The following reaction was attempted during the total synthesis of crispine A, a cytotoxic alkaloid isolated from a Mongolian thistle (J.Org. Chem. 2011, 76, 1605-1613). Propose a plausible mechanism for the formation of compound 2 from amine 1.H.CO.CO₂CH3[H,O*]H.CONH₂H.COH.CO2CO₂CH3 Add ONE remaining curved arrow to draw the next step of the mechanism. Modify the given drawing of the product as needed toshow the intermediate that is formed in this step (a sigma complex). Use the +/- tools to add/remove charges, and use the singlebond tool to interconvert between double and single bonds.H₂CH₂C.NH*H₂CH₂CNHEdit DrawingCH3CH3

The required answer is given belowExplanation:Step 1:Step 2: Step 3: Step 4:

Answered: The following reaction was attempted…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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When certain aromatic compounds are treated with formaldehyde (CH2O), and HCl, the CH2Cl group is introduced onto the ring. This reaction is known as chloromethylation. (a) Propose a mechanism for this example of chloromethylation. (b) The product of this chloromethylation can be converted to piperonal, which is used in perfumery and in artificial cherry and vanilla flavors. How might the CH2Cl group of the chloromethylation product be converted to a CHO group?
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?

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