1<!DOCTYPE html> 2<html lang="en"> 3 <head> 4 <meta charset="utf-8"> 5<!-- This site is hosted on Netlify. 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pyridine, NaBr alkyl bromide $\ce{ROH + TsCl ->[pyridine] R-OTs ->[NaBr] RBr}$ Alkoxide and inorganic acid alkoxide, inorganic acid (dimethyl sulfate) ester, conjugate base $\ce{RO- + (CH3)2SO4 -> ROCH3 + CH3SO4-}$ Alcohol and SOCl2 alcohol, thionyl chloride SOCl2 pyridine alkyl chloride, sulfate dioxide, hydrogen chloride $\ce{ROH + SOCl2 ->[][pyridine]RCl + SO2 + HCl}$ Alcohol and Ph3PBr2 alcohol, triphenylphosphine dibromine Ph3PBr2 DMF alkyl bromide, base $\ce{ROH + Ph3PBr2 ->[][DMF] RBr + Ph3P+O- + HBr}$ Oxidation of secondary 2nd alcohol secondary alcohol, Cr(VI) (PCC) ketone, Cr(III) $\ce{ROH + Cr(VI) (CrO3, pyridine) -> R=O + Cr(III)}$ Oxidation of primary 1st alcohol primary alcohol Cr2O4- aldehyde, carboxylic acid $\ce{RCH2OH ->[Cr2O4-][H2SO4] RCH=O ->[Cr2O4-][H2SO4] RC-OH=O}$ Controlled oxidation of primary 1st alcohol primary alcohol PCC aldehyde $\ce{RCH2OH ->[PCC][CH2Cl2] RCH=O}$ Oxidation of primary alcohol primary alcohol, potassium permaganate KMnO4 carboxylic acid’s conjugate base $\ce{RCH2OH + KMnO4 + OH- -> MnO2 + RCOO- ->[H3O+] RCOOH}$ Oxidation of thiols/disulfide thiols/disulfide, KMnO4/HNO3 sulfonic acid $\ce{RSH ->[HNO3] RSO3H}$ Oxidation of thiols thiol, oxygen O2/iodine I2/bromine Br2 disulfide $\ce{2RSH + I2 + 2NaOH -> RSSR + 2NaI + 2H2O}$ Synthesis of alcohol Reaction Reactant Condition Product Overall Hydroboration-oxidation alkene HBR2, H2O2/OH- alcohol $\ce{alkene ->[(1) HBR2][(2) H2O2/OH-] ROH}$ Oxymercuration-reduction alkene Hg(OAc)2/H2O, NaBH2/NaOH alcohol $\ce{alkene ->[(1) Hg(OAc)2/H2O][(2) NaBH2/NaOH] ROH}$ Acid-cayalyzed hydration of alkene alkene, water H2O acid alcohol $\ce{alkene + H2O ->[H3O+] ROH}$ Ch11 Ether, Sulfide, Epoxide, Glycol Synthesis, Cleavage of ether Reaction Reactant Condition Product Overall Williamson ether synthesis alcohol NaH, THF ether $\ce{ROH ->[NaH][THF] RO- + Na+ + H2 ->[XR'] ROR' + NaX + H2}$ Williamson sulfide synthesis thiol ROTs sulfide $\ce{RSH ->[OH-][CH3OH] RS- + H2O ->[R’OTs] RSR' + H2O + OTs-}$ Alkoxymercuration-reduction alkene Hg(OAc)2/HOR, NaBH4 ether $\ce{alkene ->[(1) Hg(OAc)2/HOR'][(2) NaBH4] -> ROR'}$ Primary 1st alcohol dehydration primary alcohol sulfuric acid H2SO4, heat ether, water H2O $\ce{2ROH ->[H2SO4, \Delta] ROR + H2O}$ Tertiary 3rd alcohol dehydration tertiary alcohol, primary alcohol sulfuric acid H2SO4 ester, water H2O $\ce{ROH + R’OH ->[dilute H2SO4] ROR' + H2O}$ Alkene addition by tertiary alcohol alkene, tertiary alcohol sulfuric acid H2SO4 ether $\ce{alkene + ROH ->[dilute H2SO4] (CH3)3COR;}$ Ether cleavage ether, hydrogen halide heat alcohol, alkyl halide $\ce{ROR' + HX ->[\Delta] ROH + R’X}$ Synthesis of epoxide Reaction Reactant Condition Product Overall Oxidation of alkene with RCOOOH alkene, peroxycarboxylic acid RCOOOH (MCPBA) epoxide, carboxylic acid $\ce{alkene + RCOOOH (MCPBA) -> epoxide + RCOOH}$ Cyclization of halohydrin halohydrin (alcohol + alkyl halide RX), base epoxide, water H2O $\ce{halohydrin (OH-C-C-X) + NaOH -> epoxide + NaX + H2O}$ Ring opening of epoxide Reaction Reactant Condition Product Overall Base ring opening epoxide, alcohol alkoxide alcohol-ether $\ce{epoxide + R’OH ->[R’O-] ester-alcohol}$ Acid ring opening epoxide, alcohol acid alcohol-ether $\ce{epoxide, R’OH ->[H3O+] alcohol-ether}$ Grignard organometallic ring opening Grignard reagent MgBr, epoxide ether, heat, acid H3O+ alcohol $\ce{epoxide + R’MgBr ->[(1) ether, heat][H3O+] R’CR2CR2OH}$ Preparation, Cleavage of glycol Reaction Reactant Condition Product Overall Acid ring opening (hydrolysis) of epoxide epoxide, water H2O acid glycol $\ce{epoxide + H2O ->[acid] glycol}$ Oxidation of alkene by OsO4 alkene, osmium tetroxide OsO4 water H2O, NaHSO3 glycol $\ce{R2C=CR2 + OsO4 ->[H2O][NaHSO3] glycol + OsO3(OH)2}$ Alkene + KMnO4 alkene, potassium permanganate KMnO4 water, acetone glycol, MnO2 $\ce{alkene + KMnO4 ->[H2O, OH-][acetone] glycol + MnO2}$ Glycol cleavage glycol, periodic acid H5IO6 HOAc aldehyde, ketone, water $\ce{glycol + H5IO6 ->[HOAc] R'-CH=O + R-CR=O + 2H2O + HIO3H2O}$ Oxonium salt Reaction Reactant Condition Product Overall Oxonium salt nucleophile, oxonium salt alcohol $\ce{Nu- + R3O+ -> ROH + H2O}
12$ Ch14 Alkyne Reactions Reaction Reactant Condition Product Overall Alkyne addition alkyne, hydrogen halide alkene halide $\ce{C#C + HX -> XC=C}$ Hydration of alkyne alkyne, water mercury ion, sulfuric acid H2SO4 ketone $\ce{RC#CH + H2O ->[Hg^2+, H2SO4] RC=OCH3}$ Hydroboration-oxidation of symmetric alkyne symmetric alkyne borane BH3, THF, hydrogen peroxide ketone $\ce{R-C#C-R ->[(1) BH3/THF][(2) H2O2/OH-] R-CH2-C=O-R}$ Hydroboration-oxidation of asymmetric alkyne asymmetric 1-alkyne disiamylborane, THF, hydrogen peroxide aldehyde $\ce{R-C#C-H ->[(1) (branch)2BH/THF][(2) H2O2/OH-] R-CH2-C=O-H}$ Catalytic hydrogenation of alkyne alkyne hydrogen gas H2, catalyst cis alkene $\ce{RC=CR ->[H2, catalyst] RCH=HCR}$ Catalytic hydrogenation of alkene alkene hydrogen gas H2, catalyst alkane $\ce{RCH=HCR ->[H2, catalyst] RCH2=H2CR}$ Controlled catalytic hydrogenation of alkyne alkyne Lindlar catalyst/(Pd/C), pyridine cis alkene $\ce{RC=CR ->[Lindlar catalyst Pd/CaCO3 + Pb(OAc)2][or Pd/C, pyridine] RCH=HCR}$ Reduction of alkyne with Na and NH3 alkyne, sodium, liquid ammonia trans alkene, sodium ion, azanide $\ce{RC=CR + 2Na + 2NH3 -> RCH=HCR + 2Na+ + 2NH2-}$ Grignard reaction of alkyne 1-alkyne, Grignard reagent THF acetylenic Grignard reagent, hydrocarbon $\ce{RC#CR + R’MgBr ->[THF] RC#CMgBr + R'}$ Alkyne in SN2 rxn alkane halide, acetylenic anion alkyne, halide ion $\ce{RX + C#CR- -> RC#CR + X-}$ Ch15 Diene Reactions Reaction Reactant Condition Product Overall Diels-Alder Rxn diene, alkene (dienophile) ring $\ce{diene + dienophile -> ring}$ Addition of HX to conjugated diene conjugated diene, hydrogen halide alkene halide $\ce{conj." /> 13<meta property="og:type" content="article" /> 14<meta property="og:url" content="https://equation-sheets.netlify.app/chem/chem238/" /><meta property="article:section" content="chem" /> 15<meta property="article:published_time" content="2021-08-17T00:00:00+08:00" /> 16<meta property="article:modified_time" content="2021-08-17T00:00:00+08:00" /> 17 18<meta name="twitter:card" content="summary"/> 19<meta name="twitter:title" content="CHEM 238 Organic Chemistry"/> 20<meta name="twitter:description" content="Ch10 Alcohol, Thiol Reactions Reaction Reactant Condition Product Overall Dehydration of alcohol alcohol phosphoric acid H3PO4 alkene, water $\ce{ROH ->[H3PO4] alkene + H2O}$ Alcohol and HX alcohol, hydrogen halide alkyl halide, water $\ce{ROH + HX -> RX + H2O}$ Alcohol and sulfonate ester TsCl alcohol, sulfonate ester TsCl, ROTs pyridine, NaBr alkyl bromide $\ce{ROH + TsCl ->[pyridine] R-OTs ->[NaBr] RBr}$ Alkoxide and inorganic acid alkoxide, inorganic acid (dimethyl sulfate) ester, conjugate base $\ce{RO- + (CH3)2SO4 -> ROCH3 + CH3SO4-}$ Alcohol and SOCl2 alcohol, thionyl chloride SOCl2 pyridine alkyl chloride, sulfate dioxide, hydrogen chloride $\ce{ROH + SOCl2 ->[][pyridine]RCl + SO2 + HCl}$ Alcohol and Ph3PBr2 alcohol, triphenylphosphine dibromine Ph3PBr2 DMF alkyl bromide, base $\ce{ROH + Ph3PBr2 ->[][DMF] RBr + Ph3P+O- + HBr}$ Oxidation of secondary 2nd alcohol secondary alcohol, Cr(VI) (PCC) ketone, Cr(III) $\ce{ROH + Cr(VI) (CrO3, pyridine) -> R=O + Cr(III)}$ Oxidation of primary 1st alcohol primary alcohol Cr2O4- aldehyde, carboxylic acid $\ce{RCH2OH ->[Cr2O4-][H2SO4] RCH=O ->[Cr2O4-][H2SO4] RC-OH=O}$ Controlled oxidation of primary 1st alcohol primary alcohol PCC aldehyde $\ce{RCH2OH ->[PCC][CH2Cl2] RCH=O}$ Oxidation of primary alcohol primary alcohol, potassium permaganate KMnO4 carboxylic acid’s conjugate base $\ce{RCH2OH + KMnO4 + OH- -> MnO2 + RCOO- ->[H3O+] RCOOH}$ Oxidation of thiols/disulfide thiols/disulfide, KMnO4/HNO3 sulfonic acid $\ce{RSH ->[HNO3] RSO3H}$ Oxidation of thiols thiol, oxygen O2/iodine I2/bromine Br2 disulfide $\ce{2RSH + I2 + 2NaOH -> RSSR + 2NaI + 2H2O}$ Synthesis of alcohol Reaction Reactant Condition Product Overall Hydroboration-oxidation alkene HBR2, H2O2/OH- alcohol $\ce{alkene ->[(1) HBR2][(2) H2O2/OH-] ROH}$ Oxymercuration-reduction alkene Hg(OAc)2/H2O, NaBH2/NaOH alcohol $\ce{alkene ->
20[(1) Hg(OAc)2/H2O][(2) NaBH2/NaOH] ROH}$ Acid-cayalyzed hydration of alkene alkene, water H2O acid alcohol $\ce{alkene + H2O ->[H3O+] ROH}$ Ch11 Ether, Sulfide, Epoxide, Glycol Synthesis, Cleavage of ether Reaction Reactant Condition Product Overall Williamson ether synthesis alcohol NaH, THF ether $\ce{ROH ->[NaH][THF] RO- + Na+ + H2 ->[XR'] ROR' + NaX + H2}$ Williamson sulfide synthesis thiol ROTs sulfide $\ce{RSH ->[OH-][CH3OH] RS- + H2O ->[R’OTs] RSR' + H2O + OTs-}$ Alkoxymercuration-reduction alkene Hg(OAc)2/HOR, NaBH4 ether $\ce{alkene ->[(1) Hg(OAc)2/HOR'][(2) NaBH4] -> ROR'}$ Primary 1st alcohol dehydration primary alcohol sulfuric acid H2SO4, heat ether, water H2O $\ce{2ROH ->[H2SO4, \Delta] ROR + H2O}$ Tertiary 3rd alcohol dehydration tertiary alcohol, primary alcohol sulfuric acid H2SO4 ester, water H2O $\ce{ROH + R’OH ->[dilute H2SO4] ROR' + H2O}$ Alkene addition by tertiary alcohol alkene, tertiary alcohol sulfuric acid H2SO4 ether $\ce{alkene + ROH ->[dilute H2SO4] (CH3)3COR;}$ Ether cleavage ether, hydrogen halide heat alcohol, alkyl halide $\ce{ROR' + HX ->[\Delta] ROH + R’X}$ Synthesis of epoxide Reaction Reactant Condition Product Overall Oxidation of alkene with RCOOOH alkene, peroxycarboxylic acid RCOOOH (MCPBA) epoxide, carboxylic acid $\ce{alkene + RCOOOH (MCPBA) -> epoxide + RCOOH}$ Cyclization of halohydrin halohydrin (alcohol + alkyl halide RX), base epoxide, water H2O $\ce{halohydrin (OH-C-C-X) + NaOH -> epoxide + NaX + H2O}$ Ring opening of epoxide Reaction Reactant Condition Product Overall Base ring opening epoxide, alcohol alkoxide alcohol-ether $\ce{epoxide + R’OH ->[R’O-] ester-alcohol}$ Acid ring opening epoxide, alcohol acid alcohol-ether $\ce{epoxide, R’OH ->[H3O+] alcohol-ether}$ Grignard organometallic ring opening Grignard reagent MgBr, epoxide ether, heat, acid H3O+ alcohol $\ce{epoxide + R’MgBr ->[(1) ether, heat][H3O+] R’CR2CR2OH}$ Preparation, Cleavage of glycol Reaction Reactant Condition Product Overall Acid ring opening (hydrolysis) of epoxide epoxide, water H2O acid glycol $\ce{epoxide + H2O ->[acid] glycol}$ Oxidation of alkene by OsO4 alkene, osmium tetroxide OsO4 water H2O, NaHSO3 glycol $\ce{R2C=CR2 + OsO4 ->[H2O][NaHSO3] glycol + OsO3(OH)2}$ Alkene + KMnO4 alkene, potassium permanganate KMnO4 water, acetone glycol, MnO2 $\ce{alkene + KMnO4 ->[H2O, OH-][acetone] glycol + MnO2}$ Glycol cleavage glycol, periodic acid H5IO6 HOAc aldehyde, ketone, water $\ce{glycol + H5IO6 ->[HOAc] R'-CH=O + R-CR=O + 2H2O + HIO3H2O}$ Oxonium salt Reaction Reactant Condition Product Overall Oxonium salt nucleophile, oxonium salt alcohol $\ce{Nu- + R3O+ -> ROH + H2O}$ Ch14 Alkyne Reactions Reaction Reactant Condition Product Overall Alkyne addition alkyne, hydrogen halide alkene halide $\ce{C#C + HX -> XC=C}
20$ Hydration of alkyne alkyne, water mercury ion, sulfuric acid H2SO4 ketone $\ce{RC#CH + H2O ->[Hg^2+, H2SO4] RC=OCH3}$ Hydroboration-oxidation of symmetric alkyne symmetric alkyne borane BH3, THF, hydrogen peroxide ketone $\ce{R-C#C-R ->[(1) BH3/THF][(2) H2O2/OH-] R-CH2-C=O-R}$ Hydroboration-oxidation of asymmetric alkyne asymmetric 1-alkyne disiamylborane, THF, hydrogen peroxide aldehyde $\ce{R-C#C-H ->[(1) (branch)2BH/THF][(2) H2O2/OH-] R-CH2-C=O-H}$ Catalytic hydrogenation of alkyne alkyne hydrogen gas H2, catalyst cis alkene $\ce{RC=CR ->[H2, catalyst] RCH=HCR}$ Catalytic hydrogenation of alkene alkene hydrogen gas H2, catalyst alkane $\ce{RCH=HCR ->[H2, catalyst] RCH2=H2CR}$ Controlled catalytic hydrogenation of alkyne alkyne Lindlar catalyst/(Pd/C), pyridine cis alkene $\ce{RC=CR ->[Lindlar catalyst Pd/CaCO3 + Pb(OAc)2][or Pd/C, pyridine] RCH=HCR}$ Reduction of alkyne with Na and NH3 alkyne, sodium, liquid ammonia trans alkene, sodium ion, azanide $\ce{RC=CR + 2Na + 2NH3 -> RCH=HCR + 2Na+ + 2NH2-}$ Grignard reaction of alkyne 1-alkyne, Grignard reagent THF acetylenic Grignard reagent, hydrocarbon $\ce{RC#CR + R’MgBr ->[THF] RC#CMgBr + R'}$ Alkyne in SN2 rxn alkane halide, acetylenic anion alkyne, halide ion $\ce{RX + C#CR- -> RC#CR + X-}$ Ch15 Diene Reactions Reaction Reactant Condition Product Overall Diels-Alder Rxn diene, alkene (dienophile) ring $\ce{diene + dienophile -> ring}$ Addition of HX to conjugated diene conjugated diene, hydrogen halide alkene halide $\ce{conj."/> 21<meta name="application-name" content="Equation Sheets"> 22<meta name="apple-mobile-web-app-title" content="Equation Sheets"><link rel="shortcut icon" type="image/x-icon" href="/favicon.ico" /> 23 <link rel="icon" type="image/png" sizes="32x32" href="/favicon-32x32.png"> 24 <link rel="icon" type="image/png" sizes="16x16" href="/favicon-16x16.png"><link rel="apple-touch-icon" sizes="180x180" href="/apple-touch-icon.png"><link rel="manifest" href="/site.webmanifest"><link rel="canonical" href="https://equation-sheets.netlify.app/chem/chem238/" /><link rel="next" href="https://equation-sheets.netlify.app/chem/chem155/" /><link rel="stylesheet" href="/lib/normalize/normalize.min.css"><link rel="stylesheet" href="/css/style.min.css"><link rel="stylesheet" href="/lib/fontawesome-free/all.min.css"><link rel="stylesheet" href="/lib/animate/animate.min.css">
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42 43 44 <div id="mask"></div><div class="wrapper"><header class="desktop" id="header-desktop"> 45 <div class="header-wrapper"> 46 <div class="header-title"> 47 <a href="/" title="Equation Sheets">Equation Sheets</a> 48 </div> 49 <div class="menu"> 50 <div class="menu-inner"><a class="menu-item" href="https://github.com/tengjuilin/equation-sheets" title="GitHub" rel="noopener noreffer" target="_blank"><i class='fab fa-github fa-fw'></i> </a><span class="menu-item delimiter"></span><a href="javascript:void(0);" class="menu-item theme-switch" title="Switch Theme"> 51 <i class="fas fa-adjust fa-fw"></i> 52 </a> 53 </div> 54 </div> 55 </div> 56</header><header class="mobile" id="header-mobile"> 57 <div class="header-container"> 58 <div class="header-wrapper"> 59 <div class="header-title"> 60 <a href="/" title="Equation Sheets">Equation Sheets</a> 61 </div> 62 <div class="menu-toggle" id="menu-toggle-mobile"> 63 <span></span><span></span><span></span> 64 </div> 65 </div> 66 <div 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fa-fw"></i> <time datetime="2021-08-17">2021-08-17</time> </div> 88 </div> 89 90 <div class="details toc" id="toc-static" kept=""> 91 <div class="details-summary toc-title"> 92 <span>Contents</span> 93 <span><i class="details-icon fas fa-angle-right"></i></span> 94 </div> 95 <div class="details-content toc-content" id="toc-content-static"><nav id="TableOfContents"> 96 <ul> 97 <li><a href="#ch10-alcohol-thiol-reactions">Ch10 Alcohol, Thiol Reactions</a> 98 <ul> 99 <li><a href="#synthesis-of-alcohol">Synthesis of alcohol</a></li> 100 </ul> 101 </li> 102 <li><a href="#ch11-ether-sulfide-epoxide-glycol">Ch11 Ether, Sulfide, Epoxide, Glycol</a> 103 <ul> 104 <li><a href="#synthesis-cleavage-of-ether">Synthesis, Cleavage of ether</a></li> 105 <li><a href="#synthesis-of-epoxide">Synthesis of epoxide</a></li> 106 <li><a href="#ring-opening-of-epoxide">Ring opening of epoxide</a></li> 107 <li><a href="#preparation-cleavage-of-glycol">Preparation, Cleavage of glycol</a></li> 108 <li><a href="#oxonium-salt">Oxonium salt</a></li> 109 </ul> 110 </li> 111 <li><a href="#ch14-alkyne-reactions">Ch14 Alkyne Reactions</a></li> 112 <li><a href="#ch15-diene-reactions">Ch15 Diene Reactions</a></li> 113 <li><a href="#ch16-benzene-reactions">Ch16 Benzene Reactions</a></li> 114 <li><a href="#ch17-allylicbenzylic-reactions">Ch17 Allylic/Benzylic Reactions</a></li> 115 <li><a href="#ch18-vinylicaryl-halide-reactions">Ch18 Vinylic/Aryl Halide Reactions</a></li> 116 </ul> 117</nav></div> 118 </div><div class="content" id="content"><h2 id="ch10-alcohol-thiol-reactions">Ch10 Alcohol, Thiol Reactions</h2> 119<table> 120<thead> 121<tr> 122<th>Reaction</th> 123<th>Reactant</th> 124<th>Condition</th> 125<th>Product</th> 126<th>Overall</th> 127</tr> 128</thead> 129<tbody> 130<tr> 131<td>Dehydration of alcohol</td> 132<td>alcohol</td> 133<td>phosphoric acid H3PO4</td> 134<td>alkene, water</td> 135<td>$\ce{ROH ->[H3PO4] alkene + H2O}$</td> 136</tr> 137<tr> 138<td>Alcohol and HX</td> 139<td>alcohol, hydrogen halide</td> 140<td></td> 141<td>alkyl halide, water</td> 142<td>$\ce{ROH + HX -> RX + H2O}$</td> 143</tr> 144<tr> 145<td>Alcohol and sulfonate ester TsCl</td> 146<td>alcohol, sulfonate ester TsCl, ROTs</td> 147<td>pyridine, NaBr</td> 148<td>alkyl bromide</td> 149<td>$\ce{ROH + TsCl ->[pyridine] R-OTs ->[NaBr] RBr}$</td> 150</tr> 151<tr> 152<td>Alkoxide and inorganic acid</td> 153<td>alkoxide, inorganic acid (dimethyl sulfate)</td> 154<td></td> 155<td>ester, conjugate base</td> 156<td>$\ce{RO- + (CH3)2SO4 -> ROCH3 + CH3SO4-}$</td> 157</tr> 158<tr> 159<td>Alcohol and SOCl2</td> 160<td>alcohol, thionyl chloride SOCl2</td> 161<td>pyridine</td> 162<td>alkyl chloride, sulfate dioxide, hydrogen chloride</td> 163<td>$\ce{ROH + SOCl2 ->[][pyridine]RCl + SO2 + HCl}$</td> 164</tr> 165<tr> 166<td>Alcohol and Ph3PBr2</td> 167<td>alcohol, triphenylphosphine dibromine Ph3PBr2</td> 168<td>DMF</td> 169<td>alkyl bromide, base</td> 170<td>$\ce{ROH + Ph3PBr2 ->[][DMF] RBr + Ph3P+O- + HBr}$</td> 171</tr> 172<tr> 173<td>Oxidation of secondary 2nd alcohol</td> 174<td>secondary alcohol, Cr(VI) (PCC)</td> 175<td></td> 176<td>ketone, Cr(III)</td> 177<td>$\ce{ROH + Cr(VI) (CrO3, pyridine) -> R=O + Cr(III)}$</td> 178</tr> 179<tr> 180<td>Oxidation of primary 1st alcohol</td> 181<td>primary alcohol</td> 182<td>Cr2O4-</td> 183<td>aldehyde, carboxylic acid</td> 184<td>$\ce{RCH2OH ->[Cr2O4-][H2SO4] RCH=O ->[Cr2O4-][H2SO4] RC-OH=O}$</td> 185</tr> 186<tr> 187<td>Controlled oxidation of primary 1st alcohol</td> 188<td>primary alcohol</td> 189<td>PCC</td> 190<td>aldehyde</td> 191<td>$\ce{RCH2OH ->[PCC][CH2Cl2] RCH=O}$</td> 192</tr> 193<tr> 194<td>Oxidation of primary alcohol</td> 195<td>primary alcohol, potassium permaganate KMnO4</td> 196<td></td> 197<td>carboxylic acid’s conjugate base</td> 198<td>$\ce{RCH2OH + KMnO4 + OH- -> MnO2 + RCOO- ->[H3O+] RCOOH}$</td> 199</tr> 200<tr> 201<td>Oxidation of thiols/disulfide</td> 202<td>thiols/disulfide, KMnO4/HNO3</td> 203<td></td> 204<td>sulfonic acid</td> 205<td>$\ce{RSH ->[HNO3] RSO3H}$</td> 206</tr> 207<tr> 208<td>Oxidation of thiols</td> 209<td>thiol, oxygen O2/iodine I2/bromine Br2</td> 210<td></td> 211<td>disulfide</td> 212<td>$\ce{2RSH + I2 + 2NaOH -> RSSR + 2NaI + 2H2O}$</td> 213</tr> 214</tbody> 215</table> 216<h3 id="synthesis-of-alcohol">Synthesis of alcohol</h3> 217<table> 218<thead> 219<tr> 220<th>Reaction</th> 221<th>Reactant</th> 222<th>Condition</th> 223<th>Product</th> 224<th>Overall</th> 225</tr> 226</thead> 227<tbody> 228<tr> 229<td>Hydroboration-oxidation</td> 230<td>alkene</td> 231<td>HBR2, H2O2/OH-</td> 232<td>alcohol</td> 233<td>$\ce{alkene ->[(1) HBR2][(2) H2O2/OH-] ROH}$</td> 234</tr> 235<tr> 236<td>Oxymercuration-reduction</td> 237<td>alkene</td> 238<td>Hg(OAc)2/H2O, NaBH2/NaOH</td> 239<td>alcohol</td> 240<td>$\ce{alkene ->
240[(1) Hg(OAc)2/H2O][(2) NaBH2/NaOH] ROH}$</td> 241</tr> 242<tr> 243<td>Acid-cayalyzed hydration of alkene</td> 244<td>alkene, water H2O</td> 245<td>acid</td> 246<td>alcohol</td> 247<td>$\ce{alkene + H2O ->[H3O+] ROH}$</td> 248</tr> 249</tbody> 250</table> 251<h2 id="ch11-ether-sulfide-epoxide-glycol">Ch11 Ether, Sulfide, Epoxide, Glycol</h2> 252<h3 id="synthesis-cleavage-of-ether">Synthesis, Cleavage of ether</h3> 253<table> 254<thead> 255<tr> 256<th>Reaction</th> 257<th>Reactant</th> 258<th>Condition</th> 259<th>Product</th> 260<th>Overall</th> 261</tr> 262</thead> 263<tbody> 264<tr> 265<td>Williamson ether synthesis</td> 266<td>alcohol</td> 267<td>NaH, THF</td> 268<td>ether</td> 269<td>$\ce{ROH ->[NaH][THF] RO- + Na+ + H2 ->[XR'] ROR' + NaX + H2}$</td> 270</tr> 271<tr> 272<td>Williamson sulfide synthesis</td> 273<td>thiol</td> 274<td>ROTs</td> 275<td>sulfide</td> 276<td>$\ce{RSH ->[OH-][CH3OH] RS- + H2O ->[R’OTs] RSR' + H2O + OTs-}$</td> 277</tr> 278<tr> 279<td>Alkoxymercuration-reduction</td> 280<td>alkene</td> 281<td>Hg(OAc)2/HOR, NaBH4</td> 282<td>ether</td> 283<td>$\ce{alkene ->[(1) Hg(OAc)2/HOR'][(2) NaBH4] -> ROR'}$</td> 284</tr> 285<tr> 286<td>Primary 1st alcohol dehydration</td> 287<td>primary alcohol</td> 288<td>sulfuric acid H2SO4, heat</td> 289<td>ether, water H2O</td> 290<td>$\ce{2ROH ->[H2SO4, \Delta] ROR + H2O}$</td> 291</tr> 292<tr> 293<td>Tertiary 3rd alcohol dehydration</td> 294<td>tertiary alcohol, primary alcohol</td> 295<td>sulfuric acid H2SO4</td> 296<td>ester, water H2O</td> 297<td>$\ce{ROH + R’OH ->[dilute H2SO4] ROR' + H2O}$</td> 298</tr> 299<tr> 300<td>Alkene addition by tertiary alcohol</td> 301<td>alkene, tertiary alcohol</td> 302<td>sulfuric acid H2SO4</td> 303<td>ether</td> 304<td>$\ce{alkene + ROH ->[dilute H2SO4] (CH3)3COR;}$</td> 305</tr> 306<tr> 307<td>Ether cleavage</td> 308<td>ether, hydrogen halide</td> 309<td>heat</td> 310<td>alcohol, alkyl halide</td> 311<td>$\ce{ROR' + HX ->[\Delta] ROH + R’X}$</td> 312</tr> 313</tbody> 314</table> 315<h3 id="synthesis-of-epoxide">Synthesis of epoxide</h3> 316<table> 317<thead> 318<tr> 319<th>Reaction</th> 320<th>Reactant</th> 321<th>Condition</th> 322<th>Product</th> 323<th>Overall</th> 324</tr> 325</thead> 326<tbody> 327<tr> 328<td>Oxidation of alkene with RCOOOH</td> 329<td>alkene, peroxycarboxylic acid RCOOOH (MCPBA)</td> 330<td></td> 331<td>epoxide, carboxylic acid</td> 332<td>$\ce{alkene + RCOOOH (MCPBA) -> epoxide + RCOOH}$</td> 333</tr> 334<tr> 335<td>Cyclization of halohydrin</td> 336<td>halohydrin (alcohol + alkyl halide RX), base</td> 337<td></td> 338<td>epoxide, water H2O</td> 339<td>$\ce{halohydrin (OH-C-C-X) + NaOH -> epoxide + NaX + H2O}$</td> 340</tr> 341</tbody> 342</table> 343<h3 id="ring-opening-of-epoxide">Ring opening of epoxide</h3> 344<table> 345<thead> 346<tr> 347<th>Reaction</th> 348<th>Reactant</th> 349<th>Condition</th> 350<th>Product</th> 351<th>Overall</th> 352</tr> 353</thead> 354<tbody> 355<tr> 356<td>Base ring opening</td> 357<td>epoxide, alcohol</td> 358<td>alkoxide</td> 359<td>alcohol-ether</td> 360<td>$\ce{epoxide + R’OH ->[R’O-] ester-alcohol}$</td> 361</tr> 362<tr> 363<td>Acid ring opening</td> 364<td>epoxide, alcohol</td> 365<td>acid</td> 366<td>alcohol-ether</td> 367<td>$\ce{epoxide, R’OH ->[H3O+] alcohol-ether}$</td> 368</tr> 369<tr> 370<td>Grignard organometallic ring opening</td> 371<td>Grignard reagent MgBr, epoxide</td> 372<td>ether, heat, acid H3O+</td> 373<td>alcohol</td> 374<td>$\ce{epoxide + R’MgBr ->[(1) ether, heat][H3O+] R’CR2CR2OH}$</td> 375</tr> 376</tbody> 377</table> 378<h3 id="preparation-cleavage-of-glycol">Preparation, Cleavage of glycol</h3> 379<table> 380<thead> 381<tr> 382<th>Reaction</th> 383<th>Reactant</th> 384<th>Condition</th> 385<th>Product</th> 386<th>Overall</th> 387</tr> 388</thead> 389<tbody> 390<tr> 391<td>Acid ring opening (hydrolysis) of epoxide</td> 392<td>epoxide, water H2O</td> 393<td>acid</td> 394<td>glycol</td> 395<td>$\ce{epoxide + H2O ->[acid] glycol}$</td> 396</tr> 397<tr> 398<td>Oxidation of alkene by OsO4</td> 399<td>alkene, osmium tetroxide OsO4</td> 400<td>water H2O, NaHSO3</td> 401<td>glycol</td> 402<td>$\ce{R2C=CR2 + OsO4 ->[H2O][NaHSO3] glycol + OsO3(OH)2}$</td> 403</tr> 404<tr> 405<td>Alkene + KMnO4</td> 406<td>alkene, potassium permanganate KMnO4</td> 407<td>water, acetone</td> 408<td>glycol, MnO2</td> 409<td>$\ce{alkene + KMnO4 ->[H2O, OH-][acetone] glycol + MnO2}$</td> 410</tr> 411<tr> 412<td>Glycol cleavage</td> 413<td>glycol, periodic acid H5IO6</td> 414<td>HOAc</td> 415<td>aldehyde, ketone, water</td> 416<td>$\ce{glycol + H5IO6 ->[HOAc] R'-CH=O + R-CR=O + 2H2O + HIO3H2O}$</td> 417</tr> 418</tbody> 419</table> 420<h3 id="oxonium-salt">Oxonium salt</h3> 421<table> 422<thead> 423<tr> 424<th>Reaction</th> 425<th>Reactant</th> 426<th>Condition</th> 427<th>Product</th> 428<th>Overall</th> 429</tr> 430</thead> 431<tbody> 432<tr> 433<td>Oxonium salt</td> 434<td>nucleophile, oxonium salt</td> 435<td></td> 436<td>alcohol</td> 437<td>$\ce{Nu- + R3O+ -> ROH + H2O}$</td> 438</tr> 439</tbody> 440</table> 441<h2 id="ch14-alkyne-reactions">Ch14 Alkyne Reactions</h2> 442<table> 443<thead> 444<tr> 445<th>Reaction</th> 446<th>Reactant</th> 447<th>Condition</th> 448<th>Product</th> 449<th>Overall</th> 450</tr> 451</thead> 452<tbody> 453<tr> 454<td>Alkyne addition</td> 455<td>alkyne, hydrogen halide</td> 456<td></td> 457<td>alkene halide</td> 458<td>$\ce{C#C + HX -> XC=C}
458$</td> 459</tr> 460<tr> 461<td>Hydration of alkyne</td> 462<td>alkyne, water</td> 463<td>mercury ion, sulfuric acid H2SO4</td> 464<td>ketone</td> 465<td>$\ce{RC#CH + H2O ->[Hg^2+, H2SO4] RC=OCH3}$</td> 466</tr> 467<tr> 468<td>Hydroboration-oxidation of symmetric alkyne</td> 469<td>symmetric alkyne</td> 470<td>borane BH3, THF, hydrogen peroxide</td> 471<td>ketone</td> 472<td>$\ce{R-C#C-R ->[(1) BH3/THF][(2) H2O2/OH-] R-CH2-C=O-R}$</td> 473</tr> 474<tr> 475<td>Hydroboration-oxidation of asymmetric alkyne</td> 476<td>asymmetric 1-alkyne</td> 477<td>disiamylborane, THF, hydrogen peroxide</td> 478<td>aldehyde</td> 479<td>$\ce{R-C#C-H ->[(1) (branch)2BH/THF][(2) H2O2/OH-] R-CH2-C=O-H}$</td> 480</tr> 481<tr> 482<td>Catalytic hydrogenation of alkyne</td> 483<td>alkyne</td> 484<td>hydrogen gas H2, catalyst</td> 485<td>cis alkene</td> 486<td>$\ce{RC=CR ->[H2, catalyst] RCH=HCR}$</td> 487</tr> 488<tr> 489<td>Catalytic hydrogenation of alkene</td> 490<td>alkene</td> 491<td>hydrogen gas H2, catalyst</td> 492<td>alkane</td> 493<td>$\ce{RCH=HCR ->[H2, catalyst] RCH2=H2CR}$</td> 494</tr> 495<tr> 496<td>Controlled catalytic hydrogenation of alkyne</td> 497<td>alkyne</td> 498<td>Lindlar catalyst/(Pd/C), pyridine</td> 499<td>cis alkene</td> 500<td>$\ce{RC=CR ->[Lindlar catalyst Pd/CaCO3 + Pb(OAc)2][or Pd/C, pyridine] RCH=HCR}$</td> 501</tr> 502<tr> 503<td>Reduction of alkyne with Na and NH3</td> 504<td>alkyne, sodium, liquid ammonia</td> 505<td></td> 506<td>trans alkene, sodium ion, azanide</td> 507<td>$\ce{RC=CR + 2Na + 2NH3 -> RCH=HCR + 2Na+ + 2NH2-}$</td> 508</tr> 509<tr> 510<td>Grignard reaction of alkyne</td> 511<td>1-alkyne, Grignard reagent</td> 512<td>THF</td> 513<td>acetylenic Grignard reagent, hydrocarbon</td> 514<td>$\ce{RC#CR + R’MgBr ->[THF] RC#CMgBr + R'}$</td> 515</tr> 516<tr> 517<td>Alkyne in SN2 rxn</td> 518<td>alkane halide, acetylenic anion</td> 519<td></td> 520<td>alkyne, halide ion</td> 521<td>$\ce{RX + C#CR- -> RC#CR + X-}$</td> 522</tr> 523</tbody> 524</table> 525<h2 id="ch15-diene-reactions">Ch15 Diene Reactions</h2> 526<table> 527<thead> 528<tr> 529<th>Reaction</th> 530<th>Reactant</th> 531<th>Condition</th> 532<th>Product</th> 533<th>Overall</th> 534</tr> 535</thead> 536<tbody> 537<tr> 538<td>Diels-Alder Rxn</td> 539<td>diene, alkene (dienophile)</td> 540<td></td> 541<td>ring</td> 542<td>$\ce{diene + dienophile -> ring}$</td> 543</tr> 544<tr> 545<td>Addition of HX to conjugated diene</td> 546<td>conjugated diene, hydrogen halide</td> 547<td></td> 548<td>alkene halide</td> 549<td>$\ce{conj. diene + HX -> mixed alkene halide}$</td> 550</tr> 551</tbody> 552</table> 553<h2 id="ch16-benzene-reactions">Ch16 Benzene Reactions</h2> 554<table> 555<thead> 556<tr> 557<th>Reaction</th> 558<th>Reactant</th> 559<th>Condition</th> 560<th>Product</th> 561<th>Overall</th> 562</tr> 563</thead> 564<tbody> 565<tr> 566<td>Halogenation of benzene</td> 567<td>benzene, halide gas X2</td> 568<td>iron/iron(iii) bromide FeBr3</td> 569<td>benzene halide, hydrogen halide</td> 570<td>$\ce{Ph + X2 ->[FeBr3/Fe] PhX + HX}$</td> 571</tr> 572<tr> 573<td>Nitration of benzene</td> 574<td>benzene, nitric acid HNO3</td> 575<td>sulfuric acid H2SO4</td> 576<td>nitrobenzene, water</td> 577<td>$\ce{Ph + HNO3 ->[H2SO4] PhNO2 + H2O}$</td> 578</tr> 579<tr> 580<td>Sulfonation of benzene</td> 581<td>benzene, sulfur trioxide</td> 582<td>fuming sulfuric acid H2SO4</td> 583<td>benzenesulfuric acid</td> 584<td>$\ce{Ph + SO3 ->[fuming H2SO4] PhSO3H}$</td> 585</tr> 586<tr> 587<td>Friedel-Crafts alkylation of benzene</td> 588<td>benzene, alkyl chloride</td> 589<td>aluminum chloride AlCl3</td> 590<td>alkyl benzene, hydrogen chloride</td> 591<td>$\ce{Ph + RCl ->[AlCl3] PhR + HCl}$</td> 592</tr> 593<tr> 594<td>Friedel-Crafts acylation of benzene</td> 595<td>benzene, acyl chloride</td> 596<td>aluminum chloride AlCl3, water</td> 597<td>ketone, hydrogen chloride</td> 598<td>$\ce{Ph + Cl-CR=O ->[(1) AlCl3][(2)H2)] Ph-C=OCH3 + HCl}$</td> 599</tr> 600<tr> 601<td>Hydrogenation of benzene</td> 602<td>benzene, hydrogen gas H2</td> 603<td>Ni</td> 604<td>cyclohexane</td> 605<td>$\ce{Ph + 3H2 ->[Ni][175^oC, 180atm] cyclohexane}$</td> 606</tr> 607<tr> 608<td>Hydrogenation of benzene derivatives</td> 609<td>benzene derivative, hydrogen gas H2</td> 610<td>Ni</td> 611<td>substituted cyclohexane</td> 612<td>$\ce{PhR + 3H2 ->[Ni][175^oC, 180atm] cyclohexane-R}$</td> 613</tr> 614</tbody> 615</table> 616<h2 id="ch17-allylicbenzylic-reactions">Ch17 Allylic/Benzylic Reactions</h2> 617<table> 618<thead> 619<tr> 620<th>Reaction</th> 621<th>Reactant</th> 622<th>Condition</th> 623<th>Product</th> 624<th>Overall</th> 625</tr> 626</thead> 627<tbody> 628<tr> 629<td>Radical bromonation of allylic/benzylic hydrogen</td> 630<td>allylic/benzylic species, bromine gas Br2</td> 631<td>light hv</td> 632<td>allylic/benzylic bromide, hydrogen bromide</td> 633<td>$\ce{PhCH3 + Br2 ->[light hv] PhCH2Br + HBr} \newline \ce{CH3-CH2=CH2 ->[light hv] BrCH2-CH2=CH2}$</td> 634</tr> 635<tr> 636<td>Controlled radical bromonation of allylic/benzylic hydrogen</td> 637<td>
637allylic/benzylic species, NBS (N-bromosuccinimide)</td> 638<td>heat/light, peroxide</td> 639<td>allylic/benzylic bromide, succinimide</td> 640<td>$\ce{PhCH3 + NBS ->[heat/light, peroxide][CCl4] PhCH2Br} \newline \ce{CH3-CH2=CH2 + NBS ->[light hv] BrCH2-CH2=CH2 + succinimide}$</td> 641</tr> 642<tr> 643<td>Allylic/benzylic Grignard Reagent</td> 644<td>alkene bromide Br, magnesium Mg</td> 645<td></td> 646<td>alkene, MgBrOH</td> 647<td>$\ce{-> see Ch 17 allylic Grignard reagent}$</td> 648</tr> 649<tr> 650<td>Allylic/benzylic E2 elimination</td> 651<td>allylic/benzylic bromide</td> 652<td>EtOH, Na+, EtO-</td> 653<td>alkene</td> 654<td>$\ce{Ph-CH2CH2-Br ->[Na+, EtO-][EtOH] Ph-CH2CH2-OEt}$</td> 655</tr> 656<tr> 657<td>Oxidation of allylic/benzylic alcohol with MnO2</td> 658<td>allylic/benzylic alcohol, manganese dioxide MnO2</td> 659<td>CH2Cl2</td> 660<td>aldehyde/ketone, Mn(OH)2</td> 661<td>$\ce{PhCH2OH + MnO2 ->[][CH2Cl2] PhCH=O + Mn(OH)2} \newline \ce{H2C=CH-CH2OH + MnO2 ->[][CH2Cl2] H2C=CH-CH2=O + Mn(OH)2}$</td> 662</tr> 663<tr> 664<td>Benzylic oxidation of alkylbenzene</td> 665<td>alkylbenzene</td> 666<td>Cr(VI): Na2CrO7/CrO3; Mn(VII): KMnO4; O2 + catalyst</td> 667<td>benzylic carboxylic acid</td> 668<td>$\ce{PhR ->[Na2CrO7/CrO3][or KMnO4 or O2 + catalyst] PhCOOH}$</td> 669</tr> 670<tr> 671<td>Biosynthesis of terpene</td> 672<td>isopentenyl pyrophosphate IPP, gamma,gamma-dimethylallyl pyrophosphate DMAP</td> 673<td>prenyl transferase</td> 674<td>terpene, HOPP</td> 675<td>$\ce{IPP + DMAP ->[prenyl transferase SN1] terpene, HOPP}$</td> 676</tr> 677</tbody> 678</table> 679<h2 id="ch18-vinylicaryl-halide-reactions">Ch18 Vinylic/Aryl Halide Reactions</h2> 680<table> 681<thead> 682<tr> 683<th>Reaction</th> 684<th>Reactant</th> 685<th>Condition</th> 686<th>Product</th> 687<th>Overall</th> 688</tr> 689</thead> 690<tbody> 691<tr> 692<td>Vinylic/aryl halide under SN1, SN2 conditions</td> 693<td>Vinylic/aryl halide</td> 694<td>SN1, SN2</td> 695<td>no reaction</td> 696<td>$\ce{CH2=CHX + Nu ->[SN1, SN2] no reaction} \newline \ce{PhX + Nu ->[SN1, SN2] no reaction}$</td> 697</tr> 698<tr> 699<td>Elimination of vinylic halide</td> 700<td>vinylic halide, nucleophile (hydroxide)</td> 701<td>harsh conditions, high temp</td> 702<td>vinylic alkyne, bromide, water</td> 703<td>$\ce{Ph-CH=CH-Br + KOH ->[][200^{\circ}C] Ph-C#C-H + KBr + H2O}$</td> 704</tr> 705<tr> 706<td>Nucleophilic aromatic substitution of aryl halide</td> 707<td>nitro aryl halide, nucleophile</td> 708<td></td> 709<td>nitro aryl nucleophile: halide ion</td> 710<td>$\ce{O2N-Ph-X + Nu- -> O2N-Ph-Nu + X-}$</td> 711</tr> 712<tr> 713<td>Heck reaction (aryl)</td> 714<td>aryl bromide/iodide, alkene</td> 715<td>Pd(0) catalyst (Pd(OAc)2, Pd(PPh3)4)</td> 716<td>aryl alkene, hydrogen bromide</td> 717<td>$\ce{PhBr + alkene ->[Pd(0)] Ph-alkene + HBr}$</td> 718</tr> 719<tr> 720<td>Heck reaction (general)</td> 721<td>alkyl halide + alkene</td> 722<td>Pd(0) catalyst (Pd(OAc)2, Pd(PPh3)4)</td> 723<td>alkene, hydrogen bromide</td> 724<td>$\ce{R1X + alkene-R2 ->[PdL4] R1-alkene-R2 + HX}$</td> 725</tr> 726<tr> 727<td>Suzuki coupling</td> 728<td>aryl boronic acid, aryl halide, sodium hydroxide</td> 729<td>Pd(OAc)2, PPh3, Na2CO3</td> 730<td>biaryl compound, NaBr, B(OH)2</td> 731<td>$\ce{RB(OH)2 + R’X + NaOH ->[Pd(OAc)2, PPh3, Na2CO3] RR' + NaBr + B(OH)2}$</td> 732</tr> 733<tr> 734<td>Oxidation of phenol</td> 735<td>phenol -> semiquinone</td> 736<td>Na2Cr2O7, H2SO4</td> 737<td>quinone</td> 738<td>$\ce{Ph(OH)2 ->[Na2Cr2O7, H2SO4] quinone}$</td> 739</tr> 740<tr> 741<td>Bromination of phenol</td> 742<td>phenol, bromine gas</td> 743<td>CCl4, Hbr, water H2O</td> 744<td>phenol bromide</td> 745<td>$\ce{PhOH + nBr2 ->[various conditions] PhOH-Br_n + nHBr}$</td> 746</tr> 747<tr> 748<td>Nitration of phenol</td> 749<td>phenol</td> 750<td>nitric acid HNO3</td> 751<td>nitric phenol</td> 752<td>$\ce{PhOH ->[HNO3] PhOH-NO2 + H2O}$</td> 753</tr> 754<tr> 755<td>Friedel-Crafts alkylation</td> 756<td>phenol, alcohol</td> 757<td>sulfuric acid H2SO4</td> 758<td>alkyl phenol, water H2O</td> 759<td>$\ce{PhOH + ROH ->[H2SO4] RPhOH + H2O}$</td> 760</tr> 761<tr> 762<td>Friedel-Crafts acylation</td> 763<td>phenol, AlCl3, acyl chloride</td> 764<td>PhNO2</td> 765<td>acyl phenol</td> 766<td>$\ce{PhOH + AlCl3 + RC=O-Cl ->[PhNO2] PhOH-CR=O}$</td> 767</tr> 768</tbody> 769</table> 770</div><div class="post-footer" id="post-footer"> 771 <div class="post-info"> 772 <div class="post-info-line"> 773 <div class="post-info-mod">
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