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Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

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Published by Kunjal
O. CHEM
O. CHEM

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Published by: Kunjal on Oct 13, 2009
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12/03/2012

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CHAPTER 7
Further Reactions of Haloalkanes:Unimolecular Substitution andPathways of Elimination
 
Solvolysis of Tertiary and Secondary Haloalkanes7-1
The rate of S
N
2 reactions decrease dramatically as the reaction centerchanges from primary to secondary to tertiary.This is true only for bimolecular substitution.Secondary and tertiary halides can be substituted, however, themechanism is different.Consider the reaction of 2-bromo-2-methylpropane and water.When a substrate undergoes substitution by the solvent, the process iscalledsolvolysis. If the solvent is water, the process ishydrolysis. Water is the nucleophile, even though its nucleophilic capacity is low.
 
2-Bromopropane undergoes a similar reaction, but more slowly.
1-Bromopropane, bromoethane, and bromomethane do not reactwell under these conditions.Solvolysis also occurs in alcohol solvents:

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