522 - Practice Problem 5‐22 – Answer Propose syntheses...

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Unformatted text preview: Practice Problem 5‐22 – Answer Propose syntheses of the following derivatives of diethyl malonate, each of which is a starting material for synthesis of a barbituate. (a) (b) Practice Problem 5‐23 – Answer 2‐Propylpentanoic acid (valproic acid) is an effective drug for treatment of several types of epilepsy, particularly absence seizures, which are generalized epileptic seizures characterized by brief and abrupt loss of consciousness. Propose a synthesis of valproic acid starting with diethyl malonate. Retrosynthetic analysis: Synthesis: Practice Problem 5‐24 – Answer Propose a mechanism for formation of 2‐carethoxy‐4‐butanolactone and then 4‐butanolactone (g‐buryrolactone) in the following sequence of reactions. Practice Problem 5‐25 – Answer Show how to synthesize the following compounds using either the malonic ester synthesis or the acetoacetic ester synthesis. (a) 4‐Phenyl‐2‐butanone Retrosynthetic analysis: Synthesis: (b) 3‐Ethyl‐2‐pentanone Retrosynthetic analysis: Synthesis: (c) 4‐Oxopentanoic acid Retrosynthetic analysis: Synthesis: (d) Cyclopropanecarboxylic acid Retrosynthetic analysis: Synthesis: (e) 2‐Methylhexanoic acid Retrosynthetic analysis: Synthesis: (f) 2‐Propyl‐1,3‐propanediol Retrosynthetic analysis: Synthesis: (g) 3‐Benzyl‐5‐hexen‐2‐one Retrosynthetic analysis: Synthesis: (h) Cyclobutyl methyl ketone Retrosynthetic analysis: Synthesis: Practice Problem 5‐26 – Answer In each part below, propose a sequence of reactions to prepare the indicated target compound from the indicated starting material. You may also use any other organic and/or inorganic reagents necessary. (a) (b) ...
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas at Austin.

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