AQA A level Chemistry 3.3.14: Organic synthesis

What mechanism is involved in converting an alkane to a halogenoalkane? (1)

Free Radical Substitution

What are the reagents and conditions for the reaction of an alkane to a halogenoalkane? (2)

- Reagents: Chlorine.

- Conditions: UV light

Provide the equation for the reaction of methane with chlorine to form a halogenoalkane. (1)

CH₄ + Cl₂ → CH₃Cl + HCl

What mechanism is used to convert a halogenoalkane to an alcohol? (1)

Nucleophilic Substitution

What are the reagents and conditions for the conversion of a halogenoalkane to an alcohol? (2)

- Reagents: NaOH

- Conditions: Warm aqueous

Write the general equation for the reaction of a halogenoalkane with NaOH to form an alcohol. (1)

R-Cl + NaOH → R-OH + NaCl

What is the mechanism and equation for the conversion of a halogenoalkane to an alkene? (3)

- Mechanism: Elimination

- Equation: CH₃CH₂Cl + KOH → CH₂=CH₂ + KCl + H₂O

- Conditions: Hot in ethanol

How can a halogenoalkane be converted to a nitrile? Include the mechanism, reagents, and equation. (4)

- Mechanism: Nucleophilic Substitution

- Reagents: KCN

- Equation: R-Cl + KCN → R-CN + KCl

- Conditions: Aqueous ethanol

How can a halogenoalkane be converted to a primary amine? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Substitution

- Reagents: Ammonia (Excess)

- Equation: R-Cl + 2NH₃ → R-NH₂ + NH₄Cl

How can an alkene be converted to an alkane? Include the reaction, reagents, conditions, and equation. (4)

- Reaction: Catalytic hydrogenation

- Reagents: Hydrogen

- Conditions: Ni catalyst

- Equation: CH₂=CH₂ + H₂ → CH₃CH₃

How can an alkene be converted to a dibromoalkane? Include the mechanism, reagents, and equation. (3)

- Mechanism: Electrophilic Addition

- Reagents: Bromine

- Equation: CH₂=CH₂ + Br₂ → CH₂BrCH₂Br

How can an alkene be converted to a bromoalkane? Include the mechanism, reagents, and equation. (3)

- Mechanism: Electrophilic Addition

- Reagents: Hydrogen bromide

- Equation: CH₂=CH₂ + HBr → CH₃CH₂Br

How can an alkene be converted to an alkylhydrogensulphate? Include the mechanism, reagents, and equation. (3)

- Mechanism: Electrophilic Addition

- Reagents: Concentrated sulphuric acid

- Equation: CH₂=CH₂ + H₂SO₄ → CH₃CH₂OSO₃H

How can an alkylhydrogensulphate be converted to an alcohol? Include the reaction, reagents, and equation. (3)

- Reaction: Hydrolysis

- Reagents: Water

- Equation: CH₃CH₂OSO₃H + H₂O → CH₃CH₂OH + H₂SO₄

How can an alkene be converted to an alcohol? Include the mechanism, reagents, and equation. (5)

- Reaction: Direct Hydration

- Mechanism: Electrophilic Addition

- Reagents: Steam

- Conditions: Phosphoric acid or sulfuric acid catalyst

- Equation: CH₂=CH₂ + H₂O → CH₃CH₂OH

How can an alcohol be converted to an alkene? Include the reaction, mechanism, and equation. (4)

- Reaction: Dehydration

- Mechanism: Elimination

- Reagents: Concentrated sulfuric acid

- Equation: CH₃CH₂OH → CH₂=CH₂ + H₂O

How can a primary or secondary alcohol be converted to an aldehyde or ketone? Include the reaction, reagents, and equations. (5)

- Reaction: Oxidation

- Reagents: Acidified potassium dichromate

- Conditions: Distillation

- Equations:

RCH(OH)R + [O] → RCOR + H₂O

RCH₂OH + [O] → RCHO + H₂O

How can a primary alcohol be converted to a carboxylic acid? Include the reaction, reagents, and conditions. (4)

- Reaction: Oxidation

- Reagents: Acidified potassium dichromate

- Conditions: Reflux, excess acidified potassium dichromate

- Equation: R-CH₂OH + 2[O] → R-COOH + H₂O

How can an aldehyde be converted to a carboxylic acid? Include the reaction, reagents, and conditions. (4)

- Reaction: Oxidation

- Reagents: Acidified potassium dichromate

- Conditions: Reflux

- Equation: R-CHO + [O] → R-COOH

How can an aldehyde or ketone be converted to an alcohol? Include the reaction, mechanism, and reagents. (4)

- Reaction: Reduction

- Mechanism: Nucleophilic Addition

- Reagents: NaBH₄ (aqueous)

- Equation: R₁-COR₂ + 2[H] → R₁R₂CHOH

How can an aldehyde or ketone be converted to a hydroxynitrile? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Addition

- Reagents: KCN + dilute HCl

- Equation: R₁COR₂ + KCN + H⁺ → R₁R₂COHCN

How can an acyl chloride be converted to a carboxylic acid? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic addition-elimination

- Reagents: Water

- Equation: R-COCl + H₂O → R-COOH + HCl

How can an acid anhydride be converted to a carboxylic acid? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic addition-elimination

- Reagents: Water

- Equation: (RCO)₂O + H₂O → 2R-COOH

How can a carboxylic acid be converted to a carboxylate salt? Include the reagents and equation. (2)

- Reagents: NaOH

- Equation: R-COOH + NaOH → R-COONa + H₂O

How can a carboxylic acid and alcohol react to form an ester? Include the reaction type, reagents, and equation. (3)

- Reaction: Esterification

- Reagents: Concentrated sulphuric acid

- Equation: R₁COOH + R₂OH → R₁COOR₂ + H₂O

How can an acyl chloride and alcohol react to form an ester? Include the mechanism and equation. (2)

- Mechanism: Nucleophilic Addition-Elimination

- Equation: R₁COCl + R₂OH → R₁COOR₂ + HCl

How can an acid anhydride and alcohol react to form an ester? Include the mechanism and equation. (2)

- Mechanism: Nucleophilic Addition-Elimination

- Equation: (RCO)₂O + R₂OH → R₁COOR₂ + R₁COOH

How can an acyl chloride be converted to an amide? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Addition-Elimination

- Reagents: Ammonia

- Equation: R-COCl + NH₃ → R-CONH₂ + HCl

How can an acid anhydride be converted to an amide? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Addition-Elimination

- Reagents: Ammonia

- Equation: (RCO)₂O + NH₃ → R-CONH₂ + RCOOH

How can an acyl chloride react with a primary amine to form an N-substituted amide? Include the mechanism and equation. (2)

- Mechanism: Nucleophilic Addition-Elimination

- Equation: R₁COCl + 2R₂-NH₂ → R₁CONHR₂ + R₂-NH₃Cl

How can an acid anhydride react with a primary amine to form an N-substituted amide? Include the mechanism and equation. (2)

- Mechanism: Nucleophilic Addition-Elimination

- Equation: (RCO)₂O + R₂-NH₂ → R₁CONHR₂ + R₁COOH

How can an ester be converted to a carboxylic acid and alcohol? Include the reaction, reagents, and equation. (3)

- Reaction: Hydrolysis

- Reagents: Water and concentrated sulfuric acid

- Equation: R1COOR2 + H2O → R1COOH + R2OH

How can an ester be converted to a carboxylate salt and alcohol? Include the reaction, reagents, and equation. (3)

- Reaction: Hydrolysis

- Reagents: NaOH(aq)

- Equation: R1COOR2 + NaOH → R1COONa + R2OH

How can benzene be converted to nitrobenzene? Include the mechanism, reagents, and equation. (3)

- Mechanism: Electrophilic Substitution

- Reagents: Concentrated sulfuric acid and concentrated nitric acid

- Equation: C6H6 + HNO3 → C6H5NO2 + H2O

How can benzene be converted to phenylketone? Include the mechanism, reagents, and equation. (3)

- Mechanism: Electrophilic Substitution

- Reagents: Acyl chloride, AlCl3

- Equation: C6H6 + RCOCl → C6H5COR + HCl

How can nitrobenzene be converted to phenylamine? Include the reaction, reagents, and equation. (3)

- Reaction: Reduction

- Reagents: Tin, concentrated HCl

- Equation: C₆H₆ + 6[H] → C₆H₅NH₂ + 2H₂O

Flashcard 2

How can a primary amine be converted to a secondary amine? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Substitution

- Reagents: Haloalkane

- Equation: R₁-NH₂ + R₂-Cl → R₁R₂NH + HCl

How can a secondary amine be converted to a tertiary amine? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Substitution

- Reagents: Haloalkane

- Equation: R₁R₂NH + R₃-Cl → R₁R₂R₃N + HCl

How can a tertiary amine be converted to a quaternary ammonium halide salt? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Substitution

- Reagents: Haloalkane

- Equation: R1R2R3N + R4-Cl → R1R2R3R4N+Cl-

How can an amine be converted to an alkylammonium salt? Include the mechanism, reagents, and equation. (3)

- Mechanism: Nucleophilic Substitution

- Reagents: HCl(aq)

- Equation: R1R2R3N + HCl → R1R2R3NHCl

How can a nitrile be converted to an amine? Include the reaction, reagents, and equation. (3)

- Reaction: Reduction

- Reagents: Hydrogen and Nickel Catalyst

- Equation: RCN + 4[H] → RCH2NH2

How can a nitrile be converted to a carboxylic acid? Include the reaction, reagents, and equation. (3)

- Reaction: Hydrolysis

- Reagents: Dilute HCl

- Equation: RCN + HCl + 2H2O → RCOOH + NH4Cl