As shown below, the drug novocaine can be prepared according to the retrosynthetic sequence outlined. H₂N O₂N Novocaine OH robin A O₂N B CI HO C E HN F (i) An FGI of novocaine leads to nitro-containing compound A. What does FGI stand for and what reagents might one choose to achieve this transformation in the forward sense (i.e. A to novocaine)? (ii) Disconnection of A leads to synthetic equivalents B and C. Show this disconnection, provide structures of the synthons, and explain how these relate to B and C. (iii) Provide a mechanism for the forward reaction, i.e. reaction of B with C to form A.

As shown below, the drug novocaine can be prepared according to the retrosynthetic sequence outlined. H₂N O₂N Novocaine OH robin A O₂N B CI HO C E HN F (i) An FGI of novocaine leads to nitro-containing compound A. What does FGI stand for and what reagents might one choose to achieve this transformation in the forward sense (i.e. A to novocaine)? (ii) Disconnection of A leads to synthetic equivalents B and C. Show this disconnection, provide structures of the synthons, and explain how these relate to B and C. (iii) Provide a mechanism for the forward reaction, i.e. reaction of B with C to form A.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

As shown below, the drug novocaine can be prepared according to the retrosynthetic sequence
outlined.
or
H₂N
O₂N
Novocaine
OH
robin
↓↓
O₂N
B
CI
HO
E
HN
F
(i)
An FGI of novocaine leads to nitro-containing compound A. What does FGI stand for and what
reagents might one choose to achieve this transformation in the forward sense (i.e. A to
novocaine)?
(ii) Disconnection of A leads to synthetic equivalents B and C. Show this disconnection, provide
structures of the synthons, and explain how these relate to B and C.
(iii) Provide a mechanism for the forward reaction, i.e. reaction of B with C to form A.
(iv) Compound B can be prepared from carboxylic acid D. What reagent would you select in order
to convert D into B?
(v) Amino alcohol C can be prepared from epoxide E and amine F. Accordingly, show the
retrosynthesis of C and then a mechanism for the forward reaction.

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