Addition Reactions Flashcards
The addition of water (H₂O) to an alkene in the presence of an acid catalyst, forming an alcohol
Acid-catalyzed hydration
The addition of a hydrogen halide (HX, where X = Cl, Br, I) to an alkene, forming an alkyl halide.
Hydrohalogenation
A two-step reaction sequence that achieves Markovnikov addition of water to an alkene without carbocation rearrangements.
Oxymercuration-demercuration
A two-step reaction sequence that achieves anti-Markovnikov addition of water to an alkene.
Hydroboration-oxidation
The addition of hydrogen (H₂) to an alkene in the presence of a metal catalyst (e.g., Pd, Pt, Ni), forming an alkane
Catalytic hydrogenation
The addition of a halogen (Cl₂, Br₂) to an alkene, forming a vicinal dihalide (two halogens on adjacent carbons).
Halogenation
The addition of a halogen and a hydroxyl group (OH) to an alkene, forming a halohydrin. This reaction occurs when the halogenation is carried out in the presence of water. The water molecule acts as a nucleophile and attacks the halonium ion, leading to the formation of a halohydrin.
Halohydrin formation
Typically exothermic (ΔH < 0) due to the formation of stronger sigma bonds from weaker pi bonds.
However, they often result in decreased entropy (ΔS < 0) as two molecules combine to form one.
Addition reactions
Typically endothermic (ΔH > 0) due to the breaking of strong sigma bonds to form weaker pi bonds.
However, they often result in increased entropy (ΔS > 0) as one molecule forms two.
Elimination reactions
_______________ predicts the regiochemistry of addition reactions to alkenes. It states that in the addition of a protic acid (HX) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached, while the halide (X) will attach to the more substituted carbon.
This preference is due to the stability of the intermediate carbocation formed during the reaction. The more substituted carbocation is more stable due to hyperconjugation and inductive effects, leading to the observed regioselectivity.
Markovnikov’s Rule
_______________ describes the regiochemistry of addition reactions to alkenes, where the addition of a hydrogen atom (from a reagent like HBr) occurs at the more substituted carbon of the double bond, and the other atom (e.g., Br) attaches to the less substituted carbon. This is in contrast to the typical Markovnikov addition, where the hydrogen adds to the less substituted carbon.
anti-Markovnikov rule
The addition of two hydroxyl groups (OH) to an alkene with anti stereochemistry, forming a diol (a compound with two alcohol groups).
Anti-dihydroxylation
epoxidation
The addition of two hydroxyl groups (OH) to an alkene with syn stereochemistry, forming a diol.
Syn-dihydroxylation
formation of a cyclic osmate ester
The cleavage of a carbon-carbon double bond by an oxidizing agent, forming two carbonyl compounds (aldehydes or ketones).
Ozonolysis
(oxidative cleavage)
Hydrohalogenation
Hydration acid catalyzed
Oxymercuration-demercuration
- anti addition only
Hydroboration-oxidation
Catalytic Hydrogenation
Halogenation
Halohydrin Formation
Syn dihydroxylation
Ozonolysis
Anti dihydroxylation
epoxidation
anti addition
Markovnikov or Anti-Markovnikov?
Hydroboration
Anti-Markovnikov
Markovnikov or Anti-Markovnikov?
Oxymercuration
Markovnikov
Markovnikov or Anti-Markovnikov?
Hydration acid catalyzed
Markovnikov
Markovnikov or Anti-Markovnikov?
Hydrohalogenation (HX)
Markovnikov
Markovnikov or Anti-Markovnikov?
Halohydrin Formation
Markovnikov
Syn of Anti Addition ONLY?
Hydroboration
Syn