[Vidya]

I am having difficulties figuring out how to convert cyclohexanone into CYCLOHEXANECARBOXYLIC ACID; does anybody have an idea?

Thank you very much in advance!

Use HCN and hydrolyze with H3O+ and heat it.CN will be converted to COOH and OH will be eliminated out as H2O ....now reduce the double bond formed due to elimination of water with Pl/H2 ..it will not effect your COOH 

[Maud]

I am having difficulties figuring out how to convert cyclohexanone into CYCLOHEXANECARBOXYLIC ACID; does anybody have an idea?

Thank you very much in advance!

Use HCN and hydrolyze with H3O+ and heat it.CN will be converted to COOH and OH will be eliminated out as H2O ....now reduce the double bond formed due to elimination of water with Pl/H2 ..it will not effect your COOH

Thanks a lot but... why would the hydrolisis of the CN be accompanied by the elimination of the -OH? It does not usually happen in the cyanohydrin acid-catalyzed hydrolysis. Indeed, it leads to the α-hydroxycarboxylic acid....

[Maud]

Mmm, I am really not sure about it... I would think about a condensation but... what about the ketone? Maybe I should do a reduction first....

There are many routes that a compound can be made and class assignments usually use them. However, we were not in the class to know. The acid could be synthesized via a condensation reaction, but not very easily. This question is frequently used with Grignard reactions. We could tell you exactly how it can be done and if you told us which textbook you were using, the page it could be found on. This will not help you on a test though.

Hint, if you had an alcohol, how could you make a bromide?

@kriggy
Re: retrosynthesis
I am old school. We learned how to do this before the term became popular. Now, this is my opinion about this. Students are virtually unable to think about possible reverse reactions unless they have first mastered the forward reactions.

The posters proposed Grignard could actually be a plausible step if applying retrosynthesis in a strict manner. It fails due to the implausible nature of the reagent. To that end, I virtually abandoned asking for starting materials until or unless I could no longer create a useful problem, e.g. Diels-Alder reactions. Think about it, does this post really show the poster is unaware of retrosynthesis or the reactions to complete it?

I would react the ROH with HBr.

I agree... retrosynthesis is extremely difficult for me... (thanks for understanding)