Determine if the following transformation can be carried out via the formation of the corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out, explain why and propose a synthetic route that allows obtaining the product in high yield. OCH3 OH

Determine if the following transformation can be carried out via the formation of the corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out, explain why and propose a synthetic route that allows obtaining the product in high yield. OCH3 OH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter9: Alkynes: An Introduction To Organic Synthesis

Section9.SE: Something Extra

Problem 21MP

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Determine if the following transformation can be carried out via the formation of the
corresponding tosylate followed by an SN2 attack by methoxide. If it cannot be carried out,
explain why and propose a synthetic route that allows obtaining the product in high yield.
OH
OCH 3
to doon

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