reagents

• ozonolysis: oxidative cleavage, alkenes (double bonds) to ketones, aldehydes or carboxylic acids using ozone
• alkyne to aldehyde?


  BH3, NaOH, H2O2
• terminal alkyne to alkenyl halide?


  HX, markovnikov
• alkenyl halide to geminal dihalide?


  HX, markovnikov
• alkyne to alkenyl diahlide?


  X2, selectivity: anti
• alkenyl dihalide to tetrahalide?


  X2, selectivity: anti
• terminal alknye to acetylide?


  NaNH2 or BuLi
• acetylide to internal alkyne?


  RX (primary)
• acetylide to alcohol-alkene?


  epoxide, H+
• alkyne to carboxylic acid?


  O3, H2O or H2O2 or KMno4, H+
• alkyne to alkane?


  Pd/C, H2 (2 equiv)
• alkyne to alkene?


  syn: lindlar's catalyst, H2

  anti: Na/NH3
• alkane to alkyne?


  RCC-
• vicinal dihalide to alkyne?


  NaNH2 (2 equiv)
• alkene to vicinal dihalide?


  X2, CCl4
• alkane to thiol/nitrile/azide/sulfide?


  polar aprotic solvent, strong nucleophile
• alkane to alkyl halide?


  X2, hv
• alkene to alkane?


  Pd/C, H2
• alkene to alkyl halide?

  HX markovnikov, HBr hv radical antimarkovnikov
• alkene ot halohydrins?


  X2, H2O selective: anti, markovnikov
• alkene to vicinal diols?


  OsO4, KHSO3, selective: syn or KMnO4, NaOH (cold)
• alkene to cyclopropane?


  Cu/Zn, CH2I2, selective: syn
• alkene to epoxide?


  RCO3H selective: anti, markovnikov
• alkene to ether?


  H2SO4, ROH, markovnikov
• alkene to aldehyde?


  O3, Zn/H2O
• alkene to alcohol?


  H2SO4, H2O Markovnikov

  BH3, NaOH, H2O2 anti markovnikov
• alcohol to alkene?


  H3PO4
• alcohol to ketone?


  Cr2O72-
• ketone to alcohol?


  NaBH4
• aldehyde to alcohol?


  NaBH4, H+
• alcohol to nitrile?


  TsCl, KCN
• alcohol to carboxylic acid?


  heat, distill

  H+/Cr2O72-
• carboxylic acid to alcohol?


  LiAlH4 in dry etherethoxane, H+/H2O
• aldehyde to carboxylic acid?


  heat, reflux

  H+/Cr2O72-
• ester to carboxylic acid?


  H2O
• alkyl halide to ester?


  polar aprotic solvent, RCO2-
• alcohol to alkyl halide?


  NaX, H2SO4 conc
• alkyl halide to alcohol?


  OH-/H2O
• ester to alcohol?


  RMgBr (2 equiv) or LiAlH4
• acid chloride to ester?


  ROH