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Why is 1-bromotriptycene inert to nucleophilic substitution?
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Mike Webster
Why is 1-bromotriptycene inert to nucleophilic substitution?
Sn1 reaction proceed through carbocation intermediate which has planar structure. The structure of 1-bromo triptycene is cage like structure so the bridgehead carbon cannot assume planarity , hence,the formation of a carbocation at the bridgehead position does not take place. Consequently 1-bromotriptycene is inert to sn1reaction.
Sn1 reaction proceed through carbocation intermediate which has planar structure. The structure of 1-bromo triptycene is cage like structure so the bridgehead carbon cannot assume planarity , hence,the formation of a carbocation at the bridgehead position does not take place. Consequently 1-bromotriptycene is inert to sn1reaction.
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Bredt's rule is a consequence of the fact that having a double bond on a bridgehead or carbocation is not stable for small rings (fewer than eight atoms) due to a combination of ring strain, and angle strain (nonplanar alkene).Since SN1 reaction involves carbocation intermediate, and such intermediate is not possible here, hence SN1 IS RULED OUT.SN2, reaction involves a backside attack from the leaving group.Due to stearic hinderence to the backside attack, such a reaction is also not possible.Totally nucleophilic substitution is not possible.
Bredt's rule is a consequence of the fact that having a double bond on a bridgehead or carbocation is not stable for small rings (fewer than eight atoms) due to a combination of ring strain, and angle strain (nonplanar alkene).Since SN1 reaction involves carbocation intermediate, and such intermediate is not possible here, hence SN1 IS RULED OUT.SN2, reaction involves a backside attack from the leaving group.Due to stearic hinderence to the backside attack, such a reaction is also not possible.Totally nucleophilic substitution is not possible.
Sn1 reaction proceed through carbocation intermediate which has planar structure. The structure of 1-bromo triptycene is cage like structure so the bridgehead carbon cannot assume planarity , hence,the formation of a carbocation at the bridgehead position does not take place. Consequently 1-bromotriptycene is inert to sn1reaction.
Sn1 reaction proceed through carbocation intermediate which has planar structure. The structure of 1-bromo triptycene is cage like structure so the bridgehead carbon cannot assume planarity , hence,the formation of a carbocation at the bridgehead position does not take place. Consequently 1-bromotriptycene is inert to sn1reaction.
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Bredt's rule is a consequence of the fact that having a double bond on a bridgehead or carbocation is not stable for small rings (fewer than eight atoms) due to a combination of ring strain, and angle strain (nonplanar alkene).Since SN1 reaction involves carbocation intermediate, and such intermediate is not possible here, hence SN1 IS RULED OUT.SN2, reaction involves a backside attack from the leaving group.Due to stearic hinderence to the backside attack, such a reaction is also not possible.Totally nucleophilic substitution is not possible.
Bredt's rule is a consequence of the fact that having a double bond on a bridgehead or carbocation is not stable for small rings (fewer than eight atoms) due to a combination of ring strain, and angle strain (nonplanar alkene).Since SN1 reaction involves carbocation intermediate, and such intermediate is not possible here, hence SN1 IS RULED OUT.SN2, reaction involves a backside attack from the leaving group.Due to stearic hinderence to the backside attack, such a reaction is also not possible.Totally nucleophilic substitution is not possible.
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