Solvents

 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
 FAVORABLE FOR SN1 RXNS

 Polar Aprotic Solvent  is a solvent that cannot donate Hydrogen.

 These are essential for Rxns which use strong bases, such as Grignard Reagents, or N-
Butyllithium.
 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.
 FAVORABLE FOR SN2 RXNS
 Solvent Chemical Formula Boiling point Dielectric constant Density Dipole moment
(D)Non-Polar Solvents
Hexane CH3-CH2-CH2-CH2-CH2-CH3 69 °C 2.0 0.655 g/ml 0.00 D
Benzene C6H6 80 °C 2.3 0.879 g/ml 0.00 D
Toluene C6H5-CH3 111 °C 2.4 0.867 g/ml 0.36 D
1,4-Dioxane /-CH2-CH2-O-CH2-CH2-O-\ 101 °C 2.3 1.033 g/ml 0.45 D
Chloroform CHCl3 61 °C 4.8 1.498 g/ml 1.04 D
Diethyl ether CH3CH2-O-CH2-CH3 35 °C 4.3 0.713 g/ml 1.15 D

Polar Aprotic Solvents

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

Polar Protic Solvents

Formic acid H-C(=O)OH 101 °C 58
n-Butanol CH3-CH2-CH2-CH2-OH 118 °C 18
Isopropanol (IPA) CH3-CH(-OH)-CH3 82 °C 18
n-Propanol CH3-CH2-CH2-OH 97 °C 20
Ethanol CH3-CH2-OH 79 °C 30
Methanol CH3-OH 65 °C 33
Acetic acid CH3-C(=O)OH 118 °C 6.2
Water H-O-H 100 °C 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)H-
C(=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-CH2-
OH79 °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