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Chapter 29: Q44P (page 1193)

Glutamic acid is synthesized by the following reaction sequence. Draw a stepwise mechanism for Steps [1]–[3].

Short Answer

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Glutamic acid belongs to the amino acid family which is a non-essential amino acid consisting of amino and carboxylic group.It helps in cellular metabolism, improves heartbeat, remove toxic substances.

Step by step solution

01

Glutamic acid

Glutamic acid belongs to the amino acid family which is a non-essential amino acid consisting of amino and carboxylic group.It helps in cellular metabolism, improves heartbeat, remove toxic substances.

02

Mechanism of glutamic acid

In the first step, diethyl acetamidomalonate is treated with Sodium ethoxide, and it forms a compound with the removal of ethanol. In step 2, ethyl acrylate attacks the negatively charged carbon atom and forms a compound as shown below.

Then nucleophile attack to the compound an intermediate is formed in step 3.Finally, it undergoes hydrolysis to form glutamic acid.

Formation of glutamic acid

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Most popular questions from this chapter

Draw the organic products formed in each reaction

Draw the organic products formed in each reaction.

a.

b.

Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1° amines (Section 25.7A).

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Devise a synthesis of threonine from diethyl acetamidomalonate.
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