Bridged Cyclic Compounds and SN2 Reactions
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Bridged cyclic compounds like the ones shown in the attached .jpg are extremely unreactive in SN2 reactions.
1) Give a reason which will explain this.
2) How can you explain the fact that compounds of this type are also less reactive in the SN1 reaction than similar noncyclic compounds?
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1) The SN2 reaction is a type of nucleophilic substitution, where a nucleophile attacks an electrophilic center and bonds to it, expelling another group on the OPPOSITE SIDE OF THE PRIMARY CARBON.
As you can see the nucleophile (X) attack occurs if the backside route of attack is not sterically hindered by substituents on the substrate. Therefore this mechanism usually occurs at an unhindered ...
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