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Organic Chemistry

Cool goIITian

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21 Oct 2008 07:21:44 IST

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497

Nucleophilic Substituition

None

Which would be allow lesser racemization if it is assumed only SN 1 reaction takes place ?

a) CH3-S-CH(CH3)-Br (in Ethoxide solution)

b) CH3-CH2-CH(CH3)-I (in presence of hydroxide ion)

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Madhusudan Chavan

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Joined: 9 Mar 2007

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21 Oct 2008 20:10:33 IST

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As the reaction is assumed to be SN1 only means that carbocation is formed, hence it would depend on the stability of the carbocation. In the first compound (a) the carbocation can be stabilized ,apart from the hyperconjugation of methyl group,by the resonance- the lone pair of electrons on sulphur can enter into resonance with the carbocation.( CH3-S(+)=CH-CH3). In second no such structure is possible, the carbocation is stabilised by hyperconjugation only. Hence more racemisation is possible in the first one.

Tuhin Sarkar

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Joined: 11 Jun 2008

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4 Nov 2008 11:25:46 IST

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Sir , Actually the question was miswritten.

It was to compare racemization between--- CH3-CH2-S-CH2-Br and CH3CH2-CH(CH3)-I all other conditions remaining same.

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