H3C-H3C.OHXTH EtH2N–CH2CH3It is difficult to prepare an amide from a carboxylic acid and an amine directly, since an acid-base reaction occurs which renders theamine nitrogen non-nucleophilic. Typically, in such an amide synthesis, the carboxylic acid OH group is first transformed into a better,nonacidic leaving group. In practice, amides are often prepared by treating the carboxylic acid with dicyclohexylcarbodiimide (DCC).The amine is then added and nucleophilic acyl substitution occurs easily because dicyclohexylurea is a good leaving group. Thismethod of amide bond formation is a key step in the laboratory synthesis of peptide bonds (amide bonds) between protected aminoacids.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushingInstructions+N.HDCCalb:AaloH3CH3CCH₂CH3EtH-A alaOHH3CEtNH,Submit Answer+H3C.:0:H2N–CH2CH3It is difficult to prepare an amide from a carboxylic acid and an amine directly, since an acid-base reaction occurs which renders theamine nitrogen non-nucleophilic. Typically, in such an amide synthesis, the carboxylic acid OH group is first transformed into a better,nonacidic leaving group. In practice, amides are often prepared by treating the carboxylic acid with dicyclohexylcarbodiimide (DCC).The amine is then added and nucleophilic acyl substitution occurs easily because dicyclohexylurea is a good leaving group. Thismethod of amide bond formation is a key step in the laboratory synthesis of peptide bonds (amide bonds) between protected aminoacids.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsNOC XTRetry Entire GroupHNC6H11DCC'NC6H11alHH3C9 more group attempts remainingH3C- "CH₂CH3Et:0:NH₂HNC6H11NC6H11

DCC reacts with carboxylic acid group to produce a better leaving group. Amine attacks on the…

H3C- OH Arrow-pushing Instructions H3C. ANC↔XT It is difficult to prepare an amide from a carboxylic acid and an amine directly, since an acid-base reaction occurs which renders the amine nitrogen non-nucleophilic. Typically, in such an amide synthesis, the carboxylic acid OH group is first transformed into a better, nonacidic leaving group. In practice, amides are often prepared by treating the carboxylic acid with dicyclohexylcarbodiimide (DCC). The amine is then added and nucleophilic acyl substitution occurs easily because dicyclohexylurea is a good leaving group. This method of amide bond formation is a key step in the laboratory synthesis of peptide bonds (amide bonds) between protected amino acids. Draw curved arrows to show the movement of electrons in this step of the mechanism. H Et H H2N—CH2CH3 :A DCC H3C пояда H3C- CH₂CH3 Et H-A

H3C- OH Arrow-pushing Instructions H3C. ANC↔XT It is difficult to prepare an amide from a carboxylic acid and an amine directly, since an acid-base reaction occurs which renders the amine nitrogen non-nucleophilic. Typically, in such an amide synthesis, the carboxylic acid OH group is first transformed into a better, nonacidic leaving group. In practice, amides are often prepared by treating the carboxylic acid with dicyclohexylcarbodiimide (DCC). The amine is then added and nucleophilic acyl substitution occurs easily because dicyclohexylurea is a good leaving group. This method of amide bond formation is a key step in the laboratory synthesis of peptide bonds (amide bonds) between protected amino acids. Draw curved arrows to show the movement of electrons in this step of the mechanism. H Et H H2N—CH2CH3 :A DCC H3C пояда H3C- CH₂CH3 Et H-A

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter18: Carboxylic Acids

Section: Chapter Questions

Problem 18.54P

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