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A-level Chemistry: 3.3.14 Organic Synthesis

Chemistry31 CardsCreated 2 months ago

This flashcard set outlines the key reactions of halogenoalkanes, including free-radical substitution to form halogenalkanes, and nucleophilic substitution pathways leading to amines, nitriles, and alcohols. It highlights the reagents, conditions, and product types depending on the class of halogenoalkane.

Alkane → Halogenalkane

State the reaction and the conditions

  • Free-radical substitution

  • X2, UV light

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Key Terms

Term
Definition

Alkane → Halogenalkane

State the reaction and the conditions

  • Free-radical substitution

  • X2, UV light

Halogenalkane → Secondary/tertiary amines, their salts and quaternary ammonium salts

State the reaction and the conditions

  • Nucleophilic substitution

  • Ammonia, heat

  • (not primary halogenalkanes)

Halogenalkane → Primary Amine

State the reaction and the conditions

  • Nucleophilic substitution

  • Excess ammonia, heat

  • (primary halogenalkanes only)

Halogenalkane → Nitrile

State the reaction and the conditions

  • Nucleophilic substitution

  • KCN(aq), ethanol, reflux

Halogenalkane → Alcohol

State the reaction and the conditions

  • Nucleophilic substitution

  • Warm, NaOH(aq), reflux

Halogenalkane → Alkene

State the reaction and the conditions

  • Elimination

  • KOH, ethanol, reflux

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TermDefinition

Alkane → Halogenalkane

State the reaction and the conditions

  • Free-radical substitution

  • X2, UV light

Halogenalkane → Secondary/tertiary amines, their salts and quaternary ammonium salts

State the reaction and the conditions

  • Nucleophilic substitution

  • Ammonia, heat

  • (not primary halogenalkanes)

Halogenalkane → Primary Amine

State the reaction and the conditions

  • Nucleophilic substitution

  • Excess ammonia, heat

  • (primary halogenalkanes only)

Halogenalkane → Nitrile

State the reaction and the conditions

  • Nucleophilic substitution

  • KCN(aq), ethanol, reflux

Halogenalkane → Alcohol

State the reaction and the conditions

  • Nucleophilic substitution

  • Warm, NaOH(aq), reflux

Halogenalkane → Alkene

State the reaction and the conditions

  • Elimination

  • KOH, ethanol, reflux

Nitrile → Primary Amine

State the reaction and the conditions

  • Reduction

  • LiAlH4, dry ether, dilute H2SO4

  • OR hydrogen gas, platinum/nickel catalyst, high temperature and pressure

Alkene → Halogenalkane

State the reaction and the conditions

  • Electrophilic Addition

  • HX, 20°C

Alkene → Dibromoalkane

State the reaction and the conditions

  • Electrophilic addition

  • Br2, 20°C

  • (test for unsaturation)

Alkene → Alcohol

State the reaction and the conditions

  • Hydrolysis

    • H3PO4 catalyst, steam, 300°C, 60 atm

  • Electrophilic addition

    • H2O, H2SO4 catalyst


Alcohol → Alkene

State the reaction and the conditions

  • Elimination

  • conc H2SO4, reflux

Alcohol → Carboxylic Acid

State the reaction and the conditions


  • Oxidation

  • K2Cr2O7, H2SO4, relfux

  • (primary alcohols only)


Alcohol → Aldehyde/ketone

State the reaction and the conditions

  • Oxidation

  • K2Cr2O7, H2SO4, heat in distillation apparatus


Aldehyde/ketone → Alcohol

State the reaction and the conditions

  • Reduction/nucleophilic addition

  • NaBH4 in water with methanol

Aldehyde/ketone → Hydroxynitrile

State the reaction and the conditions

  • Nucleophilic addition

  • KCN(aq), H2SO4, 20°C

Carboxylic Acid → Ester

State the reaction and the conditions

  • Esterification

  • alcohol, conc. H2SO4 catalyst, heat

Ester → Carboxylic Acid

State the reaction and the conditions

  • Hydrolysis

  • dilute H2SO4 catalyst, H2O, reflux

  • OR dilute NaOH(aq), reflux

Acyl Chloride / Acid Anhydride → Carboxylic Acid

State the reaction and the conditions

  • Nucleophilic Addition-Elimination

  • H2O, 20°C

Acyl Chloride / Acid Anhydride → Ester

State the reaction and the conditions

  • Nucleophilic Addition-Elimination

  • Alcohol, 20°C

Acyl Chloride / Acid Anhydride → Primary Amine

State the reaction and the conditions

  • Nucleophilic Addition-Elimination

  • NH3, 20°C

Acyl Chloride / Acid Anhydride → N-Substituted Amide

State the reaction and the conditions

  • Nucleophilic Addition-Elimination

  • Amine, 20°C

State how chemists design synthesis routes to be safe

Chemists try designing routes that use non-hazardous starting materials to limit the potential for accidents and environmental damage

State how chemists design synthesis routes to be less wasteful

  • Use processes with high atom economies and high percentages yields

  • Waste can be reduced by designing synthesis routes that have as few steps as possible

Why are processes with high atom economies and high percentages yields preferred?

∵ they convert more of starting material into useful products

Give an example of how you can reduce both hazards associated with process and amount of waste created by a synthesis route

Avoiding solvents

Explain how avoiding solvents reduces hazards

Solvents are often flammable and toxic so pose safety risks

Explain how avoiding solvents reduces waste

If solvent has to be disposed after reaction is complete = lots of waste