What is the appropriate sequence of reaction conditions used to synthesize valine from acetamidomalonic ester? A)(1)NaOH; (2)(CH₃)₂CHBr; (3)Cl₂,H₂O,heat B)(1)NaOCH₂CH₃; (2)(CH₃)₂CH₂CHBr; (3)HCl,H₂O,heat C)(1)NaOCH₂CH₃; (2)(CH₃)₂CHBr; (3)HCl,H₂O,heat D)(1)NaOH; (2)CH₃CH₂CH₂Br; (3)HCl,H₂O,heat

Question

Quizplus · Accepted Answer

The correct sequence of reaction conditions to synthesize valine from acetamidomalonic ester includes:
(1) Deprotonate the α-carbon adjacent to the carbonyl group using NaOCH(CH3)2, resulting in the formation of a β-ketoester.
(2) React the β-ketoester with bromoacetaldehyde diethyl acetal to give a pyridine ring system.
(3) Hydrolyze the pyridine ring using HCl to get valine product.

Option A is incorrect because it uses Cl(CH2)11SH instead of bromoacetaldehyde diethyl acetal, which will not lead to the formation of the pyridine ring required for the synthesis of valine.

Option B is incorrect because the second step uses CHCl3 instead of bromoacetaldehyde diethyl acetal, and the third step uses heat and H2SO4 instead of HCl, making this sequence unsuitable for the synthesis of valine.

Option D is incorrect because it uses a different sequence of reactants and conditions that do not lead to the synthesis of valine.

What Is the Appropriate Sequence of Reaction Conditions Used to Synthesize