Previously, in reactions that form carbonations we could not clearly predict if SN1 or El

Transcribed Image Text: 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: HCl, 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°, 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 any
elimination reactions.
Mechanism
Alcohol
Acid
Product(s)
H2SO4
`OH
HCI
HO
`CH3
HBr
OH
H2SO4
Но

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