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Common Reagents
Common Reactants For Organic Chemistry and their uses
29
Chemistry
Undergraduate 3
09/20/2014

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Term
Organolithium Reagents (R-Li)
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)
Term
Sodium Amide (NaNH2)
Definition
Properties: Very strong base, but poor nucleophile
Uses: Deprotonation of alkynes to make them excellent nucleophiles. (Used as an example in synthesis problem)
Term
Hydrochloric Acid (HCl)
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.
Term
Sulfuric Acid (H2SO4)
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.
Term
Thionyl Chloride (SOCl2)
Definition
Forms: Alkyl chlorides from alcohols; acid chlorides from carboxylic acids.
Term
Sodium Hydride (NaH)
Definition
Properties: Very strong base but very poor nucleophile
Uses: Deprotonates alkynes to turn them into good nucleophiles.
Term
1) BH3
2) NaOH, H2O2
Definition
Uses: Reduces an Alkene to a terminal alcohol.
Term
H2 + Metal Catalyst (Pd, Pt, Rh, or Ni)
Definition
Uses: Reduces alkenes and Alkynes
Term
H2 + H2O
Definition
Uses: Reduces alkenes to alcohol with hydride shifts
Term
PCC
Definition
Uses: Oxidation of primary alcohols to aldehydes; oxidation of secondary alcohols to ketones.
Term
mCPBA
Definition
Properties: Oxidizing Agent
Forms: Epoxides from alkenes
Term
AlBr3
Definition
Properties: Lewis Acid
Uses: Promotes electrophilic aromatic substitution
Reaction: Bromonation and Friedel-Crafts
Term
Phosphorus Trichloride (PCl3)
Definition
Uses: Conversion of alcohols to alkyl chlorides - carboxylic acids to acid chlorides.
Term
Mg/ THF
Definition
Forms: Grignard Reagent from an alkane
Term
Iron(III) Chloride (FeCl3)
Definition
Properties: Lewis acid
Uses: Promotes the chlorination of aromatic compounds
Reactions: Friedel-Crafts
Term
Aluminium chloride (AlCl3)
Definition
Properties: Strong lewis acid
Uses: Promotes the chlorination of aromatic compounds
Reactions: Friedel-Crafts
Term
MMPP
Definition
Forms: Epoxides
Term
Na, NH3
Definition
Uses: Reduces an alkyne to a trans alkene through a radical mechanism
Term
Tosic Acid (TsOH)
Definition
Properties: Very strong acid - poor nucleophilic conjugate base
Uses: Good acid for an elimination reaction
Term
Thionyl Bromide SOBr2
Definition
Uses: Forms alkyl bromides from alcohols and acid bromides from carboxylic acids
Term
1)BH3-THF
2) H2O2, NaOH
Definition
Uses: Formation of alcohols from alkenes
Reaction: Hydroboration
Term
Lindlar's Catalyst
Definition
Properties: Poisoned Pd catalyst
Uses: reduces an alkene to an alkyne
Forms: cis conformation
Term
Nitric Acid (HNO3)
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
Term
Grignard Reagents (R-Mg-X)
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
Term
Tosyl Chloride (TsCl)
Definition
Uses: Converts alcohols to sulfonates (excellent leaving groups in elimination and substitution reactions)
Term
Iron (III) Bromide FeBr3
Definition
Properties: Lewis Acid
Uses: Promotes bromination of aromatic compounds
Reactions: Friedel-Crafts
Term
Ozone (O3)
Definition
Uses: Cleaves alkenes and alkynes to give carbonyl compounds
Term
Jones Reagent
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.
Term
PBr3
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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