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Page 1 Chapter 11: Alcohols and Ethers • Alcohols and Ethers: Structure and Properties (Sections 11.1-2) • Important Alcohols and Ethers (Section 11.3) • Synthesis of Alcohols from Alkenes (Section 11.4; Chapter 8) • Reactions of Alcohols (Section 11.5) • Old Acid Base Stuff (Section 11.6, Chapter 3) • Alcohols into Alkyl Halides (Section 11.7) • Alcohol Reactions w/ HX (Section 11.8) • Alcohol Reactions w/ PBr 3 , SOCl 2 (Section 11.9) • Alcohol Derivatives as Leaving Groups (Section 11.10) • Synthesis of Ethers (Section 11.11) • Reactions of Ethers (Section 11.12) • Epoxides: Synthesis and Opening (Sections 11.13 and 11.14) • Anti 1,2 Dihydroxylation of Alkenes (Section 11.15) Page 2 Chapter 11: Alcohols and Ethers • Alcohols and Ethers: Structure and Properties (Sections 11.1-2) • Important Alcohols and Ethers (Section 11.3) • Synthesis of Alcohols from Alkenes (Section 11.4; Chapter 8) • Reactions of Alcohols (Section 11.5) • Old Acid Base Stuff (Section 11.6, Chapter 3) • Alcohols into Alkyl Halides (Section 11.7) • Alcohol Reactions w/ HX (Section 11.8) • Alcohol Reactions w/ PBr 3 , SOCl 2 (Section 11.9) • Alcohol Derivatives as Leaving Groups (Section 11.10) • Synthesis of Ethers (Section 11.11) • Reactions of Ethers (Section 11.12) • Epoxides: Synthesis and Opening (Sections 11.13 and 11.14) • Anti 1,2 Dihydroxylation of Alkenes (Section 11.15) Alcohols: General Nomenclature OH OH OH OH OH OH H OH OH OH OH t Bu Methanol Ethanol 2-Propanol 2-methyl-2-propanol Benzyl alcohol 2-Propenol 2-Propynol Phenol m-Ethylphenol p-tert-Butylphenol Page 3 Chapter 11: Alcohols and Ethers • Alcohols and Ethers: Structure and Properties (Sections 11.1-2) • Important Alcohols and Ethers (Section 11.3) • Synthesis of Alcohols from Alkenes (Section 11.4; Chapter 8) • Reactions of Alcohols (Section 11.5) • Old Acid Base Stuff (Section 11.6, Chapter 3) • Alcohols into Alkyl Halides (Section 11.7) • Alcohol Reactions w/ HX (Section 11.8) • Alcohol Reactions w/ PBr 3 , SOCl 2 (Section 11.9) • Alcohol Derivatives as Leaving Groups (Section 11.10) • Synthesis of Ethers (Section 11.11) • Reactions of Ethers (Section 11.12) • Epoxides: Synthesis and Opening (Sections 11.13 and 11.14) • Anti 1,2 Dihydroxylation of Alkenes (Section 11.15) Alcohols: General Nomenclature OH OH OH OH OH OH H OH OH OH OH t Bu Methanol Ethanol 2-Propanol 2-methyl-2-propanol Benzyl alcohol 2-Propenol 2-Propynol Phenol m-Ethylphenol p-tert-Butylphenol Substitution in Benzene Rings X X X X X X para meta ortho Use para/meta/ortho Designations to Describe Substituent Orientation in Disubstituted Benzene Rings, Just as in the Phenol Examples from Previous Slide Page 4 Chapter 11: Alcohols and Ethers • Alcohols and Ethers: Structure and Properties (Sections 11.1-2) • Important Alcohols and Ethers (Section 11.3) • Synthesis of Alcohols from Alkenes (Section 11.4; Chapter 8) • Reactions of Alcohols (Section 11.5) • Old Acid Base Stuff (Section 11.6, Chapter 3) • Alcohols into Alkyl Halides (Section 11.7) • Alcohol Reactions w/ HX (Section 11.8) • Alcohol Reactions w/ PBr 3 , SOCl 2 (Section 11.9) • Alcohol Derivatives as Leaving Groups (Section 11.10) • Synthesis of Ethers (Section 11.11) • Reactions of Ethers (Section 11.12) • Epoxides: Synthesis and Opening (Sections 11.13 and 11.14) • Anti 1,2 Dihydroxylation of Alkenes (Section 11.15) Alcohols: General Nomenclature OH OH OH OH OH OH H OH OH OH OH t Bu Methanol Ethanol 2-Propanol 2-methyl-2-propanol Benzyl alcohol 2-Propenol 2-Propynol Phenol m-Ethylphenol p-tert-Butylphenol Substitution in Benzene Rings X X X X X X para meta ortho Use para/meta/ortho Designations to Describe Substituent Orientation in Disubstituted Benzene Rings, Just as in the Phenol Examples from Previous Slide Alcohols and Ethers: Physical Properties • Properties of Ethers Similar to Alkanes of Like Masses ? Diethyl ether (MW=74); Pentane (MW=72) ? Diethyl ether (BP=34.6 °C); Pentane (BP=36 °C) • Alcohols Boil Much Higher than Comparable Ethers/Alkanes • Related to Hydrogen Bonding of Alcohols (See Chapter 4) • Alcohols form Hydrogen Bonding Networks w/ one Another • Ethers Cannot Hydrogen Bond w/ one Another • Ethers CAN H-Bond w/ H 2 O and Alcohols (Soluble in These) Properties of Some Alcohols/Ethers in Tables 11.1 and 11.2 Page 5 Chapter 11: Alcohols and Ethers • Alcohols and Ethers: Structure and Properties (Sections 11.1-2) • Important Alcohols and Ethers (Section 11.3) • Synthesis of Alcohols from Alkenes (Section 11.4; Chapter 8) • Reactions of Alcohols (Section 11.5) • Old Acid Base Stuff (Section 11.6, Chapter 3) • Alcohols into Alkyl Halides (Section 11.7) • Alcohol Reactions w/ HX (Section 11.8) • Alcohol Reactions w/ PBr 3 , SOCl 2 (Section 11.9) • Alcohol Derivatives as Leaving Groups (Section 11.10) • Synthesis of Ethers (Section 11.11) • Reactions of Ethers (Section 11.12) • Epoxides: Synthesis and Opening (Sections 11.13 and 11.14) • Anti 1,2 Dihydroxylation of Alkenes (Section 11.15) Alcohols: General Nomenclature OH OH OH OH OH OH H OH OH OH OH t Bu Methanol Ethanol 2-Propanol 2-methyl-2-propanol Benzyl alcohol 2-Propenol 2-Propynol Phenol m-Ethylphenol p-tert-Butylphenol Substitution in Benzene Rings X X X X X X para meta ortho Use para/meta/ortho Designations to Describe Substituent Orientation in Disubstituted Benzene Rings, Just as in the Phenol Examples from Previous Slide Alcohols and Ethers: Physical Properties • Properties of Ethers Similar to Alkanes of Like Masses ? Diethyl ether (MW=74); Pentane (MW=72) ? Diethyl ether (BP=34.6 °C); Pentane (BP=36 °C) • Alcohols Boil Much Higher than Comparable Ethers/Alkanes • Related to Hydrogen Bonding of Alcohols (See Chapter 4) • Alcohols form Hydrogen Bonding Networks w/ one Another • Ethers Cannot Hydrogen Bond w/ one Another • Ethers CAN H-Bond w/ H 2 O and Alcohols (Soluble in These) Properties of Some Alcohols/Ethers in Tables 11.1 and 11.2 Important Alcohols and Ethers • Methanol (CH 3 OH) • Often Called Wood Alcohol (Distilled From Wood) • Prepared Now via Catalytic Hydrogenation Reactions • Ethanol (CH 3 CH 2 OH) • Made Through Fermentation of Sugars, in Alcoholic Drinks • Common Solvent in Organic Labs (Absolute Ethanol) • Ethylene Glycol (HOCH 2 CH 2 OH) • Good Antifreeze: Low MW, High Boiling Point (197 °C) • Diethyl Ether (CH 3 CH 2 OCH 2 CH 3 ) • Low Boiling Point, Volatile, Highly Flammable Liquid • One of First Uses was as Surgical Anesthetic • Watch Out for Old Ether Containers (Peroxides!!)Read More
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