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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: predict the major product
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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mona840 (700)

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predict the major product      :(

 


 



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zorro (106)

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zorro (106)

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I think cyclohexane will be major but not very much sure..

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ashish_banga (927)

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i think zorro, the =O group is protected by the HS - CH2 - CH2 - HS

what raney nickel do , i dont know

i am sure about the first step



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zorro (106)

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yup! u r true...

first it will form ketal like product, then raney nickel will reduce to cyclohexane and ethanedithiol,

I think soo....but not very much sure..

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sandeepramesh (1245)

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this rn is well known and is called mosingo rn. The major product will be cyclohexane!

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tarinbansal (3304)

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I too think the major product shud be cyclohexane. Dont know abt this mosingo rn but I hav shown the intermediate formed in this reaction in the figure. Now Ni will just reduce it to give cyclohexane.


As Ni is an adsorption catalyst so a probable mechanism of reduction might be that the lone pairs of S get adsorbed on Ni catalyst and then as adsorption process continues and other molecules/species attack, this HS-CH2-CH2-SH group will leave the ring thus forming cyclohexane.



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sandeepramesh (1245)

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yes the intermediate is a thioketal as shown by tarin and then its reduced .


Note this is an alternate method for reducing aldehydes or ketones into alkanes apart from Clemmensen and Wolff Kishner. This is the better method of the three (Why?)

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isomniac (82)

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hats off to tarin


the rxn is called mozingos reduction


 

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