organic synthesis (aliphatic compounds) alkene alkane ketone alcoholhalogenoalkaneamine...
TRANSCRIPT
![Page 1: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/1.jpg)
Organic Synthesis (aliphatic compounds)
ALKENE ALKANE
KETONE ALCOHOL HALOGENOALKANE AMINE
2-HYDROXYNITRILE(CYANOHYDRIN)
ALDEHYDE NITRILE AMIDE
CARBOXYLICACID ESTER
ACYLCHLORIDE
![Page 2: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/2.jpg)
ALKENE → ALCOHOL
• COLD CONC. SULFURIC ACID
• THEN ADD WATER
• Electrophilic addition (hydration)
![Page 3: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/3.jpg)
ALCOHOL → ALKENE
• CONC SULFURIC ACID• Heat under reflux
• OR
• Al2O3 • 300 °C
• Elimination (dehydration)
![Page 4: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/4.jpg)
ALKENE → ALKANE
• HYDROGEN
• Heat
• Nickel catalyst
• Addition (hydrogenation)
![Page 5: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/5.jpg)
ALKENE → HALOGENOALKANE
• HYDROGEN HALIDE, e.g. HBr
• Room temperature
• Electrophilic addition
![Page 6: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/6.jpg)
HALOGENOALKANE→ ALKENE
• POTASSIUM HYDROXIDE (ethanolic)
• Elimination
![Page 7: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/7.jpg)
HALOGENOALKANE→ ALCOHOL
• POTASSIUM HYDROXIDE (aqueous)
• Heat under reflux
• Nucleophilic Substitution
![Page 8: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/8.jpg)
HALOGENOALKANE→ AMINE
• CONC. AMMONIA (aqueous)
• Heat
• Nucleophilic Substitution
![Page 9: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/9.jpg)
HALOGENOALKANE→ NITRILE
• POTASSIUM CYANIDE• ETHANOL (SOLVENT)
Or
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• Then add water
• Nucleophilic Substitution
![Page 10: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/10.jpg)
KETONE → ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• Then add water OR
• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER (SOLVENT)
• Reduction
• ALSO GRIGNARD REAGENTS
![Page 11: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/11.jpg)
SECONDARY ALCOHOL → KETONE
• POTASSIUM DICHROMATE (VI)
• DILUTE SULFURIC ACID (to acidify)
• Heat under reflux
• Oxidation
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ALDEHYDE → CARBOXYLIC ACID
• POTASSIUM DICHROMATE (VI)
• CONCENTRATED SULFURIC ACID (to acidify)
• Heat under reflux
• Oxidation
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PRIMARY ALCOHOL → ALDEHYDE
• POTASSIUM DICHROMATE (VI)
• DILUTE SULFURIC ACID (to acidify)
• Distillation
• Oxidation
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PRIMARY ALCOHOL → CARBOXYLIC ACID
• POTASSIUM DICHROMATE (VI) Excess
• SULFURIC ACID Concentrated
• Heat under reflux
• Oxidation
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KETONE → 2-HYDROXYNITRILE
• POTASSIUM CYANIDE
• DILUTE SULFURIC ACID
- React to produce hydrogen cyanide
• Nucleophilic Addition
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ALDEHYDE → 2-HYDROXYNITRILE
• POTASSIUM CYANIDE
• DILUTE SULFURIC ACID
- React to produce hydrogen cyanide
• Nucleophilic Addition
![Page 17: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/17.jpg)
ALDEHYDE → PRIMARY ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)
Or
• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
• ALSO GRIGNARD REAGENTS
![Page 18: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/18.jpg)
CARBOXYLIC ACID → ALDEHYDE
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)
Or
• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
![Page 19: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/19.jpg)
CARBOXYLIC ACID → PRIMARY ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT) Or
• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
![Page 20: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/20.jpg)
NITRILE → AMINE
• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• THEN ADD WATER Or
• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
![Page 21: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/21.jpg)
NITRILE → CARBOXYLIC ACID
• DILUTE HYDROCHLORIC ACID• Heat under reflux • Hydrolysis
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CARBOXYLIC ACID → ESTER
• ALCOHOL
• CONC. SULFURIC ACID (catalyst)
• Condensation Reaction
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ALCOHOL→ ESTER
• CARBOXYLIC ACID
• CONC. SULFURIC ACID (catalyst)
• Condensation Reaction
![Page 24: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/24.jpg)
ALKANE→ HALOGENO ALKANE
• HALOGEN
• UV light
• Free Radical Substitution
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CARBOXYLIC ACID → ACYL CHLORIDE
• SCl2O (or PCl3, PCl5)
• Heat under reflux
• Nucleophilic substitution reaction
![Page 26: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/26.jpg)
HALOGENOALKANE → ALCOHOL
• KOH or NaOH (aqueous)
• Heat under reflux
• Nucleophilic substitution– SN2 for 1° and 2° halogenoalkanes
– SN1 for 3° halogenoalkanes
![Page 27: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/27.jpg)
ALCOHOL → HALOGENOALKANE
• SODIUM HALIDE (solid) e.g. NaBr
OR
• PHOSPOROUS HALIDE e.g. PCl3
• CONC. SULPHURIC ACID (catalyst)• Reflux
• Nucleophilic substitution reaction
![Page 28: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/28.jpg)
ACYL CHLORIDE → ESTER
• ALCOHOL
• Condensation reaction
![Page 29: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/29.jpg)
AMIDE → AMINE
• LiAlH4
• Reduction
![Page 30: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC](https://reader035.vdocuments.us/reader035/viewer/2022062221/56649da95503460f94a974e5/html5/thumbnails/30.jpg)
AMIDE → NITRILE
• P2O5
• Distillation
• Elimination