Chapter 8 - Chapter 8. Introduc1on to Alkyl halides,...

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Unformatted text preview: Chapter 8. Introduc1on to Alkyl halides, alcohols, ethers, thiols, and sulfides Alcohol: with hydroxy group(s) Nomenclature: alkyl halides Common nomenclature Common names that need to be memorized Subs1tu1ve nomenclature: alkyl halides Common Nomenclature: alcohols and thiols Subs1tu1ve nomenclature of alcohols and thiols Common nomenclature of ethers and sulfides Ethers Sulfides Subs1tu1ve nomenclature: ether Heterocyclic nomenclature Structures of ethers, alcohols, thiols and sulfides Physical proper1es: molecular polarity Boiling points of ethers Boiling points of alkyl halides Boiling points of alcohols Solubility: like dissolves like Solubility in water: Hydrophobic: “hydro ­” (water) + “phobos” (fear) Hydrophilic: “hydro ­” (water) + “philia” (friendship) Amphipathic: “amphis” (both) + “philia” (friendship) insoluble Soluble Solvents Pro1c vs. apro1c: A pro1c solvent consists of molecules that can act as H ­bond donors (e.g. water, alcohols) Apro1c solvents cannot act as hydrogen ­bond donors are called apro1c solvents (e.g. ether, methylene chloride) Polar vs. apolar: A polar solvent has a high dielectric constant An apolar solvent has low dielectric constant Donor vs. nondonor: Donor solvents consist of molecules that can donate unshared electron pairs (i.e. Lewis bases, e.g. ether, THF and methanol); Nondonor solvents cannot act as Lewis bases (e.g. pentane, benzene) Hydrogen bonding enhances solubility Solubility of ionic compounds Solubility determining factors for ionic compounds: 1.  Charge ­dipole interac1ons 2.  Hydrogen ­bonding interac1ons 3.  Donor interac1ons Cellular membrane Crown ether [18] ­crown ­6 either complex with a potassium ion 18 ­crown ­6 ­potassium Molecular Recogni1on: Host ­Guest Chemistry The Nobel Prize in Chemistry 1987 "for their development and use of molecules with structure ­specific interac1ons of high selec1vity” Donald J. Cram 1/3 of the prize USA UCLA, USA Jean ­Marie Lehn 1/3 of the prize France Université Louis Pasteur Charles J. Pedersen 1/3 of the prize USA Du Pont Wilmington, Acidity of alcohols Polar effects on alcohol acidity Roles of the solvent in alcohol acidity Acidity of thiols Thiols form insoluble mercap1des with heavy ­metal ions Basicity of alcohols Produc1on of alcohols Basicity of ethers Grignard The Nobel Prize in Chemistry 1912 "for the discovery of the so ­called Grignard reagent, which in recent years has greatly advanced the progress of organic chemistry" Victor Grignard France Nancy University Nancy, France b. 1871 d. 1935 Grignard reagents Protonolysis of Grignard reagents Organolithium reagents Forma1on of Grignard reagents Industrial prepara1on of alkyl halides Freon catalyzes the destruc1on of ozone Key Points •  •  •  •  •  •  •  •  •  •  •  •  Func1onal groups in alkyl halides, alcohols, ethers, thiols, and sulfides; Nomenclatures: common nomenclatures for special compounds and subs1tu1ve nomenclature; Iden1fy principal group (appendix I); Boiling points of ethers, alkyl halides, and alcohols (high b.p. due to H ­bonding); Solvents: pro1c/apro1c, polar/apolar (different defini1on to polarity of molecules), donor/nondonor; Solubility: “like dissolves like”; Solubility of ionic compounds in water; stabilizing factors (charge ­dipole interac1ons, hydrogen ­bonding, donor interac1ons); Crown ether and applica1ons; Acidity of alcohols (pKa trend, polar effects, roles of solvents); Basicity of alcohols and ethers; Grignard reagents and their applica1ons; Protonolysis of Grignard reagents; Organolithium reagetns (similarity and dissimilarity with Grignard reagents) ...
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