Answered: P13.4: Draw a reasonable mechanism for…

P13.4: Draw a reasonable mechanism for this decarboxylation step in tryptophan biosynthesis (EC 4.1.1.45). Hint: a tautomeriza decarboxylation. NH3 NH3

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter16: Synthesis Workshop 1

Section: Chapter Questions

Problem 3CTQ

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

P13.4: Draw a reasonable mechanism for this decarboxylation step in tryptophan biosynthesis (EC 4.1.1.45). Hint: a tautomerization step precedes the
decarboxylation.
NH3
NH3
CO,

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