Why do tosylates conversions only happen as bimolecular reactions?

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Start date Nov 13, 2012
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In summary, tosylates conversions only happen as bimolecular reactions because they require two molecules to come together in order for the reaction to occur. This is due to the formation of a stable intermediate that cannot be formed in a unimolecular reaction. Additionally, the presence of a strong leaving group on the tosylate group makes it more likely to participate in a bimolecular reaction. This mechanism allows for efficient and reliable conversions of tosylates into various functional groups.

Nov 13, 2012

member 392791

When an ROH is converted to an R--OTs, why must this mechanism be either Sn2 or E2?

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Nov 13, 2012

chemisttree

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Can you think of a mechanism where E1 or Sn1 could happen?

Nov 14, 2012

member 392791

That is circular reasoning...

My textbook doesn't present an argument for why it cannot be Sn1 or E1..which forces me just to memorize this rather than understand. Even if it was a tertiary tosylate it would still do an Sn2 reaction??

FAQ: Why do tosylates conversions only happen as bimolecular reactions?

Why are tosylate conversions limited to bimolecular reactions?

Tosylates, also known as tosyl groups, are electron-withdrawing groups that are commonly used in organic chemistry reactions. They have a strong affinity for nucleophiles, making them excellent leaving groups. However, their conversion only occurs as bimolecular reactions because they require the presence of both a nucleophile and an electrophile to undergo substitution. This is due to the way tosylates are activated, as they require simultaneous interaction with both a nucleophile and an electrophile to undergo substitution.

What makes tosylates different from other leaving groups?

Tosylates are unique leaving groups because of their strong electron-withdrawing ability and their ability to stabilize negative charges. This makes them excellent leaving groups in substitution reactions. Additionally, tosylates are relatively easy to prepare and handle, making them commonly used in organic synthesis.

How do tosylate conversions compare to other substitution reactions?

Tosylate conversions are typically faster and more efficient compared to other substitution reactions, such as SN1 or SN2 reactions. This is because tosylates have a lower activation energy, making them more reactive and favorable in substitution reactions. Additionally, tosylate conversions have a higher yield and fewer side products compared to other substitution reactions.

Can tosylates undergo other types of reactions?

Yes, tosylates can undergo a variety of reactions, including elimination, reduction, and nucleophilic addition reactions. These reactions occur through different mechanisms and are dependent on the reaction conditions and the nature of the tosylate compound. However, tosylate conversions are the most common and well-studied reactions involving tosylates.

Are there any limitations to using tosylates in organic synthesis?

While tosylate conversions are generally efficient and reliable, there are some limitations to their use in organic synthesis. One limitation is that tosylates can only be used as leaving groups in bimolecular reactions, limiting their applicability in other types of reactions. Additionally, tosylates may not be suitable for certain functional groups or substrates that are sensitive to the harsh reaction conditions required for tosylate conversions.