Term
|
Definition
| These reagents are all relatively Bronsted acidic (they contain one or more hydrogen atoms that can be lost as a proton in a transfer reaction with water). |
|
|
Term
|
Definition
| A highly polar substance, it stabilizes ionic intermediates. Fairly nucleophilic. A strong hydrogen-bond donor and acceptor, considered a Bronsted acid and incompatible with most carbanions. |
|
|
Term
| Methanol (MeOH), Ethanol (EtOH), Isopropanol (i-PrOH), and Tert-Butanol (t-BuOH) |
|
Definition
| Highly protic solvents. Miscible in water, thus can be co-solvents with water. Bronsted acids. Primary and secondary alcohols are good nucleophiles. In the presence of strong acids (HCl, HNO3), tertiary alcohols and some secondary alcohols may ionize forming a carbocation. |
|
|
Term
| Acetic Acid (AcOH, CH3CO2H) |
|
Definition
| Polar Protic Solvent. Weak Bronsted acid. Can provide a good polar environment to stabilize ionic reactive intermediates generated by stronger acids. Somewhat nucleophilic, will attack strongly electrophilic atoms and cationic intermediates to form an acetate ester product. |
|
|
Term
|
Definition
| Highly polar, but do not behave as Bronsted acids towards water. Frequently used for SN2 displacement ractions where they stabalize the charge-separation that occurs in the transition state. Hydrogen-bond acceptors, but not hydrogen-bond donors. |
|
|
Term
|
Definition
| Polar aprotic solvent. A good solvent for medium-to-high polarity organic molecules and some hydrocarbons as well. Often used for SN2 displacement reactionswhere a soluble salt is the source of the nuclephile, but the leaving group forms and insoluble salt. |
|
|
Term
| Dimethylsulfoxide (DMSO, CH3S(O)CH3) |
|
Definition
| Polar aprotic solvent. Disolves most organics and most inorganic salts. Good solvent for SN2 displacement. Incompatible with very strong nuclephiles or bases. Somewhat nucleophilic, if there is no better leaving group around, DMSO will displace good leaving groups. |
|
|
Term
N,N-Dimethylformamide
(DMF, HC(O)N(CH3)2) |
|
Definition
| Behaves like DMSO, but is not significantly nucleophilic. |
|
|
Term
|
Definition
| Medium polarity solvents. Dissolve organics but do not dissolve common salts. Typically Grignard reactions, reactions of organolithium reagents or LDA, or reactions with a metallic cation reagent. Lewis bases and not Bronsted acids. |
|
|
Term
| Diethyl Ether (Ether, Et2O, CH3CH2OCH2CH3) |
|
Definition
| Ether. Disolves many organic materials, but is only slightly soluable in water. A weak Bronsted base, and can be protonated by anhydrous HCl or H2SO4. Fairly good Lewis base and can solvate some metallic reagents (although not ionic salts). |
|
|
Term
| Tetrahydrofuran (THF, [image], C4H8O) |
|
Definition
| Ether. Dissolves almost any organic molecule and a large number of inorganic reagents. Solvates Lewis acids. Weak Bronsted bases, only protonated by very stron Bronsted acids. Miscible in water. |
|
|
Term
|
Definition
| Moderately polar. Denser than water. Not flammable. |
|
|
Term
| Dichloromethane (methylene chloride, CH2Cl2) |
|
Definition
| Chlorinated Solvent. Immiscible with water. Dissolves mid- to low-polarity organics very well. Dissolves common inorganic Lewis acids. Stable to weak and medium Bronsted bases, but incompatible with carbanions and strong organic bases. |
|
|
Term
|
Definition
| Chlorinated Solvent. Chloroform-d, its deuterated form, is the most widely used solvent for organic NMR spectrometry. Cannot be exposed to bases even as strong as hydroxide since it is easily converted to dichlorocarbene by and α-elimination reaction. |
|
|
Term
|
Definition
Neither acidic or basic in either the Lewis or Bronsted sense. Will only dissolve low polarity organics.
Common aliphatic solvents: pentene, hexanes, iso-octane, and decalin
Common aromatic solvents: benzene, toluene, and xylenes |
|
|
Term
|
Definition
| Bronsted and Lewis bases. Reactions that generate protons are frequently performed in the presence of amine bases. |
|
|
Term
| Triethylamine (Et3N, (CH3CH2)3N) |
|
Definition
| Amine solvent. Miscible with water and most organics. Often used as a reagent or co-solvent. |
|
|
Term
| Pyridine (Pyr,[image], C5H5N) |
|
Definition
| Amine solvent. Quite nucleophilic. Very soluable in water. |
|
|
Term
| Ethyl Acetate (EtOAc, CH3CO2CH2CH3) |
|
Definition
| Frequently used in extractions and in chromatography. More polar than ether but less polar than THF. Only slightly soluable in water. |
|
|
Term
| Acetonitrile (Methyl cyanide, CH3CN) |
|
Definition
| Highly polar solvent. A good hydrogen bond acceptor, but not a hydrogen bond donor. The nitrogen is very weakly basic but can be quite nucleophilic. Miscible with water. Frequently used as a solvent for SN2 reactions. |
|
|
