Is there any reaction available to convert cyclic compounds to their corresponding aliphatic compounds? eg. Converting cyclohexane to n hexane

  • $\begingroup$ One way I can think of is converting a cyclic compound to a ketone using wacker process, then cleaving the ketone with conc. $\ce{HNO3}$ and reducing the aldehyde obtained using clemmensen or Wolff kishner reduction. Not a straightforward way but just my two cents. $\endgroup$ Dec 28 '19 at 7:58
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    $\begingroup$ Nothing straighforward, you're looking at multiple steps some with poor yields $\endgroup$
    – Waylander
    Dec 28 '19 at 8:34
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    $\begingroup$ This question have been asked and have been answered click on the link to view the answer: chemistry.stackexchange.com/questions/15170/… $\endgroup$ Dec 28 '19 at 20:33

The reaction you want to know about is "Cleavage reaction" in particular oxidative cleavage.KMnO4 reaction in which it forms glycols and then cleaves.

In this dihydroxylation, if the solution is warm or acidic or too concentrated, oxidative cleavage of the glycol may occur.

Then they can be reduced to aldehydes by reducing agents.Reduction of carboxylic acids to aldehydes is difficult because aldehydes are more reactive than carboxylic acids toward most reducing agents. Almost any reagent that reduces acids to aldehydes also reduces aldehydes to primary alcohols.

Lithium tri-tert-butoxyaluminum hydride, LiAlH(O-t-Bu)3 is a weaker reducing agent than lithium aluminum hydride. It reduces acid chlorides to aldehydes because acid chlorides are strongly activated toward nucleophilic addition of a hydride ion.

Under these conditions, the aldehyde reduces more slowly and can be isolated. Therefore, reduction of an acid to an aldehyde is a two-step process: Convert the acid to the acid chloride, then reduce using lithium tri-tert-butoxyaluminum hydride.

Acid Chloride

Aldehyde is formed

And now we can reduce it by the Wolff Kishner reduction. Alkanes are finally formed.

Ethylene glycol, diethylene glycol, or another high-boiling solvent is used to facilitate the high temperature (140–200 °C) needed in the second step. I am assuming you can convert the cyclohexane to cyclohexene by any radical halogenation and then dehydrohalogenation.

  • $\begingroup$ How do I add citations or references? $\endgroup$ Dec 28 '19 at 8:20
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    $\begingroup$ For the published work such as a textbook we prefer to use ACS style. I could assist you by editing the citation in your post; which textbook you've used? Looks like Wade's Organic chemistry, however, knowing the edition would be nice. Also, I'm not an organic chemist, but this doesn't seem to answer the question IMO (or at least only the last sentence addresses it). $\endgroup$
    – andselisk
    Dec 28 '19 at 8:26

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