(a) Illustrate the Strecker synthesis of phenylalanine. Is the product chiral? Does it exhibit optical activity? (b)...

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(a) Illustrate the Strecker synthesis of phenylalanine. Is the product chiral? Does it exhibit optical activity? 

(b) It has been found that replacement of NH3 by an optically active amine in the Strecker synthesis of phenylalanine leads to an excess of one enantiomer of the product. Assign the R or S confi guration to each stereocenter in the following structures, and explain why the use of a chiral amine causes preferential formation of one stereoisomer of the final product. 

NH2 HCN H;C H CH2 H C-N TH H,C 1. H*, H,O 2. Н, Ра- С CH,CH -CH2 Hc-NH3 -H,0 c–NH3 H NC CO0 Mainly Mainly

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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