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Aprotic and Protic Solvents

Aprotic and Protic Solvents

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Published by: looksmart111 on Nov 22, 2010
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Polar Protic solvents is a solvent that has a hydrogen atom bound to an oxygen as in a hydroxyl group or a nitrogen as in an amine group. Any Molecular Solvent which contains dissociable H+ is called a protic solvent. The Molecules of such a solvent can donate a H+ (proton). Solvents that share ion dissolving power with aprotic solvents but have an acidic hydrogen. These solvents have High Dielectric constants and High Polarity. Examples are Water, Methanol, Ethanol, Formic acid, Hydrogen fluoride and Ammonia o Hydrogen Bonding o Solvents with an Acidic Hydrogen (Very weak Acids) o Solvents able to stabilize ions  Cations by unshared free electron pairs  Anions by hydrogen bonding Polar Aprotic Solvent

y y y is a solvent that cannot donate Hydrogen. These are essential for Rxns which use strong bases, such as Grignard Reagents, or NButyllithium. Solvents that share ion dissolving power with protic solvents but lack an Acidic Hydrogen. Intermediate Dielectric constant and Polarity o Do Not!!! Display Hydrogen bonding o Solvents lack an Acidic Hydrogen o Solvents are able to stabilize Ions Examples are Dimethyl Sulfoxide, Dimethlyformamide, Dioxane, hexamethylphosphorotriamide, Tetrahydrofuran.



Hexane Benzene Toluene 1,4-Dioxane Chloroform Diethyl ether

Chemical Formula
CH3-CH2-CH2-CH2-CH2-CH3 C6H6 C6H5-CH3 /-CH2-CH2-O-CH2-CH2-O-\ CHCl3 CH3CH2-O-CH2-CH3

Boiling point Dielectric constant
69 °C 80 °C 111 °C 101 °C 61 °C 35 °C 2.0 2.3 2.4 2.3 4.8 4.3

0.655 g/ml 0.879 g/ml 0.867 g/ml 1.033 g/ml 1.498 g/ml 0.713 g/ml

Dipole moment
0.00 D 0.00 D 0.36 D 0.45 D 1.04 D 1.15 D

(D)Non-Polar Solvents

Polar Aprotic Solvents
Dichloromethane (DCM) Tetrahydrofuran (THF) Ethyl acetate Acetone Dimethylformamide (DMF) Acetonitrile (MeCN) Dimethyl sulfoxide (DMSO) CH2Cl2 /-CH2-CH2-O-CH2-CH2-\ CH3-C(=O)-O-CH2-CH3 CH3-C(=O)-CH3 H-C(=O)N(CH3)2 CH3-C N CH3-S(=O)-CH3 40 ° C 66 °C 77 °C 56 °C 153 °C 82 °C 189 °C 9.1 7.5 6.0 21 38 37 47

Polar Protic Solvents
Formic acid n-Butanol Isopropanol (IPA) n-Propanol Ethanol Methanol Acetic acid Water H-C(=O)OH CH3-CH2-CH2-CH2-OH CH3-CH(-OH)-CH3 CH3-CH2-CH2-OH CH3-CH2-OH CH3-OH CH3-C(=O)OH H-O-H 101 °C 118 °C 82 °C 97 °C 79 °C 65 °C 118 °C 100 °C 58 18 18 20 30 33 6.2 80

SolventChemical FormulaBoiling pointDielectric constantDensityDipole moment (D)Non-Polar SolventsHexaneCH3-CH2-CH2-CH2-CH2-CH369 °C2.00.655 g/ml0.00 DBenzeneC6H680 °C2.30.879 g/ml0.00 DTolueneC6H5-CH3111 °C2.40.867 g/ml0.36 D1,4-Dioxane/-CH2-CH2-O-CH2-CH2-O\101 °C2.31.033 g/ml0.45 DChloroformCHCl361 °C4.81.498 g/ml1.04 DDiethyl etherCH3CH2-O-CH2-CH335 °C4.30.713 g/ml1.15 DPolar Aprotic SolventsDichloromethane (DCM)CH2Cl240 °C9.11.3266 g/ml1.60 DTetrahydrofuran (THF)/-CH2-CH2-O-CH2-CH2-\66 °C7.50.886 g/ml1.75 DEthyl acetateCH3-C(=O)-O-CH2-CH377 °C6.00.894 g/ml1.78 DAcetoneCH3-C(=O)-CH356 °C210.786 g/ml2.88 DDimethylformamide (DMF)HC(=O)N(CH3)2153 °C380.944 g/ml3.82 DAcetonitrile (MeCN)CH3-C N82 °C370.786 g/ml3.92 DDimethyl sulfoxide (DMSO)CH3-S(=O)-CH3189 °C471.092 g/ml3.96 DPolar Protic SolventsFormic acidH-C(=O)OH101 °C581.21 g/ml1.41 Dn-ButanolCH3-CH2-CH2-CH2-OH118 °C180.810 g/ml1.63 DIsopropanol (IPA)CH3-CH(-OH)-CH382 °C180.785 g/ml1.66 Dn-PropanolCH3-CH2-CH2-OH97 °C200.803 g/ml1.68 DEthanolCH3-CH2OH79 °C300.789 g/ml1.69 DMethanolCH3-OH65 °C330.791 g/ml1.70 DAcetic acidCH3-C(=O)OH118 °C6.21.049 g/ml1.74 DWaterH-O-H100 °C801.000 g/ml1.85 D

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