|
Definition
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Term
| substitution with an alkyl tosylate |
|
Definition
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Term
| elimination with an alkyl tosylate |
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Definition
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Definition
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Term
| how a tosylate ester (ROTs) is formed |
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Definition
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the process described here
[image] |
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Definition
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| how an alcohol is reduced |
|
Definition
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Term
|
Definition
| [image] and [image], respectively |
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| another way to reduce an alcohol |
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Definition
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Term
|
Definition
| [image] and [image], respectively |
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Definition
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Definition
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| mechanism for the rxn of a secondary or tertiary alcohol with ZnCl2 |
|
Definition
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|
Term
| mechanism for the rxn of a primary alcohol with ZnCl2 |
|
Definition
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Term
| some commercially available phosphorus halides that can be used to convert alcohols to alkyl halides |
|
Definition
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Term
| some useful reactions of phosphorus halides with alcohols |
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Definition
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Definition
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Definition
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Definition
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| mechanism for the reaction of an alcohol with PBr3 |
|
Definition
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Term
| mechanism for the rxn of an alcohol with thionyl chloride |
|
Definition
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Term
|
Definition
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Term
| the solvent used when using thionyl chloride ([image]) |
|
Definition
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|
Term
| the type of chloride used when converting primary alcohols to alkyl halides |
|
Definition
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|
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
|
|
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
|
|
Term
| the type of bromide used when converting tertiary alcohols to alkyl halides |
|
Definition
|
|
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
|
|
Term
| the mechanism by which the Lucas reagent (ZnCl2) reacts with secondary alcohols |
|
Definition
|
|
Term
| the mechanism by which the Lucas reagent (ZnCl2) reacts with tertiary alcohols |
|
Definition
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|
Term
| the mechanism by which HBr reacts with primary alcohols |
|
Definition
|
|
Term
| the mechanism by which HBr reacts with secondary alcohols |
|
Definition
|
|
Term
| the mechanism by which HBr reacts with tertiary alcohols |
|
Definition
|
|
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
|
|
Term
| rxn energy diagram for dehydration of an alcohol |
|
Definition
|
|
Term
| dehydration of a primary alcohol |
|
Definition
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Term
|
Definition
|
|
Term
|
Definition
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|
Term
| the mechanism that occurs when an alcohol is dehydrated to give an alkene |
|
Definition
elimination; this is unimolecular
[image] |
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Term
| the mechanism that occurs when bimolecular condensation of alcohol occurs |
|
Definition
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Term
|
Definition
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Term
|
Definition
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|
Term
| which has a more positive change in entropy (ΔS)? elimination or substitution? |
|
Definition
|
|
Term
| Gibbs free energy equation |
|
Definition
|
|
Term
|
Definition
| change in Gibbs free energy or "available energy"
Δ = TΔStotal |
|
|
Term
|
Definition
| change in enthalpy
ΔH = TΔSsurr |
|
|
Term
|
Definition
|
|
Term
|
Definition
| entropy change
ΔS = TΔSsystem |
|
|
Term
| the temperature at which dehydration of alcohols is favored over substitution |
|
Definition
|
|
Term
| the temperature at which substitution of alcohols is favored over dehydration |
|
Definition
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Term
|
Definition
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Term
|
Definition
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|
Term
| mechanism for pinacol rearrangement |
|
Definition
|
|
Term
| periodic acid cleavage of glycols |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
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Term
|
Definition
| [image] and [image], respectively |
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Term
|
Definition
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Term
|
Definition
| [image] and [image], respectively |
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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
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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] and [image], respectively
this is [image] |
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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]
this is [image]
[image] |
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Term
|
Definition
[image]
this is [image]
[image] |
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Term
|
Definition
[image]
this is [image]
[image] |
|
|
Term
|
Definition
[image]
this is [image]
[image] |
|
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Term
|
Definition
| [image] and [image], respectively |
|
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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|
Term
| cleavage of ether by loss of alkyl group |
|
Definition
|
|
Term
|
Definition
| cleavage of ether by loss of alkyl group |
|
|
Term
|
Definition
|
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Term
|
Definition
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Term
|
Definition
|
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Term
|
Definition
| [image] and [image], respectively |
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|
Definition
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|
Definition
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|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
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Term
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| synthesis of triisopropylsilyl (TIPS) |
|
Definition
|
|
Term
|
Definition
|
|
Term
| triisopropyl ether (TIPS) being used as a protecting group |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| example of triisopropyl ether being used as a protecting group |
|
Definition
|
|
Term
| synthesis of epoxide using epoxyacid |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| the mechanism that usually takes place in cleavage of ethers using HBr and HI |
|
Definition
|
|
Term
| mechanism of phenyl ethers reacting with HBr and HI |
|
Definition
|
|
Term
| mechanism of synthesizing thioethers using Williamson ether synthesis |
|
Definition
|
|
Term
| mechanism for epoxide synthesis using peroxyacid |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for base-promoted cyclization of halohydrins |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for forming a chlorohydrin |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| mechanism for displacing a chlorohydrin to form an epoxide |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for converting chlorohydrin into cyclic ether using 2,6-lutidine |
|
Definition
|
|
Term
| base-promoted cyclization of halohydrins |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
| [image], [image], and [image], respectively |
|
|
Term
| direct hydroxylation of alkenes |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for acid-catalyzed opening of epoxides in alcohol |
|
Definition
|
|
Term
|
Definition
| [image], [image], and [image], respectively |
|
|
Term
| opening epoxides using hydrohalic acids |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
|
Definition
|
|
Term
| rxn coordinate diagram comparing epoxides to acyclic ethers |
|
Definition
|
|
Term
| mechanism for base-catalyzed opening of epoxides |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| mechanism for opening epoxide using aqueous ammonia (NH3) |
|
Definition
|
|
Term
|
Definition
|
|
Term
| ethanolamine further reacting with epoxides |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| when peroxyacid converts alkene to epoxide |
|
Definition
|
|
Term
| when peroxyacid converts alkene to diol |
|
Definition
|
|
Term
| opening of epoxide under acid-catalyzed conditions |
|
Definition
|
|
Term
|
Definition
|
|
Term
| opening of epoxide under base-catalyzed conditions |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for base-catalyzed opening of an epoxide |
|
Definition
|
|
Term
| mechanism for acid-catalyzed opening of an epoxide |
|
Definition
|
|
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
|
|
Term
| opening of epoxide with Grignard or organolithium reagent |
|
Definition
|
|
Term
| mechanism for opening of epoxide with Grignard reagent |
|
Definition
|
|
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
|
|
Term
| Acid-catalyzed epoxide opening in water |
|
Definition
|
|
Term
|
Definition
|
|
Term
| Acid-catalyzed epoxide opening in alcohol |
|
Definition
|
|
Term
|
Definition
|
|
Term
| using hydrohalic acids to open epoxides |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
| base-catalyzed epoxide opening with alkoxodes or hydrides |
|
Definition
|
|
Term
|
Definition
|
|
Term
| base-catalyzed epoxide opening with organometallics |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
the product that does not result from this reaction
[image] |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
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Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| how benzo[a]pyrene, a polynuclear aromatic hydrocarbon, damages DNA |
|
Definition
|
|
Term
| mechanism of electrophilic aromatic substitution |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for the bromination of benzene |
|
Definition
|
|
Term
| energy diagram of the bromination of benzene |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| how the iodine cation (I+) is made |
|
Definition
| H+ + HNO3 + 1/2 I2 --> I+ + NO2 + H2O |
|
|
Term
|
Definition
|
|
Term
| mechanism for nitration of benzene |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
|
Definition
|
|
Term
| mechanism of the sulfonation of benzene |
|
Definition
|
|
Term
|
Definition
| [image] and [image], respectively |
|
|
Term
|
Definition
|
|
Term
| mechanism for protonation of the aromatic ring |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
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
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for ortho attack on an aromatic with an alkoxy group |
|
Definition
|
|
Term
| mechanism for meta attack on an aromatic with an alkoxy group |
|
Definition
|
|
Term
| mechanism for para attack on an aromatic with an alkoxy group |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for ortho attack on an alanine |
|
Definition
|
|
Term
| mechanism for para attack on an alanine |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for ortho attack on a nitrobenzene |
|
Definition
|
|
Term
| mechanism for meta attack on a nitrobenzene |
|
Definition
|
|
Term
| mechanism for para attack on a nitrobenzene |
|
Definition
|
|
Term
| rxn coordinate diagram of nitrobenzenes compared to benzene |
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing ortho attack |
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing meta attack |
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing para attack |
|
Definition
|
|
Term
|
Definition
|
|
Term
| rxn coordinate diagram of clhorobenzene vs. benzene |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| Friedel-Crafts alkylation |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism of a Friedel-Crafts alkylation |
|
Definition
|
|
Term
| another example of the mechanism of a Friedel-Crafts alkylation |
|
Definition
|
|
Term
|
Definition
|
|
Term
|
Definition
|
|
Term
| how BF3 converts an alcohol into a carbocation |
|
Definition
|
|
Term
| how electrophilic substitution on benzene occurs |
|
Definition
|
|
Term
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing ortho attack |
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing meta attack |
|
Definition
|
|
Term
| mechanism for a benzene with a halogen substituent doing para attack |
|
Definition
|
|
Term
|
Definition
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| rxn coordinate diagram of clhorobenzene vs. benzene |
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| Friedel-Crafts alkylation |
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| mechanism of a Friedel-Crafts alkylation |
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| another example of the mechanism of a Friedel-Crafts alkylation |
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| how BF3 converts an alcohol into a carbocation |
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| how electrophilic substitution on benzene occurs |
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| mechanism for Friedel-Crafts acylation |
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| [image] and [image], respectively |
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| [image] and [image], respectively |
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| [image] and [image], [image], and -OH, respectively |
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| [image] and H+, respectively |
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| mechanism for nucleophilic aromatic substitution (addition-elimination) |
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| the benzyne mechanism: elimination-addition |
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| mechanism for nucleophilic aromatic substitution (benzyne mechanism) |
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| how the organolithium reagent is made |
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| how the lithium organocuprate is made |
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| how coupling of the organocuprate with an alkyl, vinyl, or aryl halide is done |
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| Suzuki rxn (Suzuki coupling) |
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[image]
preserves stereochemistry |
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| how alkylboronate esters are made |
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| mechanism of the Suzuki rxn |
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| catalytic hydrogenation of aromatic rings |
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| mechanism for the Birch reduction |
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| [image] and H+, respectively |
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| mechanism for halogenation of a benzene's side chain |
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[image]
however, significant amounts of isomers are produced |
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| [image] and [image], respectively |
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| transition state for SN2 displacement of a benzylic halide |
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| mechanism for the tribromination of a phenol molecule |
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| [image], [image], and [image], respectively |
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| mechanism for electroophilic substitution of phenoxide anion to form salicylic acid |
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| [image] and [image], respectively |
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| [image] and [image], respectively |
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| [image] and [image], respectively |
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| how to protect the NH2 group on a benzene from the AlCl3 catalyst |
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| [image], [image], and [image], respectively |
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| [image] and [image], respectively |
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| [image] and [image], respectively |
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| sulfonation, forwards and backwards |
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| forward: [image]
reverse: H2O, heat |
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| [image], [image], and [image], respectively |
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| Friedel-Crafts alkylation |
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| nucleophilic aromatic substitution |
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| nucleophilic substitution at the benzylic position |
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| oxidation of phenols to quinones |
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| summary of electrophilic aromatic substitution of benzenes (DRAW THIS!!!!) |
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| summary of substitutions of aryl halides (DRAW THIS!!!!) |
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