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Why is the rate of solvolysis of t-butyl chloride lesser than that of 1-chloro-1-methylcyclohexane?
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Posted by
Larry Isaacs
Why is the rate of solvolysis of t-butyl chloride lesser than that of 1-chloro-1-methylcyclohexane?
According to the definition given by The IUPAC Compendium of Chemical Terminology: The Gold Book[1], solvolysis is defined as:
Generally, reaction with a solvent, or with a lyonium ion or lyate ion
involving the rupture of one or more bonds in the reacting solute.
More specifically the term is used for substitution elimination and
fragmentation reactions in which a solvent species is the nucleophile.
It clearly states that elimination occurring due to a solvent is also considered solvolysis and thus elimination in case of t-butyl is also considered.
This means you are right in your reasoning of t-butyl being the most susceptible to solvolysis among the given choices.
I believe this was an error from the question setter. They must have been referring to the substitution reaction due to the solvent but ended up creating a poorly worded question.
Reference:
(1)The IUPAC Compendium of Chemical Terminology: The Gold Book; Gold, V., Ed.; International Union of Pure and Applied Chemistry (IUPAC): Research Triangle Park, NC, 2019.
According to the definition given by The IUPAC Compendium of Chemical Terminology: The Gold Book[1], solvolysis is defined as:
Generally, reaction with a solvent, or with a lyonium ion or lyate ioninvolving the rupture of one or more bonds in the reacting solute.More specifically the term is used for substitution elimination andfragmentation reactions in which a solvent species is the nucleophile.
It clearly states that elimination occurring due to a solvent is also considered solvolysis and thus elimination in case of t-butyl is also considered.
This means you are right in your reasoning of t-butyl being the most susceptible to solvolysis among the given choices.
I believe this was an error from the question setter. They must have been referring to the substitution reaction due to the solvent but ended up creating a poorly worded question.
Reference:
(1)The IUPAC Compendium of Chemical Terminology: The Gold Book; Gold, V., Ed.; International Union of Pure and Applied Chemistry (IUPAC): Research Triangle Park, NC, 2019.
According to the definition given by The IUPAC Compendium of Chemical Terminology: The Gold Book[1], solvolysis is defined as:
It clearly states that elimination occurring due to a solvent is also considered solvolysis and thus elimination in case of t-butyl is also considered.
This means you are right in your reasoning of t-butyl being the most susceptible to solvolysis among the given choices.
I believe this was an error from the question setter. They must have been referring to the substitution reaction due to the solvent but ended up creating a poorly worded question.
Reference:
(1) The IUPAC Compendium of Chemical Terminology: The Gold Book; Gold, V., Ed.; International Union of Pure and Applied Chemistry (IUPAC): Research Triangle Park, NC, 2019.
According to the definition given by The IUPAC Compendium of Chemical Terminology: The Gold Book[1], solvolysis is defined as:
It clearly states that elimination occurring due to a solvent is also considered solvolysis and thus elimination in case of t-butyl is also considered.
This means you are right in your reasoning of t-butyl being the most susceptible to solvolysis among the given choices.
I believe this was an error from the question setter. They must have been referring to the substitution reaction due to the solvent but ended up creating a poorly worded question.
Reference:
(1) The IUPAC Compendium of Chemical Terminology: The Gold Book; Gold, V., Ed.; International Union of Pure and Applied Chemistry (IUPAC): Research Triangle Park, NC, 2019.
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