Chapter 19_Class Notes - Chapters19and25:Aldehydes,Ketones...

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Chapters19and25:Aldehydes,Ketones andCarbohydrates 1 O (R)-Carvone (Spearmint flavor)
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Chapter19:AldehydesandKetones ChemicalandEngineeringNews, pp 26,July2,2012;pp 45,July30,2012. Vanillin: Anaturalvanillaextract Usedincandy,dairyproducts,and perfumes O H OCH 3 HO Review: Whatisthenameofthissubstituent? Whatisthechemicalshiftofthe protonsin 1 HNMR Wheredoesthecarbonappearin 13 C NMR? H 3 CO HO O O OCH 3 OH Curcumin: Fromtherootstalkofturmericplant Exhibitsantioxidant,anti‐inflamatory activity;potentialcureforalzheimer’s disease 2
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IUPACofAldehydes Rules: Theparentchainmustcontainthe“CHO”(aldehyde)group The“CHO”groupisusuallyassigned#1 Replacethe“ e ”inthealkanenamewith“‐ al Examples H H O H O H O IUPACname: Commonname: (acceptedbyIUPAC) 3
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I Ifthealdehydeisattachedtoaring,thecompoundisnamedby adding“carbaldehyde” H Cl O Br H 1 2 3 4 5 H F O 1 2 3 4 5 H H O O Cl Br 1 2 3 4 H O H 1 2 3 4 5 6 H O 1 2 3 4
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IUPACofKetones Rules: Replacethe“e”inthealkanenamewith“‐one” Thelongestchainmustcontaintheketonegroup Numberthechainchainsuchthattheketonegetsthelowestnumberpossible IUPACname: Commonname: (acceptedbyIUPAC) O O 1 2 3 O 1 2 5
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McMurry,J.OrganicChemistry,8 th Ed.,Brooks/Cole,CengageLearning,2012. O 1 2 3 4 5 6 O O 1 2 3 4 5 6 O 1 2 3 O H O 1 2 3 4 O OH O O H acetyl Formyl 1 2 3 4 5 6 6
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Preparation of Aldehydes and Ketones Preparation of Aldehydes: 4 methods 1) Oxidation 1° alcohols 2) Oxidative cleavage of alkenes (by ozonolysis) 3) Hydroboration / oxidation of terminal alkynes OH PCC CH 2 Cl 2 H H 1) O 3 2) Zn / H + C CH R 1. BH 3 / THF 2. H 2 O 2 / KOH Al H 4) Partial reduction of an ester using the reducing reagent called DIBAH ( D i i so b utyl a luminum h ydride) The reaction is normally carried out at -78 o C in Toluene, to minimize complete reduction OCH 3 O 1) DIBAH, toulene, -78 o C 2) H 3 O + 7
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