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Ask iit jee aieee pet cbse icse state board experts Expert Question: Organic Conversion - Pls help Urgent
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[Post New]9 Apr 2008 21:51:04 IST
    Subject: Organic Conversion - Pls help Urgent
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priyesh (1586)

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suggest a suitable method for the following conversion
 
see the image below
 

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[Post New]9 Apr 2008 21:53:24 IST
    Subject: Organic Conversion - Pls help Urgent
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akhil_o (2704)

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edit sorry...
i reversed the reaction
:O
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[Post New]9 Apr 2008 21:53:52 IST
    Subject: Organic Conversion - Pls help Urgent
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sunip_the_mini_mastermind (133)

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first react it with 2 moles of any alcohol ...then reduce the comp with sodium borohydride..and then do acidic hydrolysis.....the func of alcohol is that it will protect the aldehyde from being reduced
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[Post New]9 Apr 2008 21:57:13 IST
    Subject: Organic Conversion - Pls help Urgent
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priyesh (1586)

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@akhil PCC oxidises here we want reduction
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[Post New]9 Apr 2008 21:57:49 IST
    Subject: Organic Conversion - Pls help Urgent
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priyesh (1586)

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@sunip canu give me a mechanism of the reaction pls..
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[Post New]9 Apr 2008 22:05:47 IST
    Subject: Re:Organic Conversion - Pls help Urgent
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arpan1 (665)

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i hope LiAlH4 will do the needful


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all the best ...
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[Post New]9 Apr 2008 22:09:36 IST
    Subject: Organic Conversion - Pls help Urgent
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kundan_leo (1183)

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yup lialh4 will do the job.............
will reuce the ketone first to corresponding alcohol........

excess of it will reduce aldehyde ....as well
" the only thing thats always constant in this world , is change itself.....
so it is better to adapt to the situation or life makes you adapt to it (painfully)..."
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[Post New]9 Apr 2008 22:11:59 IST
    Subject: Organic Conversion - Pls help Urgent
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ananth_patri (585)

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no LiAlh4 reduces both the groups CHO and =O so u ll have to protect the CHO group..
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[Post New]9 Apr 2008 22:17:01 IST
    Subject: Re:Organic Conversion - Pls help Urgent
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arpan1 (665)

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ya , i think ananth is right

lemme think then

will post soon
all the best ...
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[Post New]9 Apr 2008 22:39:19 IST
    Subject: Re:Organic Conversion - Pls help Urgent
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ramkumar_november (1266)

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first  do schmidt reaction that will convert CHO to CN....it will not affect the ketone.....
 
then use meerwein-pondorf-verley reduction..... that will reduce C=O  to CH--OH........ it will not affect the CN group........
 
then hydrolyse and convert CN to COOH..... then convert to COCl.... then do rosenmund reduction to get back the aldehyde group........
 
reagents for the reactions are.....
 
schmidt reaction-->hydrazoic acid(HN3)+conc H2SO4
 
meerwein pondorf verley reduction---->aluminium iso propoxide
 
rosenmund reduction----->H2/palldium/BaSO4/quinoline
 
please tell me if there is any error in my steps......
 
 
 
 
 
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[Post New]10 Apr 2008 14:41:49 IST
    Subject: Organic Conversion - Pls help Urgent
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varshavallig (798)

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first oxidise the CHO grp to COOH with PCC.C=O will not b affected.
now reduce C=O grp using H2/Pd to CHOH.COOH will be unreactive to H2/Pd.convert COOH to COCl and do rosunmund's reduction to get back CHO grp.
plz tell me if there is anything wrong in this method
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[Post New]10 Apr 2008 15:24:32 IST
    Subject: Re:Organic Conversion - Pls help Urgent
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layman (148)

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Protect the aldehyde using glycol(converted into acetal).
Then reduce using LiAlH4 and finally hydrolyse to get the product.


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[Post New]10 Apr 2008 16:38:10 IST
    Subject: Re:Organic Conversion - Pls help Urgent
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karthik2789 (57)

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protect the aldehyde by glycerol( diol), reduce the keto by nabh4, hydrolyse it to the protected gp.
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[Post New]10 Apr 2008 17:15:01 IST
    Subject: Organic Conversion - Pls help Urgent
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ramkumar_november (1266)

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varshavallig's method is correct.......

layman and karthik2789 ...... when you try to protect the aldehyde group using glycerol....... even ketone is protected.....
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[Post New]10 Apr 2008 18:33:44 IST
    Subject: Organic Conversion - Pls help Urgent
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karthik2007 (3351)