llow-up questions 1.) Often, when a molecule contains two functional groups, par

Question

llow-up questions 1.) Often, when a molecule contains two functional groups, particularly if the groups are similar, both of them react, and side products are formed. In this reaction, there are two chlorine atoms in chloroacetyl chloride. In principle, either chlorine could undergo nucleophilic attack the 2.6-xylidine. However, only the acyl chloride reacts with the 2,6-xylidene. a. 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 b. effective? 2. 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 functional groups involved and the portion of the molecule where hydrolysis would take place.)

Explanation / Answer

1-a. Yes acyl chloride is reactive because it has more electron deficient carbonyl carbon, which when reacts form unstable tetrahedral intermediate. But primary chloride is small hard nucleophilic character.

1-b . No. Because if chloride attacks carbon has two nucleophiles that is chloride and Amine.chloride has good leaving nature. It has low pka value.

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