Orgo 1 - Addition Reactions
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38 Terms
What is the general mechanism for an addition reaction?
What is Markonikov’s Rule
What is the chirality of a standard addition reaction on an alkene?
Carbene reaction mechanism, and when they happen
1. Dihalocarbenes from haloforms
Reagents like CHCl₃ + strong base (e.g., OH⁻) generate :CCl₂
This carbene adds to an alkene → dichlorocyclopropane
👉 Key signal: CHCl₃ / base or similar haloform conditions
2. Simmons–Smith reaction (carbenoid, not free carbene)
Reagents: CH₂I₂ + Zn(Cu)
Forms a “carbenoid” that behaves like :CH₂
Adds to alkenes → cyclopropane
👉 Key signal: CH₂I₂ + Zn(Cu)
One common mechanism of carbene formation
Mechanism of carbene reaction
Carbenoid (Smith-Simmons)
Regular halogenation in alkynes
Hydrogen halide addition
Addition of water to alkynes
Anti Markovnikov with bromine
Ozone and potassium permanganate
Hydrogenation
Three possibilities for hydrogenation
Acid catalyzed hydrolosis
Oxymercuration regiochemistry
Boron hydration
Stereospecific addition of Br2
OsO4 and dilute KMnO4
Hot and basic potassium permanganate
**Same as basic conditions, just carboxylic salt if no acid workup
mCBA and epoxide product
Permanagante cold dilute
What is the order of strength for oxidative cleavage reactions
Addition of HX product
Hydration with water and like base
Hydrogenation products
Halogenation products
Addition of water and halogen
Water takes up the markonikov addition, halogen the anti
Degree of unsaturation formula
Different outcomes of hydration, summarized
Synthesis of trans alkenes for alkynes
Order of oxidation states (may help you remember products for oxidative cleavage)
Common solvent for the ozone one? What determines if the products are aldhydes or ketones?
2 H on alkene → aldehydes, all R groups → ketones
What determines what the products will be for the strongest one? What decides carboxylic acid vs ketone?
Where to put wedges for chiralty of epoxidation?
Properly representing carbene reaction chirality on products?
What happens when you add water and a dihalogen to something, but there is only one possible site for markonikov addition?
