Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its 13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that product. NH3 ? 5.8 5.7 2.2 7 6 Chemical shift (ppm) 10 9. 8 4 3 2 1

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
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Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its
13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that
product.
NH3
?
5.8
5.7
2.2
7 6
Chemical shift (ppm)
10
9.
8
4
3
2
1
Transcribed Image Text:Reaction of 2,5-hexanedione with ammonia produces a compound whose 'H NMR spectrum is shown below. Its 13C NMR spectrum exhibits three signals. Draw the complete, detailed mechanism leading to the formation of that product. NH3 ? 5.8 5.7 2.2 7 6 Chemical shift (ppm) 10 9. 8 4 3 2 1
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