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

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Chapter1: Chemical Foundations
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H3C-
H3C.
OH
XT
H Et
H2N–CH2CH3
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.
Arrow-pushing
Instructions
+N.
H
DCC
alb
:A
alo
H3C
H3C
CH₂CH3
Et
H-A
Transcribed Image Text:H3C- H3C. OH XT H Et H2N–CH2CH3 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. Arrow-pushing Instructions +N. H DCC alb :A alo H3C H3C CH₂CH3 Et H-A
ala
OH
H3C
EtNH,
Submit Answer
+
H3C.
:0:
H2N–CH2CH3
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.
Arrow-pushing Instructions
NOC XT
Retry Entire Group
HN
C6H11
DCC
'N
C6H11
al
H
H3C
9 more group attempts remaining
H3C
- "
CH₂CH3
Et
:0:
NH₂
HN
C6H11
N
C6H11
Transcribed Image Text:ala OH H3C EtNH, Submit Answer + H3C. :0: H2N–CH2CH3 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. Arrow-pushing Instructions NOC XT Retry Entire Group HN C6H11 DCC 'N C6H11 al H H3C 9 more group attempts remaining H3C - " CH₂CH3 Et :0: NH₂ HN C6H11 N C6H11
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