Addition reactions

Hydrohalogenation (Alkene)

Markovnikov addition of H and X

Acid Catalyzed hydration (Alkene)

Anti-Markovnikov addition of H and OH with reagent H₃O⁺

Hydrogenation - Alkene

Syn addition of H and H with reagents H₂ & Pt

Halogenation (Alkyne - 1 eq)

Addition of X and X (X = Cl or Br) with reagent X₂

Halohydrin formation (Alkene)

Anti addition of OH and X (X = Cl, Br, or I) with OH on more sub. pos. with reagents Br₂ and H₂O

Syn Dihydroxylation (Alkene)

Syn addition of OH and OH with either [KMnO₄, NaOH, Cold] or [NaHSO₃, H₂O]

Catalytic Hydrogenation (Alkenes and Alkynes)

Syn addition of H₂ across pi bond with H₂ (g) and Pd/C

Hydrobromination (Alkene)

Anti-Markovnikov addition of H and Br with reagents HBr, ROOR

Oxymercuration-Demercuration (Alkene)

Markovnikov addition of H and OH with reagents (1) Hg(OA_c)₂ , H₂O (2) NaBH₄ and no carbocation rearrangements

Hydroboration-oxidation (Alkene)

Anti-Markovnikov, syn addition of H and OH with reagents (1) BH₃ (2) H₂O₂, NaOH

Hydroboration-oxidation (Alkyne)

Terminal Alkyne Anti-Markovnikov addition of H and OH to an enol and tautomerized to an aldehyde with reagents (1) R₂BH and (2) H₂O₂, NaOH

Hydrogenation (Alkyne → cis alkene)

Cis alkene addition of H and H with reagents H₂ and Lindlar’s Catalyst or P-2

Hydrogenation (Alkyne → alkane)

Alkane formation from reagents H₂ and Pt

Bromination (Alkene)

Anti addition of Br and Br with reagent Br₂

Anti Dihydroxylation (alkene)

Peroxy acid converts alkene to epoxide and results in a trans-diol with reagents (1) RCO₃H and (2) H₃O⁺

Ozonolysis (alkene)

Cleavage of C=C to yield 2 products with C=O with reagents (1) O₃ and (2) DMS

Ozonolysis (Internal Alkynes)

Cleavage of C≡C resulting in 2 carboxylic acids with reagents (1) O₃ and (2) H₂O

Ozonolysis (Terminal Alkynes)

Cleavage of C≡C resulting in 1 carboxylic acid & 1 carbon dioxide with reagents (1) O₃ and (2) H₂O

Dissolving metal reduction (Internal alkynes)

Trans alkene product from reagents Na, NH₃ (l)

Elimination (Alkyne)

Vicinal or geminal dibromide converted to an alkyne from (1) xs NaNH₂ and (2) H₂O

Hydrohalogenation (Terminal alkyne - 1 eq)

Markovnikov addition to form a vicinal dihalide with reagent HX

Hydrohalogenation (Terminal alkyne - xs)

Markovnikov addition to form a geminal dihalide with reagent HX

Acid-catalyzed hydration (Terminal alkyne)

Anti-Markovnikov addition of H and OH to an enol, tautomerizes to a ketone with reagents H₂SO₄, H₂O, or HgSO₄

Halogenation (Alkyne - xs)

Addition of X and X (X = Cl or Br) to a tetrahalide with reagent X₂

Hydrohalogenation (Internal alkyne)

Markovnikov addition of X and H to produce E and Z isomers with reagent HX