(a) dl-Glutamic acid has been synthesized from diethyl acetamidomalonate in the following way. Outline the reactions involved....

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(a) dl-Glutamic acid has been synthesized from diethyl acetamidomalonate in the following way. Outline the reactions involved.

(b) Compound G has also been used to prepare the amino acid dl-ornithine through the following route. Outline the reactions involved here.

(L-Ornithine is a naturally occurring amino acid but does not occur in proteins. In one metabolic pathway l-ornithine serves as a precursor for L-arginine.)

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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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Question Posted: Apr 19, 2016 09:34 AM

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(a) dl-Glutamic acid has been synthesized from diethyl acetamidomalonate in the following way. Outline the reactions involved....

Question:

O CO Et concd HCi CN EOH (i (C12H18N20,) - → DL-glutamic acid (95% yield) (66% yield) Diethyl acetamido malonate Ha. Ni concd HC G (C12H18N20s C 1000 psi H (C10H16N2O4, a δ-lactam) reflux 4h (97% yield) DL-ornithine hydrochloride 68C, (90% yield)

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Organic Chemistry

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