The positive charge in dragmacidin D is delocalized. Draw all resonance structures that show delocalization of this charge, by modifying the given structures as needed. Include the original structure as one of the possible resonance forms, and include relevant formal charges in your structures. Do not add any resonance arrows or curved arrows. Use the+and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds. N-H H

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section18.8: Interconversion Of Functional Derivatives
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The dragmacidin class of natural products has been isolated from various marine sponges. They have been shown to have many
interesting biological properties, including anti-viral, anti-fungal, and anti-bacterial activity. (+)- Dragmacidin D, shown below, was also
made in the laboratory, which allowed the structure to be confirmed (Org. Lett. 2015, 17, 1529-1532).
Part 1
ΗΘΗ
H-N N-H
* (-6)
R
(+)-Dragmacidin D
R =
"N-H
The positive charge in dragmacidin D is delocalized. Draw all resonance structures that show delocalization of this charge, by
modifying the given structures as needed. Include the original structure as one of the possible resonance forms, and include
relevant formal charges in your structures. Do not add any resonance arrows or curved arrows. Use the + and - tools to
add/remove charges to an atom, and use the single bond tool to add/remove double bonds.
Br
-H
Transcribed Image Text:The dragmacidin class of natural products has been isolated from various marine sponges. They have been shown to have many interesting biological properties, including anti-viral, anti-fungal, and anti-bacterial activity. (+)- Dragmacidin D, shown below, was also made in the laboratory, which allowed the structure to be confirmed (Org. Lett. 2015, 17, 1529-1532). Part 1 ΗΘΗ H-N N-H * (-6) R (+)-Dragmacidin D R = "N-H The positive charge in dragmacidin D is delocalized. Draw all resonance structures that show delocalization of this charge, by modifying the given structures as needed. Include the original structure as one of the possible resonance forms, and include relevant formal charges in your structures. Do not add any resonance arrows or curved arrows. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds. Br -H
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