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
Chapter1: Lewis Structures
Section: Chapter Questions
Problem 63EQ
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