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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: QUESTION OF THE DAY
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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[Post New]11 Mar 2008 17:22:42 IST
    Subject: QUESTION OF THE DAY
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dev_22oct (1326)

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Explain the following facts
 
treating (z)-2-butene with OsO4 in pyridine and then NaHSO3 in water gives a diol that is inactive and cannot be resolved.
 
 
 
 
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[Post New]11 Mar 2008 18:03:30 IST
    Subject: Re:QUESTION OF THE DAY
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hash_include (381)

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i think this is a syn addition of alkenes.
it gives meso 2,3 butan-di-ol, hence its inactive and can't be resolved
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[Post New]11 Mar 2008 19:50:38 IST
    Subject: QUESTION OF THE DAY
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tarinbansal (2432)

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Hydroxylation of alkenes with OsO4 is a syn hydroxylation and primarily leads to the formation of a meso compound and hence the product is optically inactive and cant be resolved.
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[Post New]11 Mar 2008 21:26:07 IST
    Subject: QUESTION OF THE DAY
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neeraj_agarwal_1990 (909)

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yup
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[Post New]11 Mar 2008 22:13:18 IST
    Subject: Re:QUESTION OF THE DAY
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dev_22oct (1326)

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good!!
 
syn hydroxylation at either face of (Z) -alkene leads to the meso compound
(2R,3S)-2,3-butanediol.
 
 
                 z-2.butene(syn-hydroxylation)-------->2,3- butanediol
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