1. Propose a reasonable multi-step synthesis for the following transformation. Show your work. Your final answer should be the forward series of reactions that would result in formation of the following molecule. Acetylene is your only source of carbons. You use as many acetylene molecules as you would like. H=H acetylene TSO

1. Propose a reasonable multi-step synthesis for the following transformation. Show your work. Your final answer should be the forward series of reactions that would result in formation of the following molecule. Acetylene is your only source of carbons. You use as many acetylene molecules as you would like. H=H acetylene TSO

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter16: Synthesis Workshop 1

Section: Chapter Questions

Problem 25E

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

1. Propose a reasonable multi-step synthesis for the following transformation. Show your work.
Your final answer should be the forward series of reactions that would result in formation of
the following molecule.
Acetylene is your only source of carbons. You use as many acetylene molecules as you would
like.
H=H
acetylene
TSO

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