Organic Reactions

All of the organic reactions needed for CH4

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  • Created by: Zoe Fox
  • Created on: 23-11-13 16:32

Alcohols and Phenol

  • Primary Alcohol >>> Carboxylic Acid

Conditions: Reflux with acidified potassium dichromate

Observations: Colour Change (Orange >>> Green)

  • Primary Alcohols >>> Alkenes

Dehydration/Elimination Reaction

Conditions: Pass ethanol vapour over heated aluminium oxide

  • Secondary Alcohols >>> Secondary Halogenalkanes (Lucas Test)

React secondary alcohol with hydrogen halide to form secondary halogenoalkane.

Conditions: Alcohol treated with anhydrous zinc chloride and conc. HCL

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Alcohols and Phenol Pt.2

  • Alcohol >>> Ester

React alcohol with carboxylic acid

Conditions: Reflux with conc. H2SO4

  • Alcohol >>> Acyl Chlorides

Forms an ester and HCL

  • Primary alcohol >>> Aldehydes + Carboxylic Acids

Oxidation

Aldehyde Conditions: Warm with acidified potassium dichromate, product must be distilled off as it forms.

Observations: Colour Change (Orange >>> Green)

Carboxylic Acid Conditions: Reflux

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Alcohols and Phenol Pt.3

  • Secondary Alcohols >>> Ketones

Oxidation

Conditions: Reflux with acidified potassium dichromate

Observations: Colour Change (Orange >>> Green)

  • Phenol >>> 2,4,6 - Tribromophenol

Electrophillic Substitution

Conditions: React with 3HBr

Observations: Bromine water decolourises - white ppt forms with antiseptic smell

  • Phenol >>> Sodium Phenoxide

Conditions: Reacts with aqueous sodium hydroxide

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Carbonyl Compounds

  • Aldehyde >>> Primary Alcohols

Reduction

Conditions: Aqueous sodium tetrahydridoborate (NaBH4)

  • Ketone >>> Secondary Alcohol

Reduction

Conditions: Same as above

  • Carbonyl Compound >>> Hydroxynitrile

Nucleophillic Addition >>> IT ADDS AN EXTRA CARBON!!!!!!! (V.IMPORTANT!!!)

Conditions: React with HCN/KCN

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Carboxylic Acids

  • Carboxylic Acid >>> Acyl Chloride (Acylation)

The product is separated by distillation

Conditions: React with phosphorus (V) chloride (PCl5)

  • Carboxylic Acid >>> Primary Alcohol

Reduction

Conditions: Reducing agent: Lithium tetrahydrido aluminate (LiAlH4) in DRY ETHER!!

  • Carboxylic Acid >>> Alkane

Decarboxylation >>> REMOVES A CARBON ATOM!!!!!! (V.IMPORTANT!!!)

Conditions: Usually carried out with the carboxylate salt, it's mixed with SODA LIME (NaOH + CaO2)

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Carboxylic Acids Pt.2

  • Carboxylic Acid >>> Amides

Dehydration

Conditions:

Step 1: Excess carboxylic acid is refluxed with ammonium carbonate to form the ammonium salt (excess prevents the ammonium salt from decomposing into the carboxylic acid and ammonia).

Step 2: On heating, the ammonium salt of the acid dehydrates forming the amide.

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Carboxylic Acid Derivatives

  • Amides >>> Nitriles

Dehydration

Conditions: Strongly heat amide with phosphorus (V) oxide (P4O10-)

  • Amides >>> Carboxylate Salt and Ammonia

Conditions: Heat with aqueous strong alkalis (NaOH)

  • Nitrile >>> Carboxylate Salt and Ammonia

Hydrolysis

Conditions: Heat with aqueous strong acids (H2SO4)

  • Nitrile >>> Carboxylate Salt and Ammonia Gas

Hydrolysis

Conditions: Heat with aqueous strong alkalis (NaOH)

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Carboxylic Acid Derivatives Pt.2

  • Nitriles >>> Amines

Reduction

Conditions: React with lithium tetrahydrido aluminate (LiAlH4) in DRY ETHER!!!

  • Primary Amines >>> Substituted Amides

Conditions: React with ethanoyl chloride

  • Aliphatic Amine >>> Alcohol, Nitrogen Gas and Water

Conditions: React at room temperature using nitric acid (HNO2) prepared insitu from sodium nitrate (III) and hydrochloric acid

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Benzene

  • Halogenation of Benzene

Electrophillic Substitution

Conditions: React at room temperature in anhydrous conditions using a halogen carrier catalyst such as aluminium chloride (AlCl3)

  • Nitration of Benzene

Electrophillic Substitution

Conditions: Reflux at 50°C or below with a mixture of conc. HNO3 and conc. H2SO4.

  • Nitrobenzene >>> Phenylamine

Reduction

Conditions: Heat with Tin (Sn) and conc. HCL, then add NaOH to release the phenylamine. The mixture is separted by steam distillation and purified by solvent extraction with epoxyethene

     

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Hydrocarbons and Halogenoalkanes

  • CH4 Free Radical

Photochlorination

 

  • Alkene >>> Alkane

Catalytic Hydrogenation

Conditions: Nickel catalyst

  • Bromoethane >>> Ethene

Elimination of HBr

Conditions: NaOH/Ethanol and Reflux/Heat 

  • Halogenoalkane >>> Alcohol

Hydrolysis/ Nucleophillic Substitution

Conditions: Warm with aqueous NaOH

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Hydrocarbons and Halogenoalkanes Pt.2

  • Ethene >>> Ethanol

Industrial Preparation

Conditions: Steam and ethene are passed over a catalyst of phosphoric acid (H3PO4) at a temperature of 300°C and at 60 – 70 atm pressure.

  • Halogenoalkane >>> Amine

Nucleophillic Substitution

Conditions: Heat with ethanolic ammonia in sealed tube immersed in boiling water

  • Halogenoalkanes >>> Nitriles

Nucleophillic Substitution

Conditions: Heat with ethanolic KCN

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