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K speciroscору апd El-mass specromетy. a) Aldol reactions require the formation of a nucleophile. Draw an electron-pushing mechanism for the formation of the enolate nucleophile in this reaction. Include all important resonance structures of the resulting nucleophile.

K speciroscору апd El-mass specromетy. a) Aldol reactions require the formation of a nucleophile. Draw an electron-pushing mechanism for the formation of the enolate nucleophile in this reaction. Include all important resonance structures of the resulting nucleophile.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.18P
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2) The Claisen-Schmidt (crossed-aldol) reaction of vanillin and acetone is carried out under basic conditions followed by acidic workup as shown below. Answer the questions associated with the procedure and use the provided spectra to analyze the products of the reaction. CH3 ÇH3 он CH3 он CH3 1) 10 % aq. NaoH 2) аq. HCI но но HO HO HO Experimental procedure To a 10 mL round bottom flask containing a stir bar was added acetone (0.784 g, 1.00 mL, 13.4 mmol), vanillin (0.198 g, 1.3 mmol), and aq. 10% sodium hydroxide solution (~3 mL). The mixture was heated at reflux for 60 min and then cooled in an ice bath. The reaction mixture was transferred to a beaker and aq. HCl solution (-30 mL, 1.2 M) added with stirring. The resulting tan precipitate was isolated by vacuum filtration, washed with ice-cold water (~2 × 5 mL), and air dried. The product was analyzed by NMR and IR spectroscopy and El-mass spectrometry. a) Aldol reactions require the formation of a nucleophile. Draw an electron-pushing mechanism for the formation of the enolate nucleophile in this reaction. Include all important resonance structures of the resulting nucleophile.
Transcribed Image Text:2) The Claisen-Schmidt (crossed-aldol) reaction of vanillin and acetone is carried out under basic conditions followed by acidic workup as shown below. Answer the questions associated with the procedure and use the provided spectra to analyze the products of the reaction. CH3 ÇH3 он CH3 он CH3 1) 10 % aq. NaoH 2) аq. HCI но но HO HO HO Experimental procedure To a 10 mL round bottom flask containing a stir bar was added acetone (0.784 g, 1.00 mL, 13.4 mmol), vanillin (0.198 g, 1.3 mmol), and aq. 10% sodium hydroxide solution (~3 mL). The mixture was heated at reflux for 60 min and then cooled in an ice bath. The reaction mixture was transferred to a beaker and aq. HCl solution (-30 mL, 1.2 M) added with stirring. The resulting tan precipitate was isolated by vacuum filtration, washed with ice-cold water (~2 × 5 mL), and air dried. The product was analyzed by NMR and IR spectroscopy and El-mass spectrometry. a) Aldol reactions require the formation of a nucleophile. Draw an electron-pushing mechanism for the formation of the enolate nucleophile in this reaction. Include all important resonance structures of the resulting nucleophile.
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