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H-X Addition to Alkenes
Reagent: H-X (X= Cl, Br, I), Markovnikov Addition
Acid-catalyzed Hydration of Alkenes
Reagent: H3O+ or H2O, H+, Markovnikov Addition
Hydroboration of Alkenes
Reagents: BH3-THF and NaOH, H2O2, syn addition anti-Markovnikov
Halogenation of Alkenes
Reagents: X2 (X= Cl, Br, I) anti-addition of X2
Hydrogenation of Alkenes
Reagents: H2 (D2 for clarity); syn-addition
Epoxidation of Alkenes
Reagent: mCPBA, creates epoxide
Hydrolysis of Epoxides
Reagent: H3O+, anti-ring opening (two OH)
Hydroxylation of Alkenes
Reagents: 1) KMnO4; 2) NaOH, H2O
Oxidative Cleavage of Alkenes
Reagents: 1) KMnO4; 2) H3O+ (two carbonyl groups)
H-X Addition to Dienes
Reagent: H-X (X= Cl, Br, I); Major product = 1,2 addition; Minor product = 1,4 addition
Hydrogenation of Alkenes
Reagent: 1) H2; 2) Pd, Pt, or Ni; produces alkane unless Lindlar Catalyst present (produces (Z)-alkene)
Hydration of Alkynes
Reagents: 1) H3O+; 2) HgSO4, Keto-enol Tautomerism
Formation of Acetylide Anion
Reagents: 1) NaNH2, acid base reaction produces acetylide anion
Reaction of Acetylide Anion with Alkyl Halide and Subsequent Reaction
Reagent: R'-Br; produces alkyne + NaBr
Halogenation
Reagents: 1) X2/FeX3 (X=Cl, Br)
Nitration
Reagent: HNO3, H2SO4
Sulfonation
Reagent: SO3, H2SO4
Alkylation
Reagent: 1)R-Cl; 2) AlCl3 (0.1 Eq)
Acylation
Reagents: 1) Cl-(C=O)-R; 2)AlCl3 (0.1 Eq)