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12<meta property="og:description" content="Ch10 Alcohol, Thiol Reactions    Reaction Reactant Condition Product Overall     Dehydration of alcohol alcohol phosphoric acid H3PO4 alkene, water $\ce{ROH -&gt;[H3PO4] alkene &#43; H2O}$   Alcohol and HX alcohol, hydrogen halide  alkyl halide, water $\ce{ROH &#43; HX -&gt; RX &#43; H2O}$   Alcohol and sulfonate ester TsCl alcohol, sulfonate ester TsCl, ROTs pyridine, NaBr alkyl bromide $\ce{ROH &#43; TsCl -&gt;[pyridine] R-OTs -&gt;[NaBr] RBr}$   Alkoxide and inorganic acid alkoxide, inorganic acid (dimethyl sulfate)  ester, conjugate base $\ce{RO- &#43; (CH3)2SO4 -&gt; ROCH3 &#43; CH3SO4-}$   Alcohol and SOCl2 alcohol, thionyl chloride SOCl2 pyridine alkyl chloride, sulfate dioxide, hydrogen chloride $\ce{ROH &#43; SOCl2 -&gt;[][pyridine]RCl &#43; SO2 &#43; HCl}$   Alcohol and Ph3PBr2 alcohol, triphenylphosphine dibromine Ph3PBr2 DMF alkyl bromide, base $\ce{ROH &#43; Ph3PBr2 -&gt;[][DMF] RBr &#43; Ph3P&#43;O- &#43; HBr}$   Oxidation of secondary 2nd alcohol secondary alcohol, Cr(VI) (PCC)  ketone, Cr(III) $\ce{ROH &#43; Cr(VI) (CrO3, pyridine) -&gt; R=O &#43; Cr(III)}$   Oxidation of primary 1st alcohol primary alcohol Cr2O4- aldehyde, carboxylic acid $\ce{RCH2OH -&gt;[Cr2O4-][H2SO4] RCH=O -&gt;[Cr2O4-][H2SO4] RC-OH=O}$   Controlled oxidation of primary 1st alcohol primary alcohol PCC aldehyde $\ce{RCH2OH -&gt;[PCC][CH2Cl2] RCH=O}$   Oxidation of primary alcohol primary alcohol, potassium permaganate KMnO4  carboxylic acid&rsquo;s conjugate base $\ce{RCH2OH &#43; KMnO4 &#43; OH- -&gt; MnO2 &#43; RCOO- -&gt;[H3O&#43;] RCOOH}$   Oxidation of thiols/disulfide thiols/disulfide, KMnO4/HNO3  sulfonic acid $\ce{RSH -&gt;[HNO3] RSO3H}$   Oxidation of thiols thiol, oxygen O2/iodine I2/bromine Br2  disulfide $\ce{2RSH &#43; I2 &#43; 2NaOH -&gt; RSSR &#43; 2NaI &#43; 2H2O}$    Synthesis of alcohol    Reaction Reactant Condition Product Overall     Hydroboration-oxidation alkene HBR2, H2O2/OH- alcohol $\ce{alkene -&gt;[(1) HBR2][(2) H2O2/OH-] ROH}$   Oxymercuration-reduction alkene Hg(OAc)2/H2O, NaBH2/NaOH alcohol $\ce{alkene -&gt;[(1) Hg(OAc)2/H2O][(2) NaBH2/NaOH] ROH}$   Acid-cayalyzed hydration of alkene alkene, water H2O acid alcohol $\ce{alkene &#43; H2O -&gt;[H3O&#43;] ROH}$    Ch11 Ether, Sulfide, Epoxide, Glycol Synthesis, Cleavage of ether    Reaction Reactant Condition Product Overall     Williamson ether synthesis alcohol NaH, THF ether $\ce{ROH -&gt;[NaH][THF] RO- &#43; Na&#43; &#43; H2 -&gt;[XR&#39;] ROR&#39; &#43; NaX &#43; H2}$   Williamson sulfide synthesis thiol ROTs sulfide $\ce{RSH -&gt;[OH-][CH3OH] RS- &#43; H2O -&gt;[R&rsquo;OTs] RSR&#39; &#43; H2O &#43; OTs-}$   Alkoxymercuration-reduction alkene Hg(OAc)2/HOR, NaBH4 ether $\ce{alkene -&gt;[(1) Hg(OAc)2/HOR&#39;][(2) NaBH4] -&gt; ROR&#39;}$   Primary 1st alcohol dehydration primary alcohol sulfuric acid H2SO4, heat ether, water H2O $\ce{2ROH -&gt;[H2SO4, \Delta] ROR &#43; H2O}$   Tertiary 3rd alcohol dehydration tertiary alcohol, primary alcohol sulfuric acid H2SO4 ester, water H2O $\ce{ROH &#43; R&rsquo;OH -&gt;[dilute H2SO4] ROR&#39; &#43; H2O}$   Alkene addition by tertiary alcohol alkene, tertiary alcohol sulfuric acid H2SO4 ether $\ce{alkene &#43; ROH -&gt;[dilute H2SO4] (CH3)3COR;}$   Ether cleavage ether, hydrogen halide heat alcohol, alkyl halide $\ce{ROR&#39; &#43; HX -&gt;[\Delta] ROH &#43; R&rsquo;X}$    Synthesis of epoxide    Reaction Reactant Condition Product Overall     Oxidation of alkene with RCOOOH alkene, peroxycarboxylic acid RCOOOH (MCPBA)  epoxide, carboxylic acid $\ce{alkene &#43; RCOOOH (MCPBA) -&gt; epoxide &#43; RCOOH}$   Cyclization of halohydrin halohydrin (alcohol &#43; alkyl halide RX), base  epoxide, water H2O $\ce{halohydrin (OH-C-C-X) &#43; NaOH -&gt; epoxide &#43; NaX &#43; H2O}$    Ring opening of epoxide    Reaction Reactant Condition Product Overall     Base ring opening epoxide, alcohol alkoxide alcohol-ether $\ce{epoxide &#43; R&rsquo;OH -&gt;[R&rsquo;O-] ester-alcohol}$   Acid ring opening epoxide, alcohol acid alcohol-ether $\ce{epoxide, R&rsquo;OH -&gt;[H3O&#43;] alcohol-ether}$   Grignard organometallic ring opening Grignard reagent MgBr, epoxide ether, heat, acid H3O&#43; alcohol $\ce{epoxide &#43; R&rsquo;MgBr -&gt;[(1) ether, heat][H3O&#43;] R&rsquo;CR2CR2OH}$    Preparation, Cleavage of glycol    Reaction Reactant Condition Product Overall     Acid ring opening (hydrolysis) of epoxide epoxide, water H2O acid glycol $\ce{epoxide &#43; H2O -&gt;[acid] glycol}$   Oxidation of alkene by OsO4 alkene, osmium tetroxide OsO4 water H2O, NaHSO3 glycol $\ce{R2C=CR2 &#43; OsO4 -&gt;[H2O][NaHSO3] glycol &#43; OsO3(OH)2}$   Alkene &#43; KMnO4 alkene, potassium permanganate KMnO4 water, acetone glycol, MnO2 $\ce{alkene &#43; KMnO4 -&gt;[H2O, OH-][acetone] glycol &#43; MnO2}$   Glycol cleavage glycol, periodic acid H5IO6 HOAc aldehyde, ketone, water $\ce{glycol &#43; H5IO6 -&gt;[HOAc] R&#39;-CH=O &#43; R-CR=O &#43; 2H2O &#43; HIO3H2O}$    Oxonium salt    Reaction Reactant Condition Product Overall     Oxonium salt nucleophile, oxonium salt  alcohol $\ce{Nu- &#43; R3O&#43; -&gt; ROH &#43; H2O}
12$    Ch14 Alkyne Reactions    Reaction Reactant Condition Product Overall     Alkyne addition alkyne, hydrogen halide  alkene halide $\ce{C#C &#43; HX -&gt; XC=C}$   Hydration of alkyne alkyne, water mercury ion, sulfuric acid H2SO4 ketone $\ce{RC#CH &#43; H2O -&gt;[Hg^2&#43;, H2SO4] RC=OCH3}$   Hydroboration-oxidation of symmetric alkyne symmetric alkyne borane BH3, THF, hydrogen peroxide ketone $\ce{R-C#C-R -&gt;[(1) BH3/THF][(2) H2O2/OH-] R-CH2-C=O-R}$   Hydroboration-oxidation of asymmetric alkyne asymmetric 1-alkyne disiamylborane, THF, hydrogen peroxide aldehyde $\ce{R-C#C-H -&gt;[(1) (branch)2BH/THF][(2) H2O2/OH-] R-CH2-C=O-H}$   Catalytic hydrogenation of alkyne alkyne hydrogen gas H2, catalyst cis alkene $\ce{RC=CR -&gt;[H2, catalyst] RCH=HCR}$   Catalytic hydrogenation of alkene alkene hydrogen gas H2, catalyst alkane $\ce{RCH=HCR -&gt;[H2, catalyst] RCH2=H2CR}$   Controlled catalytic hydrogenation of alkyne alkyne Lindlar catalyst/(Pd/C), pyridine cis alkene $\ce{RC=CR -&gt;[Lindlar catalyst Pd/CaCO3 &#43; Pb(OAc)2][or Pd/C, pyridine] RCH=HCR}$   Reduction of alkyne with Na and NH3 alkyne, sodium, liquid ammonia  trans alkene, sodium ion, azanide $\ce{RC=CR &#43; 2Na &#43; 2NH3 -&gt; RCH=HCR &#43; 2Na&#43; &#43; 2NH2-}$   Grignard reaction of alkyne 1-alkyne, Grignard reagent THF acetylenic Grignard reagent, hydrocarbon $\ce{RC#CR &#43; R&rsquo;MgBr -&gt;[THF] RC#CMgBr &#43; R&#39;}$   Alkyne in SN2 rxn alkane halide, acetylenic anion  alkyne, halide ion $\ce{RX &#43; C#CR- -&gt; RC#CR &#43; X-}$    Ch15 Diene Reactions    Reaction Reactant Condition Product Overall     Diels-Alder Rxn diene, alkene (dienophile)  ring $\ce{diene &#43; dienophile -&gt; ring}$   Addition of HX to conjugated diene conjugated diene, hydrogen halide  alkene halide $\ce{conj." />
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20<meta name="twitter:description" content="Ch10 Alcohol, Thiol Reactions    Reaction Reactant Condition Product Overall     Dehydration of alcohol alcohol phosphoric acid H3PO4 alkene, water $\ce{ROH -&gt;[H3PO4] alkene &#43; H2O}$   Alcohol and HX alcohol, hydrogen halide  alkyl halide, water $\ce{ROH &#43; HX -&gt; RX &#43; H2O}$   Alcohol and sulfonate ester TsCl alcohol, sulfonate ester TsCl, ROTs pyridine, NaBr alkyl bromide $\ce{ROH &#43; TsCl -&gt;[pyridine] R-OTs -&gt;[NaBr] RBr}$   Alkoxide and inorganic acid alkoxide, inorganic acid (dimethyl sulfate)  ester, conjugate base $\ce{RO- &#43; (CH3)2SO4 -&gt; ROCH3 &#43; CH3SO4-}$   Alcohol and SOCl2 alcohol, thionyl chloride SOCl2 pyridine alkyl chloride, sulfate dioxide, hydrogen chloride $\ce{ROH &#43; SOCl2 -&gt;[][pyridine]RCl &#43; SO2 &#43; HCl}$   Alcohol and Ph3PBr2 alcohol, triphenylphosphine dibromine Ph3PBr2 DMF alkyl bromide, base $\ce{ROH &#43; Ph3PBr2 -&gt;[][DMF] RBr &#43; Ph3P&#43;O- &#43; HBr}$   Oxidation of secondary 2nd alcohol secondary alcohol, Cr(VI) (PCC)  ketone, Cr(III) $\ce{ROH &#43; Cr(VI) (CrO3, pyridine) -&gt; R=O &#43; Cr(III)}$   Oxidation of primary 1st alcohol primary alcohol Cr2O4- aldehyde, carboxylic acid $\ce{RCH2OH -&gt;[Cr2O4-][H2SO4] RCH=O -&gt;[Cr2O4-][H2SO4] RC-OH=O}$   Controlled oxidation of primary 1st alcohol primary alcohol PCC aldehyde $\ce{RCH2OH -&gt;[PCC][CH2Cl2] RCH=O}$   Oxidation of primary alcohol primary alcohol, potassium permaganate KMnO4  carboxylic acid&rsquo;s conjugate base $\ce{RCH2OH &#43; KMnO4 &#43; OH- -&gt; MnO2 &#43; RCOO- -&gt;[H3O&#43;] RCOOH}$   Oxidation of thiols/disulfide thiols/disulfide, KMnO4/HNO3  sulfonic acid $\ce{RSH -&gt;[HNO3] RSO3H}$   Oxidation of thiols thiol, oxygen O2/iodine I2/bromine Br2  disulfide $\ce{2RSH &#43; I2 &#43; 2NaOH -&gt; RSSR &#43; 2NaI &#43; 2H2O}$    Synthesis of alcohol    Reaction Reactant Condition Product Overall     Hydroboration-oxidation alkene HBR2, H2O2/OH- alcohol $\ce{alkene -&gt;[(1) HBR2][(2) H2O2/OH-] ROH}$   Oxymercuration-reduction alkene Hg(OAc)2/H2O, NaBH2/NaOH alcohol $\ce{alkene -&gt;
20[(1) Hg(OAc)2/H2O][(2) NaBH2/NaOH] ROH}$   Acid-cayalyzed hydration of alkene alkene, water H2O acid alcohol $\ce{alkene &#43; H2O -&gt;[H3O&#43;] ROH}$    Ch11 Ether, Sulfide, Epoxide, Glycol Synthesis, Cleavage of ether    Reaction Reactant Condition Product Overall     Williamson ether synthesis alcohol NaH, THF ether $\ce{ROH -&gt;[NaH][THF] RO- &#43; Na&#43; &#43; H2 -&gt;[XR&#39;] ROR&#39; &#43; NaX &#43; H2}$   Williamson sulfide synthesis thiol ROTs sulfide $\ce{RSH -&gt;[OH-][CH3OH] RS- &#43; H2O -&gt;[R&rsquo;OTs] RSR&#39; &#43; H2O &#43; OTs-}$   Alkoxymercuration-reduction alkene Hg(OAc)2/HOR, NaBH4 ether $\ce{alkene -&gt;[(1) Hg(OAc)2/HOR&#39;][(2) NaBH4] -&gt; ROR&#39;}$   Primary 1st alcohol dehydration primary alcohol sulfuric acid H2SO4, heat ether, water H2O $\ce{2ROH -&gt;[H2SO4, \Delta] ROR &#43; H2O}$   Tertiary 3rd alcohol dehydration tertiary alcohol, primary alcohol sulfuric acid H2SO4 ester, water H2O $\ce{ROH &#43; R&rsquo;OH -&gt;[dilute H2SO4] ROR&#39; &#43; H2O}$   Alkene addition by tertiary alcohol alkene, tertiary alcohol sulfuric acid H2SO4 ether $\ce{alkene &#43; ROH -&gt;[dilute H2SO4] (CH3)3COR;}$   Ether cleavage ether, hydrogen halide heat alcohol, alkyl halide $\ce{ROR&#39; &#43; HX -&gt;[\Delta] ROH &#43; R&rsquo;X}$    Synthesis of epoxide    Reaction Reactant Condition Product Overall     Oxidation of alkene with RCOOOH alkene, peroxycarboxylic acid RCOOOH (MCPBA)  epoxide, carboxylic acid $\ce{alkene &#43; RCOOOH (MCPBA) -&gt; epoxide &#43; RCOOH}$   Cyclization of halohydrin halohydrin (alcohol &#43; alkyl halide RX), base  epoxide, water H2O $\ce{halohydrin (OH-C-C-X) &#43; NaOH -&gt; epoxide &#43; NaX &#43; H2O}$    Ring opening of epoxide    Reaction Reactant Condition Product Overall     Base ring opening epoxide, alcohol alkoxide alcohol-ether $\ce{epoxide &#43; R&rsquo;OH -&gt;[R&rsquo;O-] ester-alcohol}$   Acid ring opening epoxide, alcohol acid alcohol-ether $\ce{epoxide, R&rsquo;OH -&gt;[H3O&#43;] alcohol-ether}$   Grignard organometallic ring opening Grignard reagent MgBr, epoxide ether, heat, acid H3O&#43; alcohol $\ce{epoxide &#43; R&rsquo;MgBr -&gt;[(1) ether, heat][H3O&#43;] R&rsquo;CR2CR2OH}$    Preparation, Cleavage of glycol    Reaction Reactant Condition Product Overall     Acid ring opening (hydrolysis) of epoxide epoxide, water H2O acid glycol $\ce{epoxide &#43; H2O -&gt;[acid] glycol}$   Oxidation of alkene by OsO4 alkene, osmium tetroxide OsO4 water H2O, NaHSO3 glycol $\ce{R2C=CR2 &#43; OsO4 -&gt;[H2O][NaHSO3] glycol &#43; OsO3(OH)2}$   Alkene &#43; KMnO4 alkene, potassium permanganate KMnO4 water, acetone glycol, MnO2 $\ce{alkene &#43; KMnO4 -&gt;[H2O, OH-][acetone] glycol &#43; MnO2}$   Glycol cleavage glycol, periodic acid H5IO6 HOAc aldehyde, ketone, water $\ce{glycol &#43; H5IO6 -&gt;[HOAc] R&#39;-CH=O &#43; R-CR=O &#43; 2H2O &#43; HIO3H2O}$    Oxonium salt    Reaction Reactant Condition Product Overall     Oxonium salt nucleophile, oxonium salt  alcohol $\ce{Nu- &#43; R3O&#43; -&gt; ROH &#43; H2O}$    Ch14 Alkyne Reactions    Reaction Reactant Condition Product Overall     Alkyne addition alkyne, hydrogen halide  alkene halide $\ce{C#C &#43; HX -&gt; XC=C}
20$   Hydration of alkyne alkyne, water mercury ion, sulfuric acid H2SO4 ketone $\ce{RC#CH &#43; H2O -&gt;[Hg^2&#43;, H2SO4] RC=OCH3}$   Hydroboration-oxidation of symmetric alkyne symmetric alkyne borane BH3, THF, hydrogen peroxide ketone $\ce{R-C#C-R -&gt;[(1) BH3/THF][(2) H2O2/OH-] R-CH2-C=O-R}$   Hydroboration-oxidation of asymmetric alkyne asymmetric 1-alkyne disiamylborane, THF, hydrogen peroxide aldehyde $\ce{R-C#C-H -&gt;[(1) (branch)2BH/THF][(2) H2O2/OH-] R-CH2-C=O-H}$   Catalytic hydrogenation of alkyne alkyne hydrogen gas H2, catalyst cis alkene $\ce{RC=CR -&gt;[H2, catalyst] RCH=HCR}$   Catalytic hydrogenation of alkene alkene hydrogen gas H2, catalyst alkane $\ce{RCH=HCR -&gt;[H2, catalyst] RCH2=H2CR}$   Controlled catalytic hydrogenation of alkyne alkyne Lindlar catalyst/(Pd/C), pyridine cis alkene $\ce{RC=CR -&gt;[Lindlar catalyst Pd/CaCO3 &#43; Pb(OAc)2][or Pd/C, pyridine] RCH=HCR}$   Reduction of alkyne with Na and NH3 alkyne, sodium, liquid ammonia  trans alkene, sodium ion, azanide $\ce{RC=CR &#43; 2Na &#43; 2NH3 -&gt; RCH=HCR &#43; 2Na&#43; &#43; 2NH2-}$   Grignard reaction of alkyne 1-alkyne, Grignard reagent THF acetylenic Grignard reagent, hydrocarbon $\ce{RC#CR &#43; R&rsquo;MgBr -&gt;[THF] RC#CMgBr &#43; R&#39;}$   Alkyne in SN2 rxn alkane halide, acetylenic anion  alkyne, halide ion $\ce{RX &#43; C#CR- -&gt; RC#CR &#43; X-}$    Ch15 Diene Reactions    Reaction Reactant Condition Product Overall     Diels-Alder Rxn diene, alkene (dienophile)  ring $\ce{diene &#43; dienophile -&gt; ring}$   Addition of HX to conjugated diene conjugated diene, hydrogen halide  alkene halide $\ce{conj."/>
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84        <h1 class="single-title posts-title">CHEM 238 Organic Chemistry</h1>
85
86        <div class="post-meta">
87            <div class="post-meta-line"><i class="far fa-calendar-alt fa-fw"></i>&nbsp;<time datetime="2021-08-17">2021-08-17</time>&nbsp;</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 -&gt;[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 -&gt; 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 -&gt;[pyridine] R-OTs -&gt;[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 -&gt; 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 -&gt;[][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 -&gt;[][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) -&gt; 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 -&gt;[Cr2O4-][H2SO4] RCH=O -&gt;[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 -&gt;[PCC][CH2Cl2] RCH=O}$</td>
192</tr>
193<tr>
194<td>Oxidation of primary alcohol</td>
195<td>primary alcohol, potassium permaganate KMnO4</td>
196<td></td>
197<td>carboxylic acid&rsquo;s conjugate base</td>
198<td>$\ce{RCH2OH + KMnO4 + OH- -&gt; MnO2 + RCOO- -&gt;[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 -&gt;[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 -&gt; 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 -&gt;[(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 -&gt;
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 -&gt;[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 -&gt;[NaH][THF] RO- + Na+ + H2 -&gt;[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 -&gt;[OH-][CH3OH] RS- + H2O -&gt;[R&rsquo;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 -&gt;[(1) Hg(OAc)2/HOR'][(2) NaBH4] -&gt; 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 -&gt;[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&rsquo;OH -&gt;[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 -&gt;[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 -&gt;[\Delta] ROH + R&rsquo;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) -&gt; 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 -&gt; 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&rsquo;OH -&gt;[R&rsquo;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&rsquo;OH -&gt;[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&rsquo;MgBr -&gt;[(1) ether, heat][H3O+] R&rsquo;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 -&gt;[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 -&gt;[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 -&gt;[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 -&gt;[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+ -&gt; 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 -&gt; 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 -&gt;[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 -&gt;[(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 -&gt;[(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 -&gt;[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 -&gt;[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 -&gt;[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 -&gt; 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&rsquo;MgBr -&gt;[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- -&gt; 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 -&gt; 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 -&gt; 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 -&gt;[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 -&gt;[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 -&gt;[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 -&gt;[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 -&gt;[(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 -&gt;[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 -&gt;[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 -&gt;[light hv] PhCH2Br + HBr} \newline \ce{CH3-CH2=CH2 -&gt;[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 -&gt;[heat/light, peroxide][CCl4] PhCH2Br} \newline \ce{CH3-CH2=CH2 + NBS -&gt;[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{-&gt; 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 -&gt;[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 -&gt;[][CH2Cl2] PhCH=O + Mn(OH)2} \newline \ce{H2C=CH-CH2OH + MnO2 -&gt;[][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 -&gt;[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 -&gt;[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 -&gt;[SN1, SN2] no reaction} \newline \ce{PhX + Nu -&gt;[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 -&gt;[][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- -&gt; 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 -&gt;[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 -&gt;[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&rsquo;X + NaOH -&gt;[Pd(OAc)2, PPh3, Na2CO3] RR' + NaBr + B(OH)2}$</td>
732</tr>
733<tr>
734<td>Oxidation of phenol</td>
735<td>phenol -&gt; semiquinone</td>
736<td>Na2Cr2O7, H2SO4</td>
737<td>quinone</td>
738<td>$\ce{Ph(OH)2 -&gt;[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 -&gt;[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 -&gt;[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 -&gt;[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 -&gt;[PhNO2] PhOH-CR=O}$</td>
767</tr>
768</tbody>
769</table>
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