Chemistry 1506: Allied Health Chemistry 2. Section 3: Alchols, Phenols, Ethers, and Halides. Functional Groups with Single Bonds to Oxygen.
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1 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 1/21 Chemistry 1506: Allied Health Chemistry 2 Section 3: Alchols, Phenols, Ethers, and Halides Functional Groups with Single Bonds to Oxygen Outline SECTION 3.1 INTRODUCTION AND NOMENCLATURE OF ALCOHOLS...2 SECTION 3.2 ALCOHOL REACTIONS...5 SECTION 3.3 BIOLOGICAL ALCOHOLS...9 SECTION 3.4 AMINO ACIDS HAVING ALCOHOL CONTAINING SIDE CHAINS...10 SECTION 3.5 PHENOLS...11 SECTION 3.6 AMINO ACIDS HAVING PHENOL SIDE CHAINS...14 SECTION 3.7 ETHERS...15 SECTION 3.8 THIOLS, THIOETHERS, AND DISULFIDES...17 SECTION 3.9 AMINO ACIDS HAVING SULFUR CONTAINING SIDE CHAINS...18
2 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 2/21 Section 3.1 Introduction and Nomenclature of Alcohols Methanol "Wood alcohol", causes blindness CH 3 -OH Ethanol Oldest man made chemical (history of agriculture) "Grain alcohol" CH 3 -CH 2 -OH Made by sugar fermentation with yeast (wine, beer, gasoline) Made industrially by Ethene Hydration (H 2 O/H 2 SO 4 )
3 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 3/21 Isopropanol "rubbing alcohol" (CH 3 ) 2 CH-OH IUPAC Nomenclature Use anol suffix Number longest chain to include as many OH groups as possible Polyols (diol, triol, tetraol, etc.) Examples
4 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 4/21 Alcohol Classification Primary Alcohols, 1 Secondary Alcohols, 2 Tertiary Alcohols, 3 Properties Related to Water Intermolecular Hydrogen Bonding Mp and Bp Polar Solubility Biologically Active
5 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 5/21 Section 3.2 Alcohol Reactions Sources of Alcohol Reactivity Bond polarity of R-OH Weak acidity of R-OH Dehydration Elimination of water (i.e., H 2 O loss) Acid Catalyzed (H 2 SO 4 and heat) Generic Reaction Zaitsev's Rule Elimination proceeds to give the most substituted alkene Dehydration of 2-butanol
6 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 6/21 Oxidation Effects due to class of alcohol 3 vs. 2 vs. 1 Effects due to Oxidizing agent Strength "Generic" Oxidizing Agent, [O] CrO 3 / pyridine (pyr) Chromium trioxide poisoned oxidation K 2 Cr 2 O 7 /H 2 SO 4 Potassium Dichromate full strength oxidation
7 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 7/21 "Weak Oxidation" of 1 Alcohols Oxidation of Aldehydes "Strong Oxidation of 1 Alcohols
8 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 8/21 Oxidation of 2 Alcohols Failed Oxidation of 3 Alcohols
9 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 9/21 Section 3.3 Biological Alcohols Glycerol Component of Triglycerides Most common animal and vegetable fats Triol CH 2 (OH)-CH(OH)-CH 2 (OH)
10 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 10/21 Section 3.4 Amino Acids having Alcohol Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Serine R = CH 2 -OH Threonine R = CH(CH 3 )-OH
11 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 11/21 Section 3.5 Phenols Aromatic Alcohols Originally derived industrially from coal tar Generic Structure (Aromatic-OH) Properties Often unpleasant odors Intermolecular Hydrogen Bonding Mp and Bp Solubility Toxicity Acidity (cf. Alcohols)
12 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 12/21 Phenol (C 6 H 5 -OH) Cresol (ortho, meta, and para-methyl phenol)
13 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 13/21 Many Natural Products Lignins in wood Pulp mill effluent Aerobic oxidation "Trout test" Vanillin (1-OH, 2-OCH 3, 4-CHO)
14 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 14/21 Section 3.6 Amino Acids having Phenol Side Chains Amino Acid Generic AA = H 2 N-CHR-CO 2 H Tyrosine R = CH 2 -p-c 6 H 4 -OH
15 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 15/21 Section 3.7 Ethers R-O-R Structure Bond angles Physical Properties Mp and Bp vs. Alchols Polarity Hydrogen Bonding (cf. Alcohols and Water) Solubility Nomenclature Dialkyl Ether (two words) Alkyl Alkyl' Ether (three words) Chemical Reactivity Generally very low Used as Solvents
16 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 16/21 Diethyl Ether CH 3 -CH 2 -O-CH 2 -CH 3 "ether", ethyl ether Anaesthetic Made from grain alcohol and acid THF (tetrahydrofuran) Made from Oat husks, Quaker Oat Company Used to make specialty plastics (car dashboards) Ethylene Oxide Exceptionally reactive due to ring strain Medical sterilization MTBE (methyl tertiarybutyl ether)
17 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 17/21 Section 3.8 Thiols, Thioethers, and Disulfides Cf. Hydrogen Sulfide (H 2 S) Stink and Toxic Thiols (Mercaptans) R-S-H Pentanethiol (CH 3 CH 2 CH 2 CH 2 CH 2 -SH), skunk oil Thioethers R-S-R Disulfides R-S-S-R
18 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 18/21 Section 3.9 Amino Acids having Sulfur Containing Side Chains Amino Acids (Generic AA = H 2 N-CHR-CO 2 H) Cysteine (neutral polar) R = CH 2 -SH Cystine CH 2 -S-S-CH 2 bridge Methionine (non-polar) R = CH 2 CH 2 -S-CH 3
19 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 19/21 Index of Topics and Vocabulary (CH 3 ) 2 CH-OH , 6 1 Alcohols , , 6 Acid Catalyzed... 5 acidity... 5 Acidity Aerobic oxidation agriculture... 2 Alcohol Classification... 4 Alcohol Reactions... 5 Alcohols... 11, 15 Aldehydes... 7 Amino Acid Amino Acids... 10, 18 Amino Acids having Alcohol Containing Side Chains Amino Acids having Phenol Side Chains Amino Acids having Sulfur Containing Side Chains Anaesthetic anol... 3 Aromatic Alcohols beer... 2 Biological Alcohols... 9 Biologically Active... 4 blindness... 2 Bond angles Bond polarity... 5 Bp... 4, 11, 15 C 6 H 5 -OH...12 CH 2 (OH)-CH(OH)-CH 2 (OH)...9 CH 3 -CH 2 -OH...2 CH 3 -OH...2 Chromium trioxide...6 coal tar...11 Cresol...12 CrO Cysteine...18 Cystine...18 Dehydration...5 Dialkyl Ether...15 Diethyl Ether...16 diol...3 Disulfides...17 Elimination of water...5 Ethanol...2 Ethene...2 ether...16 Ethers...15 ethyl ether...16 Ethylene Oxide...16 Failed Oxidation of 3 Alcohols8 fermentation...2 full strength oxidation...6 Glycerol...9 Grain alcohol...2 H 2 O/H 2 SO H 2 S...17 H 2 SO Hydration...2 Hydrogen Bonding...4, 11, 15 Hydrogen Sulfide...17
20 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 20/21 industrially... 2 Intermolecular... 4, 11 Introduction and Nomenclature of Alcohols... 2 Isopropanol... 3 IUPAC... 3 K 2 Cr 2 O Lignins Mercaptans meta Methanol... 2 Methionine methyl tertiarybutyl ether most substituted alkene... 5 Mp... 4, 11, 15 MTBE Natural Products Nomenclature... 3, 15 Oat husks Oldest man made chemical... 2 ortho Oxidation... 6 Oxidation of 2 Alcohols... 8 Oxidizing agent... 6 para Pentanethiol Phenol Phenols plastics poisoned oxidation... 6 Polar... 4 polarity... 5 Polarity Polyols... 3 Potassium Dichromate... 6 Primary Alcohols...4 Properties...4, 11, 15 Proteins...10 Pulp mill effluent...13 pyr...6 pyridine...6 Quaker Oat Company...16 Reactivity...5, 15 ring strain...16 rubbing alcohol...3 Secondary Alcohols...4 Serine...10 skunk oil...17 Solubilit...15 Solubility...4, 11 Solvents...15 sterilization...16 Strong Oxidation of 1 Alcohols...7 sugar...2 Tertiary Alcohols...4 tetrahydrofuran...16 tetraol...3 THF...16 Thioethers...17 Thiols...17 Thiols, Thioethers, and Disulfides...17 Threonine...10 Triglycerides...9 triol...3 Triol...9 Trout test...13 Tyrosine...14 unpleasant odors...11
21 Chemistry 1506 Dr. Hunter s Class Section 3 Notes - Page 21/21 Vanillin Water... 4, 15 Weak acidity... 5 Weak Oxidation... 7 wine...2 Wood alcohol...2 yeast...2 Zaitsev's Rule...5
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