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Structure and Molecular Properties

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Presentation on theme: "Structure and Molecular Properties"— Presentation transcript:

1 Structure and Molecular Properties
Summer 2012

2 Overview Syllabus ChemDraw Structures and intermolecular forces

3 Intermolecular Forces and Physical Properties
Virtual ChemBook, Elmhurst College

4 Solvents and Boiling Points
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

5 Boiling Point Trend: Mass
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC  74 amu 85 amu 58 amu 65 amu  32 amu  72 amu  hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC 86 amu  88 amu  46 amu  41 amu  18 amu  toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC  92 amu 79 amu  60 amu  73 amu  78 amu 

6 Intermolecular Forces
Hydrogen bonding Acceptor/donor Dipole/dipole Dipole/induced dipole Induced dipole/induced dipole Also called London dispersion forces VDWs Forces

7 H-Bond Donor, Acceptor, Neither, or Both
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

8 Polar Protic, Polar Aprotic, Nonpolar
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

9 London Forces in Nonpolar Solvents
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

10 General Principles If molecules are about the same mass
H-bonding > Dipole-dipole > Induced dipole Induced dipole is weakest interaction, but as surface area increases, cumulative effect can overcome stronger IMF Strategy for predicting relative boiling points

11 Solubility “Like dissolves like” Based on IMF

12 Miscibility and Density
Miscibility spectrum Density Organics (0.7 g/mL) Aqueous (1.0 g/mL) Halogenated (1.3 g.mL)

13 Miscibility with Water
Ether (diethyl ether) Dichloromethane (methylene chloride) acetone methanol Tetrahydrofuran (THF) 35 oC 40 oC 56 oC 65 oC 66 oC hexanes Ethyl acetate (EtOAC) ethanol acetonitrile water 69 oC 77 oC 78 oC 82 oC 100 oC toluene Pyridine (pyr) Acetic acid Dimethyl formamide (DMF) Dimethylsulfoxide (DMSO) 111 oC 115 oC 118 oC 153 oC 189 oC

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