30 Most Important Organic Conversions PDF

# 30 Most Important Organic Conversions ## How can you convert the following? But-1-ene to 1-iodobutane * $CH_3-CH_2-CH=CH_2 + HBr$ (peroxide) * $CH_3-CH_2-CH_2-CH_2 + NaI$ (acetone) ## How do you convert: Propene to 1-iodopropane? * $CH_3-CH=CH_2 + HBr$ (peroxide) * $CH_3-CH_2-CH_2 + NaI$ (...

# 30 Most Important Organic Conversions ## How can you convert the following? But-1-ene to 1-iodobutane * $CH_3-CH_2-CH=CH_2 + HBr$ (peroxide) * $CH_3-CH_2-CH_2-CH_2 + NaI$ (acetone) ## How do you convert: Propene to 1-iodopropane? * $CH_3-CH=CH_2 + HBr$ (peroxide) * $CH_3-CH_2-CH_2 + NaI$ (acetone) ## Write chemical equations when: * **(A) Methyl chloride is treated with AgNO2.** * $CH_3-Cl + AgNO_2 \longrightarrow CH_3-NO_2 + AgCl$ * **(B) Bromobenzene is treated with CH3Cl in the presence of anhydrous AICI3.** * * $Br$ * * $CH_3$ * * * $Br$ * * $CH_3$ * * + * * $CH_3$ * * (minor) ## Write chemical equation when: * **(A) ethyl chloride is treated with aqueous KOH** * $CH_3-CH_2-Cl + KOH(aq) \longrightarrow CH_3-CH_2-OH + KCl$ * **(B) chlorobenzene is treated with CH3COCI in presence of anhydrous AICI3.** * * $O$ * * $ + CH_3COCl$ * * $O$ * * $COCl_3 +$ * * $O$ * * $COCH_3$ ## What happens when: * **(A) anisole is treated with CH3Cl/anhydrous AICI3?** * * $OCH_3$ * * $+CH_3Cl$ * * $OCH_3$ * * $CH_3$ * **(B) phenol is oxidised with Na2Cr2O7?** * * $OH$ * * $Na_2Cr_2O_7$ * * $Benzoquinone$ * **(C) (CH3)3C-OH is heated with Cu/573K?** * * $CH_3$ * * $CH_3-C-OH$ * * $CH_3$ * * $Cu$ * * $573K$ * * $CH_3$ * * $CH-C=CH_2$ * * $CH_3$ ## Carry out the following conversion: Phenol to salicylaldehyde: * **(A)** * * $OH$ * * $i) NaOH, CHCl_3$ * * $ii) H_2O$ * * $CHO$ * * $Salicylaldehyde$ * or * $o-Hydroxybenzaldehyde$ * * $Reimer$ * $Tiemann Reaction$ ## Carry out the following conversion: Propene to Propanol: * **(B)** * * $H^{+} OH$ * * $CH_3-CH=CH_2$ * $i) B_2H_6$ * $ii) H_2O_2, OH^-$ * $CH_3-CH_2-CH_2-OH$ * $Propan-1-ol$ * $Hydroboration$ * $Oxidation$ ## Predict the reagent for carrying out the following conversion: Phenol to benzoquinone: * $OH$ * * $Na_2Cr_2O_7$ ## Predict the reagent for carrying out the following conversion: Phenol to 2, 4, 6-tribromophenol: * $OH$ * * $+3Br_2, H_2O$ * $3(Br-Br)$ * * $Br$ * * $Br$ * * $+ 3HBr$ * * $2,4,6-Tribromophenol$ * $(White ppt)$ ## How are the following conversions carried out?: * **(A) Propene to propan - 2 - ol:** * $CH_3-CH=CH_2 + H_2O$ * $H^{+}$ * $CH_3-CH-CH_3$ * $OH$ * $Acid$ * $Catalysed$ * $Hydration$ * **(B) Benzyl chloride to benzyl alcohol:** * $CH_2Cl$ * * $O$ * * $+ NaOH(aq)$ * * $CH_2OH $ ## How would you carry out the following conversion?: * **(A) Benzyl chloride to benzyl alcohol:** * * $C=O + C_6H_5-MgCl$ * * $H$ * * $H-C-OH$ * * * $CH_2$ * * $MgCl + H_2O \longrightarrow$ * * $CH_2-OH $ * **(B) Ethyl magnesium chloride to propan-1-ol:** * $CH_3-CH_2-CH_2-OH$ * $1^o \ alcohol$ * $R-C=O + RMgX$ * $2^o\ alcohol$ * $R-=O + RMgX \longrightarrow 3^o \ alcohol$ * $CH_3 + Mg-OH$ ## How do you convert the following?: * **(A) Phenol to anisole:** * * $OH$ * * $+ NaOh \longrightarrow$ * * $+ CH_3$ * * $Sod. Phenol$ * * * $CH_3$ * * $CH_3CH-OH + PCC \longrightarrow$ * * $CH_3$ * * $CH_3-CH_2-MgCl \longrightarrow$ * * $CH_3$ * * $C=O$ * * $CH_3$ * * $CH_3$ * * $↑ H_3O^+$ * * $CH_3$ * * * $CH_3$ * **(B) Propan-2-ol to 2-methylpropan-2-ol:** * * $O$ * * $CH_3-C=O + CH_3-C=O $ * * $H$ * * $H$ * * $NaOh \longrightarrow$ * * $CH_3-C=CH-C=O$ * * $H$ * * $H$ * * $Williamson's $ * $Synthesis$ ## How do you convert the following?: * **(A) Phenol to anisole:** * $NH_2$ * * $+ HONO + HCl$ * * * $N_2^+$ * * $+H_2O \longrightarrow$ * * $+H-OH \longrightarrow $ * * $OH$ * * $Phenol$ * * $Diazotization \ Reaction$ * **(B) Propan-2-ol to 2-methylpropan-2-ol:** (Same as above) * **(C) Aniline to phenol:** (Same as above) ## Write the equations involved in the acetylation of salicylic acid. * $OH$ * * $COOH$ * * $1) NaOH, (O_2$ * * $ii) H_2O$ * * $ + CH_3-C-CH_3 $ * * $ Salicylic Acid$ * * $ CH_3$ * * $ O-CH_3$ * * $COOH$ * * $ + CH_3COOH$ * * $Aspirin$ * * $OH$ ## How are the following conversions carried out? * **(A) Propene to Propan - 2 - ol:** * $1^o \ alcohol \longrightarrow PCC \longrightarrow Aldehyde$ * $2^o \ alcohol \longrightarrow PCC \longrightarrow Ketone$ * **(B) Ethyl chloride to Ethanal** * $CH_3-CH_2-Cl + KOH(aq) \longrightarrow CH_3-CH_2-OH \longrightarrow PCC \longrightarrow CH_3-CHO$ ## (A) Write the formula of reagents used in the following reactions. * **(i) Bromination of phenol to 2, 4, 6 – tribromphenol:** * $Br_2, H_2O$ * **(ii) Hyroboration of propene and then oxidation to propanol:** * $B_2H_6$ * $H_2O_2, OH^-$ ## How do you convert the following: Ethyne to ethanal: * $CH \equiv CH + H_2O$ * $dil. HgSO_4$ * $dil. H_2SO_4$ * $CH_3-CH$ * $OH$ * $HO \longrightarrow HO$ * $enol \longrightarrow Tautomerisation$ * $CH_3-CH$ * $ || O$ ## How can you convert the following: Acetone to pro-pene? * $ CH_3-C - CH_3 + H_2$ * * $O$ * $Ni$ * $CH_3-CH-CH_3$ * $H$ * $ \alpha \beta$ * $ \longrightarrow CH_3-CH-CH_2 $ * * $OH$ * $Δ$ * $ \longrightarrow CH_3-CH=CH_2$ ## Write chemical equations for the following reactions: * **(A) Propanone is treated with dilute BaOH2:** * $CH_3-C=O + CH_3-C=O \longrightarrow CH_3-C=CH-CO-CH_3 $ * * $O$ * $O$ * $dil$ * * $Ba(OH)_2$ * * $Aldol Condensation \ Reaction$ * **(B) Acetophenone is treated with Zn(Hg)/ conc.HCl** * $COCH_3$ * $ + Zn-Hg$ * $H_2O$ * $ \longrightarrow CH_3$ * * $CH_2-CH_3$ * * $Ethyl \ Benzene$ ## How do you convert the following: Ethanal to Propanone: * $CH_3-C=O$ * * $CH_3MgBr$ * * $H_3O^+$ * * $CH_3-C=O $ * * $CH_3$ * $ \longrightarrow Cu \longrightarrow 573k$ * $CH_3-C-CH_3$ * * $O $ # Convert the following: * **(A) Bromomethane to ethanoic acid.** * * $C-OH$ * * $NH_2$ * * $C-OH$ * * $CHO$ * * $PCC$ * **(B) Benzene to p-nitrobenzoic acid.** * * $COOH$ * * $NO_2$ * * $KMnO4/KOH$ * * $H_3O^+$ * **(C) Benzoic acid to benzaldehyde.** * $CH_3-Br + KCN \longrightarrow CH_3-CN + H_2O \longrightarrow CH_3-COOH $ * * $COOH$ * * $+CH_3Cl$ * * $Anhyd.$ * * $AlCl_3$ * * * $COOH$ * * $NO_2$ * * $+Conc. HNO_3 + H_2SO_4$ * * $H_2SO_4$ * * $COOH$ * * $Benzoic \ Acid \longrightarrow Benzaldehyde$ * * $ + SOCl_2 \longrightarrow C + H_2O$ * * $Pd-BaSO4$ * * $+ H_2$ * * $Poisoned \ by$ * $S$ * * * $CHO$ * * $Benzaldehyde$ # Convert the following: * **(A) Benzoic acid to Benzaldehyde:** * $COOH \longrightarrow$ * * $CHO$ * **(B) Propan-1-ol to 2-Bromopropanoic acid:** * $CH_3-CH_2-CH_2-OH \longrightarrow KMnO_4 \longrightarrow CH_3-CH_2-COOH + Br_2 \longrightarrow $ * * $RedP, CH_3-CH-COOH$ * * $Br$ * $Br$ * **(C) Acetaldehyde to But-2-enal:** * * $CH_3-C= O + CH_3-C=O $ * * $H$ * * $H$ * * $dil.$ * * $NaOh$ * * $ \longrightarrow CH_3-C=CH-C=O$ * * $H$ * * $H$ # How do you convert the following: Toluene to benzoic acid? * $CH_3$ * * $COOH$ * * $i) KMnO_4 - KOH$ * * $ii) H_3O^+$ # Do the following conversion in not more than two steps: * **Ethyl benzene to benzoic acid:** * $CH_2-CH_3$ * * $COOH$ * * $i) KMnO_4 - KOH$ * * $ii) H_3O^+$ # How will you convert the following in not more than two steps: * **(A) Acetophenone to benzoic acid:** * $C-CH_3$ * * $COOH$ * * $i) KMnO_4-KOH$ * * $ii) H_3O^+$ * * $Pot. Benzoate$ * * $Benzoic \ Acid$ * **(B) Ethanoic acid to 2-hydroxyethanoic acid:** * $CH_3-COOH + Br_2$ * $Red P, \longrightarrow CH_3-COO4 + KOH(aq) \longrightarrow CH_3-COOH$ * $Br$ * $ OH$ # Complete the following reaction: * $CH_3$ * * $CH_3-CH-COOH$ * * $CH_3$ * * $i) Br_2/Red P_4$ * * $ii) H_2O$ * * $CH_3$ * * $CH_3-C-COOH$ * * $Br$ * * $CH_3$ * * $CH_3-C-COOH$ * * $OH$ # Carry out the following conversions: * **Propanoic acid to Acetic acid:** * * $CH_3-CH_2-C-OH$ * * $NH_3$ * * $CH_3-CH_2-C-NH_2$ * * $O$ * * $CH_3-CH_2-C-NH_2 + HONO \longrightarrow CH_3-CH_2-OH KMnO_4 \longrightarrow CH_3-COOH $ * * $O$ * * $NH_2$ * * $CH_3-CH_2-NH_2 + HONO \longrightarrow CH_3-CH_2-OH KMnO_4 \longrightarrow CH_3-COOH $ * * $N_2$ * * $O$ # Convert the following: * **(A) Phenol to N-phenylethanamide.** * * $OH $ * * $Zn$ * * $Conc. HNO_3 + Conc. H_2SO_4 \longrightarrow NO_2$ * * $OH$ * * $CH_3-CH_2-Cl + NaOH(aq) \longrightarrow CH_3-CH_2-OH \longrightarrow KMnO_4 \longrightarrow$ * * $COOH$ * * $CH_3-COOH + NH_3 \longrightarrow CH_3-CO-NH_2 + Br_2 + 4KOH \longrightarrow $ * $CH_3-NH_2$ * **(B) Chloroethane to methanamine.** * $CH_3-CH_2-Cl + NaCN \longrightarrow CH_3-CN + H_2 \longrightarrow CH_3-CH_2-NH_2$. * * $LiAlH_4 \longrightarrow CH_3-NH_2$ * **(C) Propanenitrile to ethanol.** * $CH_3-CH_2-CN + 4[H] \longrightarrow CH_3-CH_2-CH_2-NH_2 $ * * $LiAlH_4 \longrightarrow CH_3-CH_2-CH_2-OH$ # What happens when: * **(A) N-ethylethanamine reacts with benzene-sulphonyl chloride.** * $CH_3-CH_2-N-CH_3 + C_6H_5-SO_2Cl \longrightarrow CH_3-CH_2-N-SO_2-C_6H_5$ * * $H $ * **(B) benzylchloride is treated with ammonia followed by the reaction with Chloromethane.** * $CH_2Cl \longrightarrow NH_3 \longrightarrow CH_2-NH_2$ * * $CH_2Cl \longrightarrow CH_2-N-CH_3$ * * $H $ # Write equations involved in the following reactions: * **(A) Ethanamine reacts with acetyl chloride.** * $CH_3-CH_2-NH_2 + CH_3-COCl \longrightarrow CH_3-CH_2-NH-CO-CH_3$ * **(B) Aniline reacts with bromine water at room temperature** * $C_6H_5-NH_2 + 3Br_2 \longrightarrow C_6H_5-NH_2$ * * $Br$ * * $Br$ * **(C) Aniline reacts with chloroform and ethanolic potassium hydroxide.** * $C_6H_5-NH_2 + CHCl_3 + 3KOH \longrightarrow $ * * $C_6H_5-NC + 3KCl +3H_2O$ * * $O$ # Carry out the following conversion: * **Bromomethane to ethanol.** * $CH_3-Br + KCN \longrightarrow CH_3-CN + [H] \longrightarrow CH_3-CH_2-NH_2 $. * $LiAlH_4 \longrightarrow CH_3-CH_2-OH$ # Carry out the following conversions : * **Benzoic acid to aniline** * * $COOH$ * * $NH_2$ * * $CH_3-Br + KCN \longrightarrow CH_3-CN \longrightarrow CH_3-CH_2-NH_2 $ * * $CH_3-CH_2-NH_2 + HNO_2 \longrightarrow CH_3-CH_2-OH KMnO_4 \longrightarrow CH_3-COOH$ * * $NO_2$ * * * $OH$ * * $+ Br_2 + 4KOH \longrightarrow$ * * $NH_2$ * * * $OH$ * * $ + Br_2 + 4KOH \longrightarrow$ * * $NH_2$ # How do you convert the following: * **ethanenitrile to ethanamine:** * $CH_3-C=N + 4[H]$ * * $LiAlH_4 \longrightarrow CH_3-CH_2-NH_2$ # How will you convert the following: Aniline to N-phenylethanamide. * * $NH_2$ * * $ + CH_3-C=O \longrightarrow NH-C-CH_3$ * * $O$ # How will you convert aniline into p-bromoaniline? Write relevant chemical equation. * $NH_2$ * * $+ Br_2$ * * $Pyridine$ * * $NH_2$ * * $ Br$ + * * $HBr \longrightarrow$ * * $NH_2 $ * * $Br$