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Chapter 7, Problem 54P

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QUESTION:

Problem 54P

Show how the following compounds could be synthesized starting with ethyne:

a. Cis-2-octene                  b. trans-3-heptene

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QUESTION:

Problem 54P

Show how the following compounds could be synthesized starting with ethyne:

a. Cis-2-octene                  b. trans-3-heptene

ANSWER:

Solution 54P:

Here, we are going to write the synthesizing steps to prepare the following product by using the appropriate reagents.

Step 1:

a. Cis-2-octene  

Here, acetylene reacts with amide to form acetylide ion which on react with corresponding methyl bromide to form 1-propyne. Secondly, in similar way, 1-propyne reacts with amide to form acetylide ion which react with alkyl halide to form 2-octyne. Finally, 2-octyne undergo hydrogenation reaction in presence of Lindlar’s catalyst to form the cis-2-octene as a product.

The reaction steps are given below:

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