CHEM 210 REACTIONS EXAM
NEWEST QUESTIONS AND ANSWERS
(2023 / 2024) (VERIFIED
ANSWERS)
Describe the mechanism for the electrophilic addition of a strong acid. <
alkene grabs a hydrogen off of a strong acid, forming a carbocation intermediate.
Step 2) The conjugate base of the acid (an anion now) bonds to the open shell carbocation
What is the regioselectivity of electrophilic addition reactions? <
What is Markovnikov regioselectivity? <
by whatever the most stable carbocation intermediate is (resonance > tertiary > secondary >
primary)
Describe the mechanism for the electrophilic addition of a weak acid. <
catalyst will generally be used to protonate the weak acid reagent (but will technically protonate the
strongest base)
Step 1) strongest acid available protonates the alkene
Step 2) the conjugate base of that acid bonds to the carbocation intermediate
Step 3) deprotonation to reform acid and to give neutral product
What is the stereochemistry of an electrophilic addition product? <
because the product is formed through a carbocation intermediate
What are the reagents for electrophilic addition of a strong acid? <
strong acid (pKa < 5)
What are the reagents for electrophilic addition of a weak acid? <
(pKa > 5), and a strong acid catalyst
What is the degree of substitution? <
bonded to (more alkyl groups means more stable)
What reagents are required in a dissolving metal reduction? <
(NH3) as solvent
Provide a summary of dissolving metal reduction <
added to an alkyne to form the E alkene (anti addition)
What is the stereochemistry of the dissolving metal product? <
What reagents are used for a hydrogenation with a poisoned catalyst? <
- Metal (usually Pd)
- Solid Support (BaSO4 or CaCO3)
- Additive (PbO or quinoline)
FACT CHECK THIS IN BOOK
What is the stereochem for hydrogenation with poisoned catalyst? <
forms Z alkene
Provide a summary for what happens in a hydrogenation of an alkyne <
continue to be added until the molecule is fully saturated (one equivalent is added at a time, syn
addition)
What are the reagents for catalyzed hydrogenation? <
Provide a summary for what happens in an epoxidation <
alkene to form an epoxide
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