General anesthetics are compounds that render patients unable to respond to external stimuli and are commonly employed during surgical procedures. Inhaled general anesthetics are either gases or liquid suspensions that are administered and absorbed through the lungs prior to the onset of pharmacologic action. In the 1840s, the organic liquids chloroform and diethyl ether were identified as potent inhaled anesthetics. Despite the observed dangers of acute toxicity associated with chloroform usage and high flammability and addictiveness of diethyl ether, these agents remained in the anesthetic arsenal for over a century.Subsequent studies ultimately led to the discovery of safer anesthetic agents. Empirical evidence demonstrated that anesthetic potency of the (halo)alkanes increased with molecular weight up to a total of 10 carbon atoms. Halogenation of agents increased their stability and capacity for medical storage through the attenuation or elimination of flammability. Shorter-chain methyl ethers were observed to be more effective anesthetics than ethyl ethers, as was the presence of unsaturated functional groups (eg, alkenes, alkynes). The agents halothane, isoflurane, and sevoflurane were developed using the combined body of data and were introduced to the United States market in 1958, 1979, and 1992, respectively. While these newer agents provide a wider margin of safety, an optimal inhaled anesthetic has not yet been discovered.A group of researchers attempting to discover novel inhaled anesthetics wish to perform an SN2 reaction as depicted in Scheme I. The hypothesis of this study is that the product of this reaction will demonstrate improved efficacy as an inhaled anesthetic.Scheme I Question 51If Scheme I is repeated using NaOC(CH3)3 instead of NaOCH3, which of the following statements most accurately describes the outcome of the altered reaction?A.The reaction will occur slower because the electrophile is more sterically hindered.B.The reaction will occur faster because the electrophile is less sterically hindered.C.The reaction will occur faster because the nucleophile is less sterically hindered.D.The reaction will occur slower because the nucleophile is more sterically hindered.
Question
General anesthetics are compounds that render patients unable to respond to external stimuli and are commonly employed during surgical procedures. Inhaled general anesthetics are either gases or liquid suspensions that are administered and absorbed through the lungs prior to the onset of pharmacologic action. In the 1840s, the organic liquids chloroform and diethyl ether were identified as potent inhaled anesthetics. Despite the observed dangers of acute toxicity associated with chloroform usage and high flammability and addictiveness of diethyl ether, these agents remained in the anesthetic arsenal for over a century.Subsequent studies ultimately led to the discovery of safer anesthetic agents. Empirical evidence demonstrated that anesthetic potency of the (halo)alkanes increased with molecular weight up to a total of 10 carbon atoms. Halogenation of agents increased their stability and capacity for medical storage through the attenuation or elimination of flammability. Shorter-chain methyl ethers were observed to be more effective anesthetics than ethyl ethers, as was the presence of unsaturated functional groups (eg, alkenes, alkynes). The agents halothane, isoflurane, and sevoflurane were developed using the combined body of data and were introduced to the United States market in 1958, 1979, and 1992, respectively. While these newer agents provide a wider margin of safety, an optimal inhaled anesthetic has not yet been discovered.A group of researchers attempting to discover novel inhaled anesthetics wish to perform an SN2 reaction as depicted in Scheme I. The hypothesis of this study is that the product of this reaction will demonstrate improved efficacy as an inhaled anesthetic.Scheme I Question 51If Scheme I is repeated using NaOC(CH3)3 instead of NaOCH3, which of the following statements most accurately describes the outcome of the altered reaction?A.The reaction will occur slower because the electrophile is more sterically hindered.B.The reaction will occur faster because the electrophile is less sterically hindered.C.The reaction will occur faster because the nucleophile is less sterically hindered.D.The reaction will occur slower because the nucleophile is more sterically hindered.
Solution
The correct answer is D. The reaction will occur slower because the nucleophile is more sterically hindered.
In an SN2 reaction, the rate of the reaction is influenced by the steric hindrance of the nucleophile. Steric hindrance refers to the interference caused by the size of substituent groups that prevents chemical reactions.
In this case, NaOC(CH3)3 is a bulkier group than NaOCH3, meaning it has more steric hindrance. This increased steric hindrance makes it harder for the nucleophile to approach and react with the electrophile, slowing down the reaction rate. Therefore, if NaOC(CH3)3 is used instead of NaOCH3, the reaction will occur slower due to the increased steric hindrance of the nucleophile.
Similar Questions
Multiple Select QuestionSelect all that applyDiethyl ether came into use as a general anesthetic during the 19th century, but had some drawbacks to its use which caused it to be replaced with more modern anesthetics during the 20th century. What are some of the drawbacks to the use of diethyl ether as an anesthetic? Select all that apply.Multiple select question.High patient mortalityNauseaLack of availabilityFlammability
Select all that applyWhich of the following are properties of diethyl ether as an anesthetic? Select all that apply.Multiple select question.Diethyl ether is not flammable.Diethyl ether has low patient mortality.Diethyl ether causes nausea in many patients.Diethyl ether is safe and easy to administer.
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