Term
| Organolithium Reagents (R-Li) |
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Definition
Properties: Extremely strong bases, good nucleophiles
Uses: Will react with groups containing acidic hydrogens, aldehydes, ketones, esters, carboxylic acids, and epoxides.
Formation: When reacting with carboxylic compounds (compounds containing an oxygen, will add a hydrogen to form an alcohol and add its R group to the central carbon) |
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Term
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Definition
Properties: Very strong base, but poor nucleophile
Uses: Deprotonation of alkynes to make them excellent nucleophiles. (Used as an example in synthesis problem) |
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Term
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Definition
Properties: Strong Acid
Uses: A useful acid in many reactions - Can react with the pi bonds in alkenes and alkynes to make chlorinated compounds; may replace alcohol with Chloride group. |
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Term
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Definition
Properties: Strong Acid
Uses: Good acid for elimination reactions since the conjugate base is a very poor nucleophile - used in other reactions as a strong acid. |
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Term
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Definition
| Forms: Alkyl chlorides from alcohols; acid chlorides from carboxylic acids. |
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Term
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Definition
Properties: Very strong base but very poor nucleophile
Uses: Deprotonates alkynes to turn them into good nucleophiles. |
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Term
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Definition
| Uses: Reduces an Alkene to a terminal alcohol. |
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Term
| H2 + Metal Catalyst (Pd, Pt, Rh, or Ni) |
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Definition
| Uses: Reduces alkenes and Alkynes |
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Term
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Definition
| Uses: Reduces alkenes to alcohol with hydride shifts |
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Term
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Definition
| Uses: Oxidation of primary alcohols to aldehydes; oxidation of secondary alcohols to ketones. |
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Term
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Definition
Properties: Oxidizing Agent
Forms: Epoxides from alkenes |
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Term
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Definition
Properties: Lewis Acid
Uses: Promotes electrophilic aromatic substitution
Reaction: Bromonation and Friedel-Crafts |
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Term
| Phosphorus Trichloride (PCl3) |
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Definition
| Uses: Conversion of alcohols to alkyl chlorides - carboxylic acids to acid chlorides. |
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Term
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Definition
| Forms: Grignard Reagent from an alkane |
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Term
| Iron(III) Chloride (FeCl3) |
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Definition
Properties: Lewis acid
Uses: Promotes the chlorination of aromatic compounds
Reactions: Friedel-Crafts |
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Term
| Aluminium chloride (AlCl3) |
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Definition
Properties: Strong lewis acid
Uses: Promotes the chlorination of aromatic compounds
Reactions: Friedel-Crafts |
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Definition
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Definition
| Uses: Reduces an alkyne to a trans alkene through a radical mechanism |
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Definition
Properties: Very strong acid - poor nucleophilic conjugate base
Uses: Good acid for an elimination reaction |
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Term
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Definition
| Uses: Forms alkyl bromides from alcohols and acid bromides from carboxylic acids |
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Term
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Definition
Uses: Formation of alcohols from alkenes
Reaction: Hydroboration |
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Term
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Definition
Properties: Poisoned Pd catalyst
Uses: reduces an alkene to an alkyne
Forms: cis conformation |
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Term
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Definition
Properties: Strong acid
Uses: Will add -NO2 to aromatic compounds (usually in the presence of another acid such as H2O2) - will oxidize both primary alcohols and aldehydes into carboxylic acids |
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Term
| Grignard Reagents (R-Mg-X) |
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Definition
Properties: Extremely good nucleophiles and strong bases
NOTE: cannot have water present (until after Gringard reactant is used up) because it will react with reagent
Forms: An alcohol |
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Term
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Definition
| Uses: Converts alcohols to sulfonates (excellent leaving groups in elimination and substitution reactions) |
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Term
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Definition
Properties: Lewis Acid
Uses: Promotes bromination of aromatic compounds
Reactions: Friedel-Crafts |
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Term
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Definition
| Uses: Cleaves alkenes and alkynes to give carbonyl compounds |
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Term
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Definition
| Forms: Goes through an oxidation of an alcohol to create an aldehyde intermediate (PCC product) and continues to oxidize the alcohol to a carboxylic acid. |
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Term
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Definition
| In a conjugated alkene - a reaction with PBr3 will result in a reaction that goes between the reactants and the products because it is a Lewis Acid and will therefore yield a thermodynamic product because only the more energetically favored product w.ill be left |
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