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a)
Interpretation:
The
Concept introduction:Acetoacetic ester synthesis converts an alkyl halide in to a methyl
To state:The alkyl halide which can be used to prepare 5-methyl-2-hexanone by acetoacetic ester synthesis.
b)
Interpretation:
The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis is to be stated.
concept introduction: Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.
To state: The alkyl halide which can be used to prepare 5-phenyl-2-pentanone by acetoacetic ester synthesis.
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Chapter 22 Solutions
Organic Chemistry
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardWhat is the product of the following ketone reduction reaction? Ni + H2 O cyclohexanone O cyclohexanal O cyclohexane O cyclohexanolarrow_forwardIdentify the alkyne you would use to prepare the following ketone via acid-catalyzed hydration.arrow_forward
- The following molecule belongs to a class of compounds called enediols. Each carbon of the double bond carries an —OH group: Draw structural formulas for the α-hydroxyketone and the α-hydroxyaldehyde with which this enediol is in equilibrium. α-hydroxyketone α-hydroxyaldehydearrow_forwardhow to synthesize 2-phenylclohexanone from cyclohexanone?arrow_forwardDraw out the reaction mechanism for cyclohexanol to cyclohexanone. Sodium hypochlorite oxidation of an alcohol to a ketone with the product being cyclohexanone.arrow_forward
- Draw the structures of the initially formed enol tautomers in the reactions of propyne and dicyclohexylethyne with dicyclohexylborane followed by NaOHNaOH and H2O2H2O2arrow_forwardIn each reaction box, place the best reagent and conditions from the available reagent list. 1. MCPBA 2. OH 3. 4. Answer Bank В,Н, Н, О, SOCI, H;O* O3 HBr I,, NaOH THF H,CO CH;MgBr Br, KMNO4 CH,SCH,arrow_forwardWhich of the following will readily undergo decarboxylation upon heating?arrow_forward
- When 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_forwardConsider the five compounds shown that can be generated from carbonyls. OH £ £ Ν A B 0 D E Select the compound which would NOT yield 2-propanone (or propan-2-one) when treated with H₂O, H₂O+: ○ A Select the compound which would yield 2-propanone (or propan-2-one) when treated with H₂O, OH¯: Ꭰ E B C Select the compound prepared from acetone, 1,2-ethanediol (or ethane-1,2-diol), and an acid catalyst: B A E A C B ○ Earrow_forwardplease help me draw thisarrow_forward
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