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Topic: Synthesis of hexan-3-one from ethyne  (Read 4094 times)

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Offline Undergrad1591

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Synthesis of hexan-3-one from ethyne
« on: April 25, 2012, 12:31:02 AM »
Using the starting material(s) on the left as the only source(s) of
carbons in the final product and any other organic or inorganic reagents, show how to synthesize the molecule on the right. You must show all molecules synthesized along the way and the reagents needed for each step. Do not show mechanisms. You may use abbreviations found in the book or class notes, for example, t-BuOK. READ THESE INSTRUCTIONS AGAIN and be sure you understand them.

ethyne :rarrow:hexan-3-one
(all carbons must come from the ethyne; it can be used more than once)

Offline Undergrad1591

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Re: Synthesis of hexan-3-one from ethyne
« Reply #1 on: April 25, 2012, 12:42:56 AM »
I was sick when we learned this so my idea of the reaction is pretty rough, but I think it has to go through a basic tautomerization, possibly with BH3 NaOH and H2O2. I am just unsure of the other processes in this reaction.

Offline orgopete

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Re: Synthesis of hexan-3-one from ethyne
« Reply #2 on: April 25, 2012, 12:58:59 AM »
Let's see, make 3-hexanone from acetylene. Acetylene has two carbons. How can you add four carbons (2 x 2) to acetylene? (Most students only know a single carbon-carbon bond forming reaction from an acetylene. I suggest you use this reaction.)

If you need to, how could you add 2 x 2 carbons to acetylene. We'll go from there.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

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