Often when a molecule contains two functional groups, particularly if the groups

Question

Often when a molecule contains two functional groups, particularly if the groups are similar, both of 1h react and side products are formed. In this reaction, there are two chlorme atoms in chloroacetyl chloride In principle, either chlorine could undergo nucleophilic attack the 2,6-xylidine. However, only the y chloride reacts with the 2,6-xylidene. Explain why the acyl chloride is more reactive than the primary chloride toward nucleophilic substitution. Would it be possible to prepare the amine portion from the reaction of diethylamine with chloroacetic acid first then convert it to the acid chloride for later reaction with the 2,6-xylidene? If so, are there any precautions or key steps that need to be taken into account. If not, why would the sequence not be effective? With the exception of lidocaine, all of the anesthetics in Table 1 undergo fairly rapid hydrolysis in the body Suggest two distinct reasons why lidocaine is relatively resistant to hydrolysis. (Consider the functionafgroups involved and the portion of the molecule where hydrolysis would take place.)

Explanation / Answer

Acyl carbocation is more stable than the primary carbocation so it will formed and the acyl substitution is more faster than the alkyl substitution.

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