Synthetic routes

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Athena Blair
Flashcards by Athena Blair, updated more than 1 year ago
Athena Blair
Created by Athena Blair over 3 years ago
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Synthetic routes (# means edit) Aliphatic (Write about the reaction in detail later)
Alkanes can be converted to: Halogenoalkane Short chain Alkenes and Alkanes (Cracking) Branched and Cyclic alkanes (Reforming) Combustion
Alkanes to Alkenes Cracking: Conversion of large hydrocarbons to smaller molecules by breakage of C-C bonds High Mr Alkanes = smaller Mr Alkanes+ Alkenes + (hydrogen)
Alkanes to Halogenoalkanes Reagent: Bromine/Chlorine Conditions: UV light Type of reaction: Free radical Substitution
Alkanes (Reforming)
Alkanes (Combustion)
Alkenes can be converted to: Alkane Alcohol Diol Halogenoalkane Dihalogenoalkane Polyalkane
Alkene to Alkane Reagent: Hydrogen Conditions: Nickel Catalyst Type of reaction: Addition/Reduction
Alkene to Alcohol (Hydration) High temperature 300 to 600°C High pressure 70 atm Catalyst of concentrated H3PO4 CH2=CH2 (g) + H2O (g) ---> CH3CH2OH (l)
Alkene to Diol Reagent: KMnO4 in an acidified solution Conditions: Room temperature Type of reaction: Oxidation Observation: purple colour of MnO4- ion will decolourise to colourless
Alkene to Halogenoalkane Reagent: HCl or HBr Conditions: Room temperature Mechanism: Electrophilic Addition Type of reagent: Electrophile, H+ Type of Bond Fission: Heterolytic
Alkene to Dihalogenoalkane Reagent: Bromine (dissolved in organic solvent) Conditions: Room temperature (not in UV light) Mechanism: Electrophilic Addition Type of reagent: Electrophile, Br+ Type of Bond Fission: Heterolytic
Alkene to Polyalkene -High pressure -Catalyst -Addition Polymerization
Dihalogenoalkane can be converted to: Diol Reagent: potassium (or sodium) hydroxide Conditions: In aqueous solution; Heat under reflux Mechanism: Nucleophilic Substitution Role of reagent: Nucleophile, OH-
Halogenoalkane can be converted to: Alcohol Amine Nitrile Alkenes
Halogenoalkane to Alcohol Reagent: potassium (or sodium) hydroxide Conditions: In aqueous solution; Heat under reflux Mechanism: Nucleophilic Substitution Role of reagent: Nucleophile, OH-
Halogenoalkane to Alkene Reagents: Potassium (or sodium) hydroxide Conditions: In ethanol ; Heat Mechanism: Elimination Role of reagent: Base, OH-
Halogenoalkane to Amine Reagent: NH3 dissolved in ethanol Conditions: Heating under pressure in a sealed tube Mechanism: Nucleophilic Substitution Type of reagent: Nucleophile, :NH3
Halogenoalkane to Nitrile -Ethanol and CN− -Nucleophilic substitution #####
Alcohol can be converted to: Carbonyls and Carboxylic acids Halogenoalkane Alkene Ester Combustion
Alcohol to Carbonyls Reaction: primary alcohol -> aldehyde Reagent: potassium dichromate (VI) solution and dilute sulphuric acid. Conditions: (use a limited amount of dichromate) warm gently and distil out the aldehyde as it forms Reaction: secondary alcohol -> ketone Reagent: potassium dichromate(VI) solution and dilute sulphuric acid. Conditions: heat under reflux
Alcohol to Halogenoalkane ### -PCl5, NaBr/H2SO4 , P+I2 -Heat under Reflux -Substitution
Alcohol to Carboxylic Acids Reagent: potassium dichromate(VI) solution and dilutesulphuric acid Conditions: use an excess of dichromate, and heat under reflux: (distill off product after the reaction has finished)
Alcohol to Alkene Reagents: Concentrated Phosphoric acid Conditions: warm (under reflux) Role of reagent: dehydrating agent/catalyst Type of reaction: acid catalysed elimination
Alcohol to Ester Reagent: Carboxylic acid Acid Catalyst: H2SO4 Condition- Heat under reflux Type of reaction -Esterification
Alcohol (Combustion) Alcohols combust with a clean flame CH3CH2OH + 3O2 -> 2CO2 + 3H2O
Carbonyls (Aldehydes and Ketones) can be converted to Alcohol Hydroxynitrile Aldehyde only can be converted to Carboxylic acid
Carbonyls to Alcohol Reagents: LiAlH4 In dry ether Conditions: Room temp. and pressure Type of reaction: Reduction Role of reagent: Reducing agent Aldehydes will be reduced to primary alcohols. Ketones will be reduced to secondary alcohols
Carbonyls to Hydroxynitrile Reaction: carbonyl  hydroxynitrile Reagent: HCN in presence of KCN Conditions: Room temperature and pressure Mechanism: nucleophilic addition
Aldehyde to Carboxylic acid Reagent: potassium dichromate (VI) solution and dilute sulphuric acid. Conditions: heat under reflux Observation: the orange dichromate ion ([Cr2O7]2-) reduces to the green Cr 3+ ion
Carboxylic acid can be converted to Alcohol Acyl chloride Ester Salt and inorganic products Aldehydes and then primary alcohols###
Carboxylic acid to Alcohol Reagents: LiAlH4 In dry ether Conditions: Room temperature and pressure Type of reaction: Reduction Role of reagent: Reducing agent
Carboxylic acid to Acyl Chloride Reagent: PCl5 phosphorous(v)chloride Conditions: room temp
Carboxylic acid to Salt and inorganic products Salt formation reactions of carboxylic acids =>acid + metal (Na) -> salt + hydrogen =>acid + alkali (NaOH) -> salt + water =>acid + carbonate (Na2CO3) --> salt + water + CO2
Carboxylic acid to Ester Reagent: Alcohol Acid Catalyst: H2SO4 Condition- Heat under reflux Type of reaction -Esterification
Acyl Chloride can be converted to Carboxylic acid Carboxylate salt### Ester Primary Amide Secondary Amide
Acyl Chloride to Carboxylic acid Reagent: water Conditions: room temp.
Acyl Chloride to Ester Reagent: alcohol Conditions: room temp.
Acyl Chloride to Primary Amide Reagent: ammonia Conditions: room temp.
Acyl Chloride to Secondary Amide Reagent: primary amine Conditions: room temp.
Amine can be converted to Secondary Amine, Tertiary Amine Salt Secondary Amide
Amines to Salt Amines as bases react with acids to form ammonium salts. CH3NH2 (aq) +HCl (aq) -> CH3NH3 +Cl- (aq) {Methylamine} {methylammonium chloride} 2CH3NH2 (aq) +H2SO4 (aq) -->(CH3NH3+)2SO42- (aq)
Amine to Secondary Amine/Tertiary Amine ### -Haloalkane -Nucleophilic substitution
Amine to Secondary Amide Change in functional group: acyl chloride  secondary amide Reagent: primary amine*** Conditions: room temp. Forming Amides: Aliphatic amines and phenylamine can react with acyl chlorides to form amides in a **nucleophilic addition- elimination reaction**
Nitrile can be converted to Amine Carboxylic acid Carboxylate salt##
Nitrile to Carboxylate Salt ### ....
Nitrile to Amine
Nitrile to Carboxylic acid -Acid Hydrolysis Reagent: dilute hydrochloric/ sulphuric acid. Conditions: heat under reflux CH3CH2CN + H+ + 2H2O -> CH3CH2COOH + NH4+
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