Organic Chemistry Chem 202): Top Exam Questions & Answers, 100% Accurate. Verified.

Organic Chemistry Chem 202): Top Exam Questions & Answers, 100% Accurate. Verified. H–Br Markovnikov addition of Br onto more substituted carbon H–Br, ROOR, heat Anti–Markovnikov addition of Br onto least substituted carbon Br2 heat Br Addition to more substituted carbon Br2, H2O2 Br addition to least substituted carbon H2SO4 (aq) Markovnikov addition of OH onto more substituted carbon Hg(OAc)2, H2O, NaBH3, –OH Markovnikov addition of OH onto more substituted carbon 1.BH3*THF, THF 2.H2O2, –OH Anti–Markovnikov addition of OH onto least substituted carbon SN2 NaOH (aq), THF Replaces leaving group (Br) with OH Aldehyde or Ketone "R–" or "H–" +work up Makes an alcohol from the double bond O. Cant have acidic proton around "H–" LiAlH4 (LAH) NaBH4 "R–" MgBr–R Li–R CCR Epoxide to Alcohol "R–" or "H–" +Work Up Opens least substituted carbon R–O–R to Alcohol H–X attacks least substituted carbon except for phenyl or t–Bu Cis Diols KMnO4 cold dilute, –OH OsO4, H2O4 Trans Diols Epoxide Ring NaOH, H2o, H2SO4, H3PO4 Acidic opens more substituted side Basic opens least substituted side Epoxide Ring mCPBA, CH2Cl2 Thionyl Chloride SOCl2, Et3N Replaces OH with Cl PBr3 PI3 Replaces OH with halogen Sulfonate Ester O Cl–S–R O With double bonds to the O (s) Alkoxymercuration–Demurcuration a. Hg(OAc)2, ROH b. NaBH3 Williamson Ether Synthesis SN2 RO– Diol Dehydration H2SO4 (aq) Thioether SMe3 removes H and adds Methyl group onto O Jones Reaction overoxidizes CrO3, H2SO4 (aq), acetone DiChromate overoxidizes NaCr2O7, H2SO4 (aq), acetone PCC stops at aldehyde PCC (CrO2OHCl) NaOAc, CH2CL2