Question

nic natural compo ison in tribal war Dal transition states involved in formation or 5 sequence of reactions from the early steps in a synthesis of fluorooleic acid, a toxie Fluorooleic acid, also called "rarsbane," has been used to kill rats and also as an arrow poison in are required to complete its synthesis.) octane + sodium acetylide (the sodium salt of ethyne) compound A (C10H, F) 2. Consider the following sequence of reas from an African shrub. (e-Fluorooleic acid, al wo more steps beyond those below are required to compe (i) 1-Bromo-8-fluorooctane + sodium acetylic Compound A + NaNH- compound B (C10H16FNa) (iii) Compound B +1-(CH2)7-C1- compound C (C17! (iv) Compound C + NaCN- compound D (C18H30NF) (a) Elucidate the structures of compounds A, B, C, and D above. (b) Write the mechanism for each of the reactions above. (c) Write the structure of the transition state for each reaction.

Answer 1

Ques-2 (1) I-Boomo - 8 - fluomodrane + Bodlumawryeide + Na-E-H J 5Na Mechanism Hi F-CH ₂ - (CH2)2 -C- 8-7 Be Transition Star compound (8) 2-H (clo H17 F) NaNHQ IN2 I ((12)7-ce compound (©). -- (CH2)7-4 SNA NaCN

compound (D) - (42)6-CH2-CENI L3-49) Shuurwel of Transis Hom stave (c) g. I g- F-Hg - (CH) - --------I El-147 - (Halia H Shruture of Transistion State of compound (D) NC--- ----ll (F-46-(4-3-3)