2. Previously, in reactions that form carbonations we could not clearly predict if SN1 or Elwould be the dominant mechanism. Conversely, we will find that we CAN control whichpathway dominates when an alcohol is present in the electrophile. The dominantmechanism is determined by the acid used to protonate the alcohol and turn it intowater, a good leaving group. A “nucleophilic acid" will force the reaction towardsubstitution, while a "non-nucleophilic acid" will favor elimination.a. Consider the following strong acids: HCl, HI, H2SO4, and HBr. Sort these acids into theappropriate category.Nucleophilic Acidscontain a good NuNon-Nucleophilic Acidshave exceptionally weak conjugate bases(Add heat to promote elimination even more!)b. Based on your classifications of the acids in part a and the type of alcohol given below(methyl, 1°, 2°, or 3°), determine the dominant mechanism that will take place (E1, E2,SN1, or SN2) and draw the major organic product. Add "heat" over the arrow to anyelimination reactions.MechanismAlcoholAcidProduct(s)H2SO4`OHHCIHO`CH3HBrOHH2SO4Но

For a nucleophile to be strong and reactive, its conjugate base must be stable. Out of the given…

2. Previously, in reactions that form carbonations we could not clearly predict if SN1 or El would be the dominant mechanism. Conversely, we will find that we CAN control which pathway dominates when an alcohol is present in the electrophile. The dominant mechanism is determined by the acid used to protonate the alcohol and turn it into water, a good leaving group. A “nucleophilic acid" will force the reaction toward substitution, while a "non-nucleophilic acid" will favor elimination. a. Consider the following strong acids: HCI, HI, H2SO4, and HBr. Sort these acids into the appropriate category. Nucleophilic Acids contain a good Nu Non-Nucleophilic Acids have exceptionally weak conjugate bases (Add heat to promote elimination even more!) b. Based on your classifications of the acids in part a and the type of alcohol given below (methyl, 1°, 2º, or 3°), determine the dominant mechanism that will take place (El, E2, SN1, or SN2) and draw the major organic product. Add "heat" over the arrow to any elimination reactions. Mechanism Alcohol Acid Product(s) H2SO4 HO. HCI НО CH3 HBr H2SO4 HO

2. Previously, in reactions that form carbonations we could not clearly predict if SN1 or El would be the dominant mechanism. Conversely, we will find that we CAN control which pathway dominates when an alcohol is present in the electrophile. The dominant mechanism is determined by the acid used to protonate the alcohol and turn it into water, a good leaving group. A “nucleophilic acid" will force the reaction toward substitution, while a "non-nucleophilic acid" will favor elimination. a. Consider the following strong acids: HCI, HI, H2SO4, and HBr. Sort these acids into the appropriate category. Nucleophilic Acids contain a good Nu Non-Nucleophilic Acids have exceptionally weak conjugate bases (Add heat to promote elimination even more!) b. Based on your classifications of the acids in part a and the type of alcohol given below (methyl, 1°, 2º, or 3°), determine the dominant mechanism that will take place (El, E2, SN1, or SN2) and draw the major organic product. Add "heat" over the arrow to any elimination reactions. Mechanism Alcohol Acid Product(s) H2SO4 HO. HCI НО CH3 HBr H2SO4 HO

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter1: Lewis Structures

Section: Chapter Questions

Problem 63EQ

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The hydrolysis of tert-butyl chloride proceeds less rapidly in a solvent mixture which is 15% water/85% acetone than in one which is 85% water/15% acetone. Why? O The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride. O None of the above. O The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. O The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.
In an E2 mediated elimination reaction of an alkyl halide (H-X) using NaOCH3 as base, which of the following statement is not true? O The reactivity order for alkyl halides (RX) is tertiary secondary> primary. O The rate of reaction = k2 (alkyl halide] [NaOCH₂] O The reaction occurs in a single step. O The rate is independent of the leaving group.
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