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Why is tert-butoxide often used in elimination reactions when it is not necessary?
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Mark E. Smith
Why is tert-butoxide often used in elimination reactions when it is not necessary?
Generally, it's just because there's a big bottle of $\ce{t-BuOK}$ lying around, so why bother using something else?
In the same range of ideas, I've seen publications where they used $\ce{n-BuLi}$ to deprotonate an alcohol; it's completely overkill, but was probably just more convenient in their case than $\ce{NaH}$ or something else.
Generally, it's just because there's a big bottle of $\ce{t-BuOK}$ lying around, so why bother using something else?
In the same range of ideas, I've seen publications where they used $\ce{n-BuLi}$ to deprotonate an alcohol; it's completely overkill, but was probably just more convenient in their case than $\ce{NaH}$ or something else.
t-BuOK is especially known as a strong base, and a poor nucleophile. Its large, bulky structure causes it to perform exceptionally poorly in substitution, literally eliminating any side reactions when the desired product is the elimination product.
It is easily available, like Raphaël insists.
It's basic strength depends on the medium. It is very strong in DMSO, where the solvent complexates well with $\ce{K+}$ ions. However it is relatively weaker in benzene. This flexibility gives it inevitable popularity.
Many condensation reactions (Stobe's, Darzen's) are seen to have greater yield when t-BuOK is used.
t-BuOK is especially known as a strong base, and a poor nucleophile. Its large, bulky structure causes it to perform exceptionally poorly in substitution, literally eliminating any side reactions when the desired product is the elimination product.
It is easily available, like Raphaël insists.
It's basic strength depends on the medium. It is very strong in DMSO, where the solvent complexates well with $\ce{K+}$ ions. However it is relatively weaker in benzene. This flexibility gives it inevitable popularity.
Many condensation reactions (Stobe's, Darzen's) are seen to have greater yield when t-BuOK is used.
Generally, it's just because there's a big bottle of $\ce{t-BuOK}$ lying around, so why bother using something else?
In the same range of ideas, I've seen publications where they used $\ce{n-BuLi}$ to deprotonate an alcohol; it's completely overkill, but was probably just more convenient in their case than $\ce{NaH}$ or something else.
Generally, it's just because there's a big bottle of $\ce{t-BuOK}$ lying around, so why bother using something else?
In the same range of ideas, I've seen publications where they used $\ce{n-BuLi}$ to deprotonate an alcohol; it's completely overkill, but was probably just more convenient in their case than $\ce{NaH}$ or something else.
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Several reasons:
t-BuOK is especially known as a strong base, and a poor nucleophile. Its large, bulky structure causes it to perform exceptionally poorly in substitution, literally eliminating any side reactions when the desired product is the elimination product.
It is easily available, like Raphaël insists.
It's basic strength depends on the medium. It is very strong in DMSO, where the solvent complexates well with $\ce{K+}$ ions. However it is relatively weaker in benzene. This flexibility gives it inevitable popularity.
Many condensation reactions (Stobe's, Darzen's) are seen to have greater yield when t-BuOK is used.
Several reasons:
t-BuOK is especially known as a strong base, and a poor nucleophile. Its large, bulky structure causes it to perform exceptionally poorly in substitution, literally eliminating any side reactions when the desired product is the elimination product.
It is easily available, like Raphaël insists.
It's basic strength depends on the medium. It is very strong in DMSO, where the solvent complexates well with $\ce{K+}$ ions. However it is relatively weaker in benzene. This flexibility gives it inevitable popularity.
Many condensation reactions (Stobe's, Darzen's) are seen to have greater yield when t-BuOK is used.
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