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CHM247H1 (26)
Chapter 17

Alcohol - Lecture and Textbook Notes Chapter 17

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Cecilia Kutas

CHM247H1 Jasmyn Lee Chapter 17: Alcohol and Phenol  R-OH and ar-OH  In alcohols C(sp )-OH  In phenols C(sp )-OH Complex alcohols OH cholesterol most steroids function as hormonesols & phenols 3  Most(chemical messengers) hormones (chemical messengers) More complex alcohols OH OH OH OH OH cholesterol O O O O O O O HO HO HO O OH OH HO O OH OH OH testosterone(development of OH O cellulose HO male sexual characteristics) O OH O O OHO O HO OH OH OH OH O OH O O HO O O HO Amylose OH O progesterone HO OH (a form of starch)O Hydrocortisone OH alcohols & phenolsity control) 4 glucose alcohols & phenols OH 5 (control inflammation) O  Carbolic Acid (phenol) was one of the first Antiseptics used in surgery R OCH R2 R O- Na+ O R' OR R-O-Tos R-O-Si(CH )3 3 RX alkene R OH RCOOH, RCHO  Physical properties of alcoholsls & phenols 7 1 CHM247H1 Jasmyn Lee o Hydrogen Bonding  ~20 kJ/mol  Leads to higher boiling points, melting points than alkanes of similar molecular weight o Alcohols are Amphoteric -  Acidity R-O-H + B:⇌ R-O + BH  Hydride (H: ), amide ( :NH )2can remove alcohol H  pKa CH C3 OH2= 15.9; (pKa H O = 25.7)  Basicity R-O-H + HCl ⇌ R-OH + 2l - Influence of chemical structure on acid strength Formula pKa HCl -7 strong CH 3O H 2 4.8 (CF 3 3OH 5.4 C6H 5H 9.9 CH OH 15.5 3 H 2 15.7 CH 3H OH2 15.9 (CH 3 2HOH 17 (CH ) COH 18 weak 3 3 alcohols & phenols 10 Spectroscopy of Alcohols IR Spectrum of an Alcohol IR Spectrum of a Phenol alcohols & phenols 11 alcohols & phenols 12  IR o Characteristic broad, strong O-H stretch  3300 – 3600 cm -  C-O near 1200 cm -1 -1 o IR of a phenol shows aromatic absorption O-H  3300-3600 cm  C=C at 1600 cm -1  H NMR o R-O-H often appears as a broad singlet  1-5 δ (depending on concentration) o Often do not see spin-spin splitting due to rapid proton exchange o R-O-H ⇌(H+) R-O-H o CH 3OH appears ~4δ o PhOH appears ~3.8δ 2 CHM247H1 Jasmyn Lee C 8 O 10 -1 IR: 3500 cm Nomenclature Use suffix –OL, name as alcohol if highest 5 priority functional group on molecule 1H 1H OH (S)-3-chloro-1-pentanol Nomenclature Cl Use suffix –OL, name as alcohol if highest Nomenclature  Use suffix –OL, name as alcohol if highest priority functional group on molecule OH HO (S)-3-chloro-1-pentanol (E)-(S)-5-ethylhept-3-en-2-ol Cl alcohols & phenols (E/Z) 15sted before (R/S) alcohols & phenols 16 Preparation of Alcohols  Alkene Oxymercuration HO (E)-(S)-5-ethylhept-3-en-2-ol (E/Z) listed before (R/S)  Alkene Hydroborationcohols & phenols 16 Alkene hydroxylation OH  AlAlkene hydroxylation SYN addition OH OH SYN addition OH Alkene hydroxylation OH Alkene hydroxylation ANTI addition OH 21. RCO H2 O 3 OH ANTI addition  Reactions of C2. NaOH, H Oke Compounds With Grignard Reagent 2 OH alcohols & phenols 18 alcohols & phenols 18 3 CHM247H1 Reac%ons)of)Carbonyl)&)Like)Cmpds)with)Grignard)Reagent) Jasmyn Lee O 1. RMgX, ether C + R CH2OH H H 2. 3 O formaldehyde 1 alcoholalcohol O H 1. RMgX, ether R C OH C + R H 2. 3 O R aldehyde s2 alcoholalcohol O 1. RMgX, anh. etheR OH + 2. 3 O o epoxide alcohols & phenolsohol 19 O O H C 1. RMgX, ether C R R 2. H O R R 3 R ketone tertiary alcohol O OH 1.RMgX, ether C C R OR 2. H O R R 3 R esters tertiary alcohol (react with 2 equivalents of Grignard)  Reduction of Carbonyl Compounds (as in lab V) o Aldehydes and Ketoneshenols 20 O O H C 1. NaB4 , EtOH + C R H 2.3H O R H H aldehyde primary alcohol O 1.NaBH , EtOH OH 4 C + 2. 3 O C R R R R H ketone secondary alcohol alcohols & phenols 21 4 Must use more reactive LiAlH to CHM247H1 4 Jasmyn Lee o Ester and Carboyxlic Acidsboxylic acids  Must use more reactive 4iAlH to reduce esters and carboxylic acids O OH 1. LiA4H , ether C + C + R'OH R OR' 2. 3 O R H H ester primary alcohol O OH C 1.iAl4 ether C R OH + R H 2.3H O H Dehydration of alcoholsid primary alcohol alcohols & phenols 22 Dehydration of AlcoholsD  Works best on 3° alcohols, requires concentrated acid, heat OH H2SO 4 D works best on 3 alcohols, works bestrequires concentrated acid, heat  Phosphorous oxychlorioe works on 2° or 3° alcohols, need mild (low temp) and basic conditions works besrequires concentrated acid, heat OH POCl 3 OH POCl3 Mechanism of POCl pyridineion 3 _ phosphorus oxychloride works on 2 or 3 alcohols, POCl worneeds mild (low temp.) and basic conditions 3 phosphoOus oxychloride works +n 2Por 3 alcohols, POCl 3orneeds mild (low temp.) and Clsic conditions P alcohols & phenols Cl 23 Cl Cl Cl N H O O + P Cl Cl O O P Cl Cl H N alcohols & phenols 24 Alkyl Halide Formationformation OH HCl Cl (SN1) ether 5 for 2 /1 alcohols, use SOCl or PBr CHM247H1 for 2 /1 alcohols, use SOCl or PBr Jasmyn Lee 2 3  For 2°/1° alcohols2 use3SOC
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