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April 26, 2015

Homework Help: organic chem

Posted by adam on Tuesday, April 26, 2011 at 5:13am.

(b) One of your illustrious colleagues continues his/her education and finally obtains employment with a renowned pharmaceutical company as an organic chemist. He or she is asked to synthesize pantothenic acid because the company wants to use it to prepare a synthetic form of coenenzyme A. Your colleague devises a seven-step synthesis for pantothenic acid:

(1) Isobutyraldehye + formaldehyde + NaOH/H2O → II (C5H10O2)
(2) II + NaCN → (C6H10O2 NNa) + H2O → III (C6H11O2 N) + NaOH
(3) III + H2O + H2SO4 + heat → IV (C6H12O4) + NH4HSO4
(4) IV + H3O+ + heat → V (C6H10O3)
(5) V + NaOH + heat → VI (C6H11O4Na)
(6) VI + sodium 2-aminopropionate → sodium pantothenoate + H2O
(7) Sodium pantothenoate + HCl(aq) → pantothenic acid + NaCl(aq)

(a) Suggest structures for II, III, IV, V, and VI.





(b) Give a brief rationale for the non-basic activity of the nitrogen in pantothenic acid.



(c) Write chemical equations to explain the reactions of pantothenic acid with NaOH, ethyl alcohol, and hot NaOH as described in (a), (b), and (c) above.

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