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Markovnikov
H+ added to the less substituted carbon
Anti-markovnikov
H+ added to more substituted carbon
Acid catalyzed hydration of alkene to make alcohol
Easy way to make alcohols, rearrangement is common though
Oxymercuation - demercuration reagents
Hg(OAc)2, H2O
NaBH4, NaOH
Oxymercuation - demercuration overall scheme and rules
Alkene → alcohol
Markovnikov
Anti-addition
Free radical hydrobromination reagents
HBr
H2O2
Free radical hydrobromination scheme, rules
Alkene → primary alykyl halide
Follows Anti-markovnikov
Hydroboration-oxidation reagents
BH3 * THF
H2O2, NaOH
Hydroboration-oxidation scheme and rules
makes alcohol
Anti-markovnikov
Syn-addition
Catalytic hydrogenation - reduction reagents
H2
Pt, Pd
Catalytic hydrogenation - reduction rule
Syn- addition
Syn dihydroxylation reagents
either : 1. OsO4, 2. H2O2
OR: 1. KMnO4, -OH, cold dilute
Syn dihyroxilation makes a
diol (two OH)
Cyclopropanation reaction
Cyclohexene with a carbonyl → cyclohexane with trangle where alkene was with same carbonyl
Cyclopropanation reagents
CH2I2
Zn, CuCl
Syn-addition
Epoxidation, alkene to epoxide, reagents, scheme
mcpBA
syn-addition
Addition of halogen to alkene, halogenation
Br2 (or Cl2), and CCl4
Anti addition
Halohydrin formation
alkene + Br2 and H2O
Anti-addition
Markovnikov OH
Ozonalysis
O3, -78C
(CH3)2S
Makes Ketone/aldehyde
Vicinal dihalide + KOH (molten) makes
internal alkyne
Vicinal dihalide + 1. NaNH2,150C, 2. H2O makes
Terminal alkyne
Terminal alkyne + NaNH2
deprotonatesm makes acetylide anion
Reduction of alkyne to alkane reagents
2H2, Pd
Reduction of alkyne to a cis-alkene reagents
Lindlars catalyst (Pd/BaSO4), H2
Reduction of alkyne to a trans-alkene reagents
Na, NH3(l) known as “dissolving metal reduction”
Addition of halogens to alkyne, reagents, note
2X2, Cl2, Or Br2 makes tetrahalide
Addition of hydrogen halides to alkynes (HCl, HBr, HI) reagents, product, rule
2HX, makes geminal dihalide (halogen on same carbon)
markovnikov
Mercuric ion-catalyzed hydration of alkyne makes
ketone
Mercuric ion-catalyzed hydration of alkyne reagents
HgSO4
H2O, H2SO4
Hydroboration -oxidation of alkyne makes
aldehyde
Hydroboration -oxidation of alkyne reagents
Sia2BH
H2O2, -OH
acid catalyzed ketoenol tautomerization
happens in Mercuric ion-catalyzed hydration of alkyne
follows protonation (acid) then deprotonation (by water)