20 Grandmaster 10-Step Organic Conversions | Chemca
Apex Level Synthesis
The absolute pinnacle of chemical logic. These 20 monumental 10-step conversions traverse aliphatic chains to aromatic rings, incorporating profound mechanistic strategies. Designed specifically for elite competitive exam preparation (JEE Advanced / NEET). Click to reveal the intricate architecture of each pathway.
1
Convert Ethanol to m-Bromophenol
Step 1: Halogenation Ethanol is treated with PCl5 to yield Chloroethane.
Step 2: Dehydrohalogenation Chloroethane is heated with alc. KOH to yield Ethene.
Step 3: Bromination Ethene reacts with Br2 in CCl4 to form 1,2-Dibromoethane.
Step 4: Double Elimination The dihalide is heated with NaNH2 to yield Ethyne.
Step 5: Trimerization Ethyne is passed through a red-hot iron tube to form Benzene.
Step 6: Nitration Benzene is nitrated (HNO3/H2SO4) to form Nitrobenzene.
Step 7: Meta-Bromination Nitrobenzene reacts with Br2/FeBr3 to yield m-Bromonitrobenzene.
Step 8: Reduction Reduction with Sn/HCl yields m-Bromoaniline.
Step 9: Diazotization Reaction with NaNO2/HCl (273K) forms the diazonium salt.
Step 10: Hydrolysis Warming the salt with water yields m-Bromophenol.
$$ \begin{gather*}
\ce{CH3CH2OH ->[PCl5] CH3CH2Cl} \\
\ce{CH3CH2Cl ->[KOH (alc)] CH2=CH2} \\
\ce{CH2=CH2 ->[Br2/CCl4] CH2(Br)-CH2(Br)} \\
\ce{CH2(Br)-CH2(Br) ->[NaNH2] HC\equiv CH} \\
\ce{3 HC\equiv CH ->[Fe tube, 873K] C6H6} \\
\ce{C6H6 ->[HNO3/H2SO4] C6H5NO2} \\
\ce{C6H5NO2 ->[Br2/FeBr3] m-Br-C6H4-NO2} \\
\ce{m-Br-C6H4-NO2 ->[Sn/HCl] m-Br-C6H4-NH2} \\
\ce{m-Br-C6H4-NH2 ->[NaNO2/HCl] m-Br-C6H4-N2+Cl-} \\
\ce{m-Br-C6H4-N2+Cl- ->[H2O, \Delta] m-Br-C6H4-OH}
\end{gather*} $$
2
Convert Ethanoic Acid to Propanone
Step 1: Reduction Ethanoic acid is reduced by LiAlH4 to Ethanol.
Step 2: Halogenation Ethanol reacts with SOCl2 to form Chloroethane.
Step 3: Cyanide Step-Up Reaction with KCN yields Propanenitrile.
Step 4: Hydrolysis Acid hydrolysis of the nitrile yields Propanoic acid.
Step 5: Amidation Heating with NH3 yields Propanamide.
Step 6: Hoffmann Step-Down Br2/KOH degrades the amide to Ethanamine.
Step 7: Diazotization HNO2 converts the amine to Ethanol.
Step 8: Mild Oxidation PCC oxidizes Ethanol to Ethanal.
Step 9: Grignard Addition CH3MgBr followed by H3O+ yields Propan-2-ol.
Step 10: Oxidation CrO3 oxidizes the secondary alcohol to Propanone.
$$ \begin{gather*}
\ce{CH3COOH ->[LiAlH4] CH3CH2OH} \\
\ce{CH3CH2OH ->[SOCl2] CH3CH2Cl} \\
\ce{CH3CH2Cl ->[KCN] CH3CH2CN} \\
\ce{CH3CH2CN ->[H3O+] CH3CH2COOH} \\
\ce{CH3CH2COOH ->[NH3, \Delta] CH3CH2CONH2} \\
\ce{CH3CH2CONH2 ->[Br2/KOH] CH3CH2NH2} \\
\ce{CH3CH2NH2 ->[HNO2] CH3CH2OH} \\
\ce{CH3CH2OH ->[PCC] CH3CHO} \\
\ce{CH3CHO ->[1. CH3MgBr][2. H3O+] CH3-CH(OH)-CH3} \\
\ce{CH3-CH(OH)-CH3 ->[CrO3] CH3-CO-CH3}
\end{gather*} $$
3
Convert Propene to Aspirin
Step 1: Bromination Propene + Br2 yields 1,2-Dibromopropane.
Step 2: Double Elimination NaNH2 yields Propyne.
Step 3: Trimerization Red hot Fe tube yields 1,3,5-Trimethylbenzene (Mesitylene).
Step 4: Oxidation KMnO4/H+ oxidizes all methyls to Benzene-1,3,5-tricarboxylic acid.
Step 5: Decarboxylation Soda lime strips carboxyls, yielding Benzene.
Step 6: Chlorination Cl2/FeCl3 yields Chlorobenzene.
Step 7: Dow Process NaOH at 623K yields Sodium phenoxide.
Step 8: Kolbe Reaction CO2 at 400K yields Sodium salicylate.
Step 9: Acidification H+ yields Salicylic acid.
Step 10: Acetylation Acetic anhydride/H+ yields Acetylsalicylic acid (Aspirin).
$$ \begin{gather*}
\ce{CH3-CH=CH2 ->[Br2] CH3-CH(Br)-CH2Br} \\
\ce{CH3-CH(Br)-CH2Br ->[NaNH2] CH3-C\equiv CH} \\
\ce{3 CH3-C\equiv CH ->[Fe tube] 1,3,5-C6H3(CH3)3} \\
\ce{1,3,5-C6H3(CH3)3 ->[KMnO4] 1,3,5-C6H3(COOH)3} \\
\ce{1,3,5-C6H3(COOH)3 ->[NaOH/CaO] C6H6} \\
\ce{C6H6 ->[Cl2/FeCl3] C6H5Cl} \\
\ce{C6H5Cl ->[NaOH, 623K] C6H5ONa} \\
\ce{C6H5ONa ->[CO2, 400K] C6H4(OH)COONa} \\
\ce{C6H4(OH)COONa ->[H+] C6H4(OH)COOH} \\
\ce{C6H4(OH)COOH ->[(CH3CO)2O] C6H4(OCOCH3)COOH}
\end{gather*} $$
4
Convert Benzene to p-Fluorobenzoic Acid
Step 1: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 2: Nitration HNO3/H2SO4 yields p-Nitrotoluene.
Step 3: Reduction Sn/HCl yields p-Toluidine.
Step 4: Diazotization NaNO2/HCl (273K) yields the diazonium salt.
Step 5: Fluoroborate Formation HBF4 precipitates the diazonium fluoroborate.
Step 6: Schiemann Reaction Heating yields p-Fluorotoluene.
Step 7: Side-Chain Halogenation Cl2/uv yields p-Fluorobenzyl chloride.
Step 8: Hydrolysis KOH(aq) yields p-Fluorobenzyl alcohol.
Step 9: Mild Oxidation PCC yields p-Fluorobenzaldehyde.
Step 10: Strong Oxidation KMnO4 yields p-Fluorobenzoic acid.
$$ \begin{gather*}
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[HNO3/H2SO4] p-CH3-C6H4-NO2} \\
\ce{p-CH3-C6H4-NO2 ->[Sn/HCl] p-CH3-C6H4-NH2} \\
\ce{p-CH3-C6H4-NH2 ->[NaNO2/HCl] p-CH3-C6H4-N2+Cl-} \\
\ce{p-CH3-C6H4-N2+Cl- ->[HBF4] p-CH3-C6H4-N2+BF4-} \\
\ce{p-CH3-C6H4-N2+BF4- ->[\Delta] p-CH3-C6H4-F} \\
\ce{p-CH3-C6H4-F ->[Cl2/h\nu] p-F-C6H4-CH2Cl} \\
\ce{p-F-C6H4-CH2Cl ->[KOH (aq)] p-F-C6H4-CH2OH} \\
\ce{p-F-C6H4-CH2OH ->[PCC] p-F-C6H4-CHO} \\
\ce{p-F-C6H4-CHO ->[KMnO4] p-F-C6H4-COOH}
\end{gather*} $$
5
Convert Ethyne to 2,4,6-Tribromoaniline
Step 1: Trimerization Ethyne through red hot Fe tube yields Benzene.
Step 2: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 3: Oxidation KMnO4 oxidizes Toluene to Benzoic acid.
Step 4: Chlorination SOCl2 converts it to Benzoyl chloride.
Step 5: Amidation NH3 yields Benzamide.
Step 6: Hoffmann Degradation Br2/KOH steps it down to Aniline.
Step 7: Diazotization NaNO2/HCl (273K) yields Diazonium salt.
Step 8: Sandmeyer Cyanide CuCN yields Cyanobenzene.
Step 9: Hydrolysis & Hoffmann H3O+ then NH3 then Br2/KOH recreates Aniline (Conceptual loop for steps).
Step 10: Bromination Br2(aq) yields 2,4,6-Tribromoaniline.
$$ \begin{gather*}
\ce{3 HC\equiv CH ->[Fe tube] C6H6} \\
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[KMnO4] C6H5COOH} \\
\ce{C6H5COOH ->[SOCl2] C6H5COCl} \\
\ce{C6H5COCl ->[NH3] C6H5CONH2} \\
\ce{C6H5CONH2 ->[Br2/KOH] C6H5NH2} \\
\ce{C6H5NH2 ->[NaNO2/HCl] C6H5N2+Cl-} \\
\ce{C6H5N2+Cl- ->[CuCN] C6H5CN} \\
\ce{C6H5CN ->[1. H3O+][2. NH3][3. Br2/KOH] C6H5NH2} \\
\ce{C6H5NH2 ->[3Br2(aq)] 2,4,6-C6H2Br3(NH2)}
\end{gather*} $$
6
Convert Benzene to 2-Methylbutan-2-ol
Step 1: Chlorination Cl2/FeCl3 yields Chlorobenzene.
Step 2: Dow Process NaOH(623K)/H+ yields Phenol.
Step 3: Reduction Zn dust yields Benzene.
Step 4: Ozonolysis O3/Zn yields Glyoxal.
Step 5: Reduction LiAlH4 yields Ethane-1,2-diol.
Step 6: Halogenation PBr3 yields 1,2-Dibromoethane.
Step 7: Elimination NaNH2 yields Ethyne.
Step 8: Acetylide Alkylation NaNH2 then CH3I yields Propyne.
Step 9: Hydration H2O/Hg2+ yields Propanone.
Step 10: Grignard EthylMgBr/H+ yields 2-Methylbutan-2-ol.
$$ \begin{gather*}
\ce{C6H6 ->[Cl2/FeCl3] C6H5Cl} \\
\ce{C6H5Cl ->[NaOH(623K)/H+] C6H5OH} \\
\ce{C6H5OH ->[Zn (\Delta)] C6H6} \\
\ce{C6H6 ->[O3 / Zn] 3 O=CH-CH=O} \\
\ce{O=CH-CH=O ->[LiAlH4] HO-CH2-CH2-OH} \\
\ce{HO-CH2-CH2-OH ->[PBr3] Br-CH2-CH2-Br} \\
\ce{Br-CH2-CH2-Br ->[NaNH2] HC\equiv CH} \\
\ce{HC\equiv CH ->[1. NaNH2][2. CH3I] CH3-C\equiv CH} \\
\ce{CH3-C\equiv CH ->[H2O/Hg^2+] CH3-CO-CH3} \\
\ce{CH3-CO-CH3 ->[1. CH3CH2MgBr][2. H+] CH3CH2C(CH3)2OH}
\end{gather*} $$
7
Convert 1-Bromopropane to Lactic Acid
Step 1: Elimination alc KOH yields Propene.
Step 2: Hydration H2O/H+ yields Propan-2-ol.
Step 3: Oxidation CrO3 yields Propanone.
Step 4: Grignard CH3MgBr/H+ yields 2-Methylpropan-2-ol.
Step 5: Dehydration H2SO4(443K) yields 2-Methylpropene.
Step 6: Ozonolysis O3/Zn yields Propanone + Methanal.
Step 7: Grignard on Methanal CH3MgBr/H+ yields Ethanol.
Step 8: Mild Oxidation PCC yields Ethanal.
Step 9: Cyanohydrin HCN yields Ethanal cyanohydrin.
Step 10: Hydrolysis H3O+ yields Lactic Acid.
$$ \begin{gather*}
\ce{CH3CH2CH2Br ->[KOH (alc)] CH3CH=CH2} \\
\ce{CH3CH=CH2 ->[H2O/H+] CH3-CH(OH)-CH3} \\
\ce{CH3-CH(OH)-CH3 ->[CrO3] CH3-CO-CH3} \\
\ce{CH3-CO-CH3 ->[1. CH3MgBr][2. H+] (CH3)3C-OH} \\
\ce{(CH3)3C-OH ->[H2SO4] (CH3)2C=CH2} \\
\ce{(CH3)2C=CH2 ->[O3/Zn] CH3-CO-CH3 + HCHO} \\
\ce{HCHO ->[1. CH3MgBr][2. H+] CH3CH2OH} \\
\ce{CH3CH2OH ->[PCC] CH3CHO} \\
\ce{CH3CHO ->[HCN] CH3-CH(OH)-CN} \\
\ce{CH3-CH(OH)-CN ->[H3O+] CH3-CH(OH)-COOH}
\end{gather*} $$
8
Convert Ethene to m-Nitrobenzyl Cyanide
Step 1: Bromination Br2 yields 1,2-Dibromoethane.
Step 2: Elimination NaNH2 yields Ethyne.
Step 3: Trimerization Fe tube yields Benzene.
Step 4: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 5: Oxidation KMnO4 yields Benzoic acid.
Step 6: Nitration HNO3/H2SO4 yields m-Nitrobenzoic acid.
Step 7: Chlorination SOCl2 yields m-Nitrobenzoyl chloride.
Step 8: Reduction NaBH4 yields m-Nitrobenzyl alcohol.
Step 9: Halogenation PCl5 yields m-Nitrobenzyl chloride.
Step 10: Cyanide KCN yields m-Nitrobenzyl cyanide.
$$ \begin{gather*}
\ce{CH2=CH2 ->[Br2] Br-CH2-CH2-Br} \\
\ce{Br-CH2-CH2-Br ->[NaNH2] HC\equiv CH} \\
\ce{3 HC\equiv CH ->[Fe tube] C6H6} \\
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[KMnO4] C6H5COOH} \\
\ce{C6H5COOH ->[HNO3/H2SO4] m-NO2-C6H4-COOH} \\
\ce{m-NO2-C6H4-COOH ->[SOCl2] m-NO2-C6H4-COCl} \\
\ce{m-NO2-C6H4-COCl ->[NaBH4] m-NO2-C6H4-CH2OH} \\
\ce{m-NO2-C6H4-CH2OH ->[PCl5] m-NO2-C6H4-CH2Cl} \\
\ce{m-NO2-C6H4-CH2Cl ->[KCN] m-NO2-C6H4-CH2CN}
\end{gather*} $$
9
Convert Nitrobenzene to Benzylamine
Step 1: Reduction Sn/HCl yields Aniline.
Step 2: Diazotization NaNO2/HCl yields Diazonium.
Step 3: Deamination H3PO2 yields Benzene.
Step 4: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 5: Halogenation Cl2/hv yields Benzyl chloride.
Step 6: Cyanide KCN yields Benzyl cyanide.
Step 7: Hydrolysis H3O+ yields 2-Phenylethanoic acid.
Step 8: Chlorination SOCl2 yields 2-Phenylethanoyl chloride.
Step 9: Amidation NH3 yields 2-Phenylethanamide.
Step 10: Hoffmann Degradation Br2/KOH steps down to Benzylamine.
$$ \begin{gather*}
\ce{C6H5NO2 ->[Sn/HCl] C6H5NH2} \\
\ce{C6H5NH2 ->[NaNO2/HCl] C6H5N2+Cl-} \\
\ce{C6H5N2+Cl- ->[H3PO2] C6H6} \\
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[Cl2/h\nu] C6H5CH2Cl} \\
\ce{C6H5CH2Cl ->[KCN] C6H5CH2CN} \\
\ce{C6H5CH2CN ->[H3O+] C6H5CH2COOH} \\
\ce{C6H5CH2COOH ->[SOCl2] C6H5CH2COCl} \\
\ce{C6H5CH2COCl ->[NH3] C6H5CH2CONH2} \\
\ce{C6H5CH2CONH2 ->[Br2/KOH] C6H5CH2NH2}
\end{gather*} $$
10
Convert Phenol to cis-But-2-yne
Step 1: Deoxygenation Zn dust yields Benzene.
Step 2: Ozonolysis O3/Zn yields Glyoxal.
Step 3: Reduction LiAlH4 yields Ethane-1,2-diol.
Step 4: Halogenation PBr3 yields 1,2-Dibromoethane.
Step 5: Elimination NaNH2 yields Ethyne.
Step 6: First Acetylide NaNH2 yields Sod. acetylide.
Step 7: Alkylation CH3I yields Propyne.
Step 8: Second Acetylide NaNH2 yields Sod. propynide.
Step 9: Alkylation CH3I yields But-2-yne.
Step 10: Partial Reduction Lindlar's catalyst yields cis-But-2-ene.
$$ \begin{gather*}
\ce{C6H5OH ->[Zn] C6H6} \\
\ce{C6H6 ->[O3/Zn] 3 O=CH-CH=O} \\
\ce{O=CH-CH=O ->[LiAlH4] HO-CH2-CH2-OH} \\
\ce{HO-CH2-CH2-OH ->[PBr3] Br-CH2-CH2-Br} \\
\ce{Br-CH2-CH2-Br ->[NaNH2] HC\equiv CH} \\
\ce{HC\equiv CH ->[NaNH2] HC\equiv CNa} \\
\ce{HC\equiv CNa ->[CH3I] HC\equiv C-CH3} \\
\ce{HC\equiv C-CH3 ->[NaNH2] NaC\equiv C-CH3} \\
\ce{NaC\equiv C-CH3 ->[CH3I] CH3-C\equiv C-CH3} \\
\ce{CH3-C\equiv C-CH3 ->[H2/Lindlar] cis-CH3-CH=CH-CH3}
\end{gather*} $$
11
Convert Chloroethane to p-Iodobenzoic acid
Step 1: Elimination alc KOH yields Ethene.
Step 2: Bromination Br2 yields 1,2-Dibromoethane.
Step 3: Double Elimination NaNH2 yields Ethyne.
Step 4: Trimerization Fe tube yields Benzene.
Step 5: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 6: Nitration HNO3/H2SO4 yields p-Nitrotoluene.
Step 7: Reduction Sn/HCl yields p-Toluidine.
Step 8: Diazotization NaNO2/HCl yields Diazonium.
Step 9: Iodination KI yields p-Iodotoluene.
Step 10: Oxidation KMnO4 yields p-Iodobenzoic acid.
$$ \begin{gather*}
\ce{CH3CH2Cl ->[KOH (alc)] CH2=CH2} \\
\ce{CH2=CH2 ->[Br2] Br-CH2-CH2-Br} \\
\ce{Br-CH2-CH2-Br ->[NaNH2] HC\equiv CH} \\
\ce{3 HC\equiv CH ->[Fe tube] C6H6} \\
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[HNO3/H2SO4] p-CH3-C6H4-NO2} \\
\ce{p-CH3-C6H4-NO2 ->[Sn/HCl] p-CH3-C6H4-NH2} \\
\ce{p-CH3-C6H4-NH2 ->[NaNO2/HCl] p-CH3-C6H4-N2+Cl-} \\
\ce{p-CH3-C6H4-N2+Cl- ->[KI] p-CH3-C6H4-I} \\
\ce{p-CH3-C6H4-I ->[KMnO4] p-I-C6H4-COOH}
\end{gather*} $$
12
Convert Acetone to m-Chloroaniline
Step 1: Reduction LiAlH4 yields Propan-2-ol.
Step 2: Dehydration H2SO4(443K) yields Propene.
Step 3: Bromination Br2 yields 1,2-Dibromopropane.
Step 4: Elimination NaNH2 yields Propyne.
Step 5: Trimerization Fe tube yields Mesitylene.
Step 6: Oxidation KMnO4 yields Trimesic acid.
Step 7: Decarboxylation Soda lime yields Benzene.
Step 8: Nitration HNO3/H2SO4 yields Nitrobenzene.
Step 9: Chlorination Cl2/FeCl3 yields m-Chloronitrobenzene.
Step 10: Reduction Sn/HCl yields m-Chloroaniline.
$$ \begin{gather*}
\ce{CH3-CO-CH3 ->[LiAlH4] CH3-CH(OH)-CH3} \\
\ce{CH3-CH(OH)-CH3 ->[H2SO4] CH3-CH=CH2} \\
\ce{CH3-CH=CH2 ->[Br2] CH3-CH(Br)-CH2Br} \\
\ce{CH3-CH(Br)-CH2Br ->[NaNH2] CH3-C\equiv CH} \\
\ce{3 CH3-C\equiv CH ->[Fe tube] 1,3,5-C6H3(CH3)3} \\
\ce{1,3,5-C6H3(CH3)3 ->[KMnO4] 1,3,5-C6H3(COOH)3} \\
\ce{1,3,5-C6H3(COOH)3 ->[NaOH/CaO] C6H6} \\
\ce{C6H6 ->[HNO3/H2SO4] C6H5NO2} \\
\ce{C6H5NO2 ->[Cl2/FeCl3] m-Cl-C6H4-NO2} \\
\ce{m-Cl-C6H4-NO2 ->[Sn/HCl] m-Cl-C6H4-NH2}
\end{gather*} $$
13
Convert Acetic Acid to Acetophenone
Step 1: Amidation NH3/heat yields Acetamide.
Step 2: Hoffmann Degradation Br2/KOH yields Methylamine.
Step 3: Diazotization HNO2 yields Methanol.
Step 4: Chlorination PCl5 yields Chloromethane.
Step 5: Alkylation Benzene + AlCl3 yields Toluene.
Step 6: Halogenation Cl2/hv yields Benzyl chloride.
Step 7: Hydrolysis KOH(aq) yields Benzyl alcohol.
Step 8: Mild Oxidation PCC yields Benzaldehyde.
Step 9: Grignard CH3MgBr/H+ yields 1-Phenylethanol.
Step 10: Oxidation PCC yields Acetophenone.
$$ \begin{gather*}
\ce{CH3COOH ->[NH3, \Delta] CH3CONH2} \\
\ce{CH3CONH2 ->[Br2/KOH] CH3NH2} \\
\ce{CH3NH2 ->[HNO2] CH3OH} \\
\ce{CH3OH ->[PCl5] CH3Cl} \\
\ce{CH3Cl + C6H6 ->[AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[Cl2/h\nu] C6H5CH2Cl} \\
\ce{C6H5CH2Cl ->[KOH(aq)] C6H5CH2OH} \\
\ce{C6H5CH2OH ->[PCC] C6H5CHO} \\
\ce{C6H5CHO ->[1. CH3MgBr][2. H+] C6H5-CH(OH)-CH3} \\
\ce{C6H5-CH(OH)-CH3 ->[PCC] C6H5-CO-CH3}
\end{gather*} $$
14
Convert 1-Bromopropane to p-Methoxyacetophenone
Step 1: Elimination alc KOH yields Propene.
Step 2: Bromination Br2 yields 1,2-Dibromopropane.
Step 3: Double Elimination NaNH2 yields Propyne.
Step 4: Trimerization Fe tube yields Mesitylene.
Step 5: Oxidation KMnO4 yields Trimesic acid.
Step 6: Decarboxylation Soda lime yields Benzene.
Step 7: Sulfonation Oleum yields Benzenesulfonic acid.
Step 8: Alkali Fusion NaOH(fuse)/H+ yields Phenol.
Step 9: Ether Synthesis CH3I/NaOH yields Anisole.
Step 10: Acylation CH3COCl/AlCl3 yields p-Methoxyacetophenone.
$$ \begin{gather*}
\ce{CH3CH2CH2Br ->[KOH (alc)] CH3CH=CH2} \\
\ce{CH3CH=CH2 ->[Br2] CH3CH(Br)CH2Br} \\
\ce{CH3CH(Br)CH2Br ->[NaNH2] CH3-C\equiv CH} \\
\ce{3 CH3-C\equiv CH ->[Fe tube] 1,3,5-C6H3(CH3)3} \\
\ce{1,3,5-C6H3(CH3)3 ->[KMnO4] 1,3,5-C6H3(COOH)3} \\
\ce{1,3,5-C6H3(COOH)3 ->[Soda lime] C6H6} \\
\ce{C6H6 ->[H2S2O7] C6H5SO3H} \\
\ce{C6H5SO3H ->[NaOH(fuse)/H+] C6H5OH} \\
\ce{C6H5OH ->[NaOH][CH3I] C6H5OCH3} \\
\ce{C6H5OCH3 ->[CH3COCl/AlCl3] p-CH3O-C6H4-COCH3}
\end{gather*} $$
15
Convert Toluene to p-Hydroxybenzamide
Step 1: Nitration HNO3/H2SO4 yields p-Nitrotoluene.
Step 2: Reduction Sn/HCl yields p-Toluidine.
Step 3: Diazotization NaNO2/HCl yields Diazonium.
Step 4: Hydrolysis H2O/heat yields p-Cresol.
Step 5: Protection NaOH/CH3I yields p-Methoxytoluene.
Step 6: Oxidation KMnO4 yields p-Methoxybenzoic acid.
Step 7: Deprotection HI/heat yields p-Hydroxybenzoic acid.
Step 8: Esterification C2H5OH/H+ yields Ethyl p-hydroxybenzoate.
Step 9: Ammonolysis NH3 yields p-Hydroxybenzamide.
Step 10: Alternative SOCl2 then NH3 yields p-Hydroxybenzamide.
$$ \begin{gather*}
\ce{C6H5CH3 ->[HNO3/H2SO4] p-CH3-C6H4-NO2} \\
\ce{p-CH3-C6H4-NO2 ->[Sn/HCl] p-CH3-C6H4-NH2} \\
\ce{p-CH3-C6H4-NH2 ->[NaNO2/HCl] p-CH3-C6H4-N2+Cl-} \\
\ce{p-CH3-C6H4-N2+Cl- ->[H2O, \Delta] p-CH3-C6H4-OH} \\
\ce{p-CH3-C6H4-OH ->[NaOH/CH3I] p-CH3-C6H4-OCH3} \\
\ce{p-CH3-C6H4-OCH3 ->[KMnO4] p-HOOC-C6H4-OCH3} \\
\ce{p-HOOC-C6H4-OCH3 ->[HI, \Delta] p-HOOC-C6H4-OH} \\
\ce{p-HOOC-C6H4-OH ->[SOCl2] p-ClOC-C6H4-OH} \\
\ce{p-ClOC-C6H4-OH ->[NH3] p-H2NOC-C6H4-OH} \\
\text{(Target Achieved)}
\end{gather*} $$
16
Convert Benzene to Butane
Step 1: Chlorination Cl2/FeCl3 yields Chlorobenzene.
Step 2: Dow Process NaOH(623K)/H+ yields Phenol.
Step 3: Reduction Zn dust yields Benzene.
Step 4: Ozonolysis O3/Zn yields Glyoxal.
Step 5: Reduction LiAlH4 yields Ethane-1,2-diol.
Step 6: Halogenation PBr3 yields 1,2-Dibromoethane.
Step 7: Elimination NaNH2 yields Ethyne.
Step 8: Hydrogenation H2/Pd yields Ethene.
Step 9: Hydrohalogenation HBr yields Bromoethane.
Step 10: Wurtz Reaction Na/ether yields Butane.
$$ \begin{gather*}
\ce{C6H6 ->[Cl2/FeCl3] C6H5Cl} \\
\ce{C6H5Cl ->[NaOH(623K)/H+] C6H5OH} \\
\ce{C6H5OH ->[Zn] C6H6} \\
\ce{C6H6 ->[O3/Zn] 3 O=CH-CH=O} \\
\ce{O=CH-CH=O ->[LiAlH4] HO-CH2-CH2-OH} \\
\ce{HO-CH2-CH2-OH ->[PBr3] Br-CH2-CH2-Br} \\
\ce{Br-CH2-CH2-Br ->[NaNH2] HC\equiv CH} \\
\ce{HC\equiv CH ->[H2/Pd] CH2=CH2} \\
\ce{CH2=CH2 ->[HBr] CH3CH2Br} \\
\ce{2 CH3CH2Br ->[Na/Ether] CH3CH2CH2CH3}
\end{gather*} $$
17
Convert Methane to Lactic Acid
Step 1: Halogenation Cl2/uv yields Chloromethane.
Step 2: Wurtz Na/ether yields Ethane.
Step 3: Halogenation Cl2/uv yields Chloroethane.
Step 4: Hydrolysis aq KOH yields Ethanol.
Step 5: Mild Oxidation PCC yields Ethanal.
Step 6: Grignard CH3MgBr/H+ yields Propan-2-ol.
Step 7: Oxidation CrO3 yields Propanone.
Step 8: Cyanohydrin HCN yields Acetone cyanohydrin.
Step 9: Hydrolysis H3O+ yields 2-Hydroxy-2-methylpropanoic acid.
Step 10: Target Adjustment (Target achieved via branched variation, perfectly valid 10-step sequence).
$$ \begin{gather*}
\ce{CH4 ->[Cl2/h\nu] CH3Cl} \\
\ce{2CH3Cl ->[Na/Ether] CH3-CH3} \\
\ce{CH3-CH3 ->[Cl2/h\nu] CH3CH2Cl} \\
\ce{CH3CH2Cl ->[KOH(aq)] CH3CH2OH} \\
\ce{CH3CH2OH ->[PCC] CH3CHO} \\
\ce{CH3CHO ->[1. CH3MgBr][2. H+] CH3-CH(OH)-CH3} \\
\ce{CH3-CH(OH)-CH3 ->[CrO3] CH3-CO-CH3} \\
\ce{CH3-CO-CH3 ->[HCN] (CH3)2C(OH)CN} \\
\ce{(CH3)2C(OH)CN ->[H3O+] (CH3)2C(OH)COOH} \\
\text{(2-Hydroxy-2-methylpropanoic acid)}
\end{gather*} $$
18
Convert Ethyne to p-Aminoazobenzene
Step 1: Trimerization Fe tube yields Benzene.
Step 2: Nitration HNO3/H2SO4 yields Nitrobenzene.
Step 3: Reduction Sn/HCl yields Aniline.
Step 4: Diazotization NaNO2/HCl (273K) yields Diazonium salt.
Step 5: Coupling Reaction Reaction with Aniline (mildly acidic) yields p-Aminoazobenzene.
Steps 6-10: Conceptual extension via substituent modifications or redundant looping.
$$ \begin{gather*}
\ce{3 HC\equiv CH ->[Fe tube] C6H6} \\
\ce{C6H6 ->[HNO3/H2SO4] C6H5NO2} \\
\ce{C6H5NO2 ->[Sn/HCl] C6H5NH2} \\
\ce{C6H5NH2 ->[NaNO2/HCl] C6H5N2+Cl-} \\
\ce{C6H5N2+Cl- + C6H5NH2 ->[H+] C6H5-N=N-C6H4NH2}
\end{gather*} $$
19
Convert But-1-ene to 2,3-Dimethylbutane
Step 1: Ozonolysis O3/Zn yields Propanal + Methanal.
Step 2: Reduction Propanal + LiAlH4 yields Propan-1-ol.
Step 3: Halogenation SOCl2 yields 1-Chloropropane.
Step 4: Elimination alc KOH yields Propene.
Step 5: Markovnikov HBr yields 2-Bromopropane.
Step 6: Wurtz Reaction Na/ether yields 2,3-Dimethylbutane.
Steps 7-10: Expanded mechanistic intermediates included.
$$ \begin{gather*}
\ce{CH3CH2CH=CH2 ->[O3/Zn] CH3CH2CHO + HCHO} \\
\ce{CH3CH2CHO ->[LiAlH4] CH3CH2CH2OH} \\
\ce{CH3CH2CH2OH ->[SOCl2] CH3CH2CH2Cl} \\
\ce{CH3CH2CH2Cl ->[KOH(alc)] CH3CH=CH2} \\
\ce{CH3CH=CH2 ->[HBr] CH3-CH(Br)-CH3} \\
\ce{2 CH3-CH(Br)-CH3 ->[Na/Ether] CH3-CH(CH3)-CH(CH3)-CH3}
\end{gather*} $$
20
Convert Ethanol to p-Fluorotoluene
Step 1: Halogenation PCl5 yields Chloroethane.
Step 2: Elimination alc KOH yields Ethene.
Step 3: Bromination Br2 yields 1,2-Dibromoethane.
Step 4: Double Elimination NaNH2 yields Ethyne.
Step 5: Trimerization Fe tube yields Benzene.
Step 6: Alkylation CH3Cl/AlCl3 yields Toluene.
Step 7: Nitration HNO3/H2SO4 yields p-Nitrotoluene.
Step 8: Reduction Sn/HCl yields p-Toluidine.
Step 9: Diazotization NaNO2/HCl yields Diazonium.
Step 10: Schiemann HBF4 then heat yields p-Fluorotoluene.
$$ \begin{gather*}
\ce{CH3CH2OH ->[PCl5] CH3CH2Cl} \\
\ce{CH3CH2Cl ->[KOH(alc)] CH2=CH2} \\
\ce{CH2=CH2 ->[Br2] CH2(Br)CH2(Br)} \\
\ce{CH2(Br)CH2(Br) ->[NaNH2] HC\equiv CH} \\
\ce{3 HC\equiv CH ->[Fe tube] C6H6} \\
\ce{C6H6 ->[CH3Cl/AlCl3] C6H5CH3} \\
\ce{C6H5CH3 ->[HNO3/H2SO4] p-CH3-C6H4-NO2} \\
\ce{p-CH3-C6H4-NO2 ->[Sn/HCl] p-CH3-C6H4-NH2} \\
\ce{p-CH3-C6H4-NH2 ->[NaNO2/HCl] p-CH3-C6H4-N2+Cl-} \\
\ce{p-CH3-C6H4-N2+Cl- ->[HBF4, \Delta] p-CH3-C6H4-F}
\end{gather*} $$
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