Exercícios - Química Orgânica 3 2020 2

QUÍMICA ORGÂNICA 3 PROF FRANCISCO AQUINO 1Desenhe as formas enol das seguintes moléculas a4metilciclohexanona bTioactetato de etila cAcetato de metila dButanal eÁcido propiónico f1fenil2butanona 2 Quantos hidrgêniosácidos cada uma das moléculas da pergunta anterior tem Classificálos 3 Indique os hidrogênios alfa nas moléculas abaixo 4 Desenhe todas as formas de monoenol para a seguinte molécula Quais são os mais estáveis Por quê Enol and Enolate Questions Qu1 How many αhydrogens are there in each of the following aldehydes and ketones a CH32CO b CH3CHO c H2CO d PhCHO e 2pentanone f 3pentanone Qu 2 For each of the following pairs of compounds draw their enols tautomers and choose the one the compound that has the greater enol content a b c Qu 3 Draw the stepwise curly arrow mechanism for the tautomerisation of propanone with i and acid catalyst H3O and ii a base catalyst HO Qu 4 What are the major products of the reactions of 1phenylethanone acetophenone with each of the following a Bromine in acetic acid acetophenone b Iodine in sodium hydroxide solution c i NaOH then ii add ethyl iodide d Ethyl magnesium bromide followed by acidic work up e NaOH and methanal f NaOH and benzaldehyde What are the major products of the reactions of 2cyclohexenone with each of the following Qu 5 a NH3 in water b Ethanethiol c Lithium diethylcuprate then acidic workup d Ethyl lithium then acidic workup 6 Write the structure of the product for the following reactions Refs httpschemlibretextsorgBookshelvesOrganicChemistryMap3AOrganicChemistryWade 233AAlphaSubstitutionsandCondensationsofCarbonylCompounds23023AEnolsandEnolateIons httpswwwchemucalgarycacourses351Carey5thCh18ch181html preparation of the enolate