ORGANIC CHEMISTRY 1 (ORC601S)
Assignment 2
Due: 11 April 2025
1. Draw a stepwise mechanism for the following reaction?
2. ω-fluoro fatty acids are metabolized in the body to produce monofluoroacetic acid, which is
known to be so poisonous and a cause of many known cases of animal food poisoning. Draw
the major product and propose a stepwise mechanism, for when ω-Fluorooleic acid is treated
with each reagent:
(a) NaOCH2CH3; (b) KCN; (c) DBU.
3. Propose a structure for an alkyl halide that gives only (E)-3-methyl-2 phenyl-2-pentene on E2
elimination. Make sure you indicate the stereochemistry.
4. Even though SN2 reactions occurs withe the inversion of stereochemistry at a stereogenic
center, the nitrile product of the reaction below also has S stereochemistry. Draw the structure
of the product and explain this observation.
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