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OCR A A-Level Organic Chemistry > Chapter 28: Further Synthetic Routes > Flashcards

Chapter 28: Further Synthetic Routes Flashcards

1
Q

What products can benzene react to form?

A
  • Nitrobenzene
  • Halobenzene
  • Alkylbenzene
  • Phenylketone
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2
Q

Benzene to nitrobenzene. Reactants, conditions and mechanism if applicable.

A
  • Reactants: concentrated nitric acid and benzene
  • Conditions: concentrated sulfuric acid catalyst
  • Mechanism: electrophilic substitution
  • HNO3 (conc) + H2SO4 (conc) -> NO2+ + HSO4- + H2O
  • C6H6 + NO2+ -> C6H5NO2 + H+
  • H+ + HSO4- -> H2SO4
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3
Q

Benzene to bromobenzene. Reactants, conditions and mechanism if applicable.

A
  • Reactants: bromine and benzene
  • Conditions: halogen carrier catalyst
  • Mechanism: electrophilic substitution
  • Br2 + FeBr3 -> FeBr4- + Br+
  • C6H6 + Br+ -> C6H5Br + H+
  • H+ + FeBr4- -> FeBr3 + HBr
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4
Q

Benzene to alkylbenzene. Reactants, conditions and mechanism if applicable.

A
  • Reactants: haloalkane and benzene
  • Conditions: halogen carrier catalyst
  • Mechanism: electrophilic substitution
  • Benzene + haloalkane -> alkyl benzene + hydrogen halide
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5
Q

Benzene to phenylketone. Reactants, conditions and mechanism if applicable.

A
  • Reactants: acyl chloride and benzene
  • Conditions: iron (III) chloride/ aluminium chloride
  • Mechanism: electrophilic substitution
  • Benzene + acyl chloride -> phenylketone + hydrogen chloride
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6
Q

What can phenol react to form?

A
  • 2,4,6-tribromophenol
  • Nitrophenol
  • Metal phenoxide
  • Ester
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7
Q

Phenol to 2,4,6-tribromophenol. Reactants, conditions and mechanism if applicable. Give 2 extra details.

A
  • Reactants: phenol and bromine water
  • Conditions: room temperature, no catalyst
  • Mechanism: electrophilic substitution
  • C6H5OH + 3Br2 -> 2,4,6-tribromophenol + 3HBr
  • Bromine water is decolourised
  • A white precipitate (2,4,6-tribromophenol) is formed
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8
Q

Phenol to nitrophenol. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: phenol and dilute nitric acid
  • Conditions: room temperature, no catalyst
  • Mechanism: electrophilic substitution
  • Phenol + dilute nitric acid -> 2-nitrophenol/ 4-nitrophenol + water
  • A mixture of 2-nitrophenol and 4-nitrophenol is formed
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9
Q

Phenol to sodium phenoxide. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: phenol and sodium hydroxide
  • Conditions: room temperature, no catalyst
  • Products: sodium phenoxide and water
  • Neutralisation
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10
Q

Phenol to ester. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: phenol and acid anhydride/ acyl chloride
  • Conditions: room temperature, no catalyst
  • Products: ester and carboxylic acid/ hydrogen chloride
  • Carboxylic acids are not reactive enough to esterify phenol
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11
Q

What can aldehydes react to form?

A
  • Carboxylic acids
  • Primary alcohols
  • Hydroxynitriles
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12
Q

Aldehyde to carboxylic acid. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: aldehyde and [O]
  • Conditions: heat under reflux, K2Cr2O7/ H2SO4
  • Water is not formed as it was already formed in the step going from an alcohol to an aldehyde
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13
Q

Aldehyde to primary alcohol. Reactants, conditions and mechanism if applicable.

A
  • Reactants: aldehyde and 2[H]
  • Conditions: NaBH4/ H2O
  • Mechanism: nucleophilic addition
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14
Q

Aldehyde to hydroxynitrile. Reactants, conditions and mechanism if applicable.

A
  • Reactants: aldehyde and HCN
  • Conditions: NaCN/ H2SO4
  • Mechanism: nucleophilic addition
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15
Q

What can ketones react to form?

A
  • Secondary alcohols
  • Hydroxynitriles
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16
Q

Ketone to secondary alcohol. Reactants, conditions and mechanism if applicable.

A
  • Reactants: ketone and 2[H]
  • Conditions: NaBH4/ H2O
  • Mechanism: nucleophilic addition
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17
Q

Ketone to hydroxynitrile. Reactants, conditions and mechanism if applicable.

A
  • Reactants: ketone and HCN
  • Conditions: NaCN/ H2SO4
  • Mechanism: nucleophilic addition
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18
Q

What can carboxylic acids react to form?

A
  • Esters
  • Acyl chlorides
19
Q

Carboxylic acid to ester. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: carboxylic acid and alcohol
  • Conditions: H2SO4, heat
  • Products: ester and water
  • This reaction is esterification
20
Q

Carboxylic acid to acyl chloride. Reactants, conditions and mechanism if applicable.

A
  • Reactants: carboxylic acid and SOCl2 (thionyl chloride)
  • Products: acyl chloride, sulfur dioxide and hydrogen chloride
  • Conditions: room temperature, no catalyst
21
Q

What can esters react to form?

A
  • Carboxylic acid
  • Carboxylate ion/ carboxylate salt
22
Q

Ester to carboxylic acid. Reactants, conditions and mechanism if applicable. Give 2 extra details.

A
  • Reactants: ester and water
  • Conditions: heat under reflux, aqueous H2SO4
  • Products: carboxylic acid and alcohol
  • This reaction is known as hydrolysis
  • It is reversible (esterification)
23
Q

Ester to carboxylate ion/ carboxylate salt. Reactants, conditions and mechanism if applicable. Give 2 extra details.

A
  • Reactants: ester and hydroxide ion/ NaOH
  • Conditions: heat under reflux (aqueous NaOH if making the carboxylate ion)
  • Products: carboxylate ion/ sodium carboxylate and alcohol
  • This reaction is known as hydrolysis
  • It is irreversible
24
Q

What can acyl chlorides react to form? Which mechanism do acyl chlorides undergo?

A
  • Esters
  • Carboxylic acids
  • Primary amides
  • Secondary amides
  • Nucleophilic addition-elimination
25
Q

Acyl chlorides to ester. Reactants and conditions.

A
  • Reactants: acyl chloride and alcohol
  • Conditions: room temperature, no catalyst
  • Products: ester and hydrogen chloride
26
Q

Acyl chloride to carboxylic acid. Reactants and conditions.

A
  • Reactants: acyl chloride and water
  • Conditions: room temperature, no catalyst
  • Products: carboxylic acid and hydrogen chloride
27
Q

Acyl chloride to primary amide. Reactants and conditions.

A
  • Reactants: acyl chloride and excess ammonia
  • Conditions: room temperature, no catalyst
  • Products: primary amide and ammonium chloride
28
Q

Acyl chlorides to secondary amide. Reactants and conditions.

A
  • Reactants: acyl chloride and primary amine
  • Conditions: room temperature, no catalyst
  • Products: secondary amide and alkyl ammonium chloride
29
Q

What can acid anhydrides react to form?

A
  • Esters
  • Carboxylic acids
  • Primary amides
  • Secondary amides
30
Q

Acid anhydride to ester. Reactants, conditions and mechanism if applicable.

A
  • Reactants: acid anhydride and alcohol
  • Conditions: room temperature, no catalyst
  • Products: ester and carboxylic acid
31
Q

What can haloalkanes react to form?

A
  • (Alcohols)
  • Amines
  • Nitriles
32
Q

What can primary amines react to form?

A
  • Secondary and tertiary amines
  • Alkylammonium salts
33
Q

Haloalkane to primary amine. Reactants, conditions and mechanism if applicable.

A
  • Reactants: haloalkane and excess ethanolic ammonia
  • Conditions: NaOH
  • Products: primary amine, NaX and H2O
  • First step: nucleophilic substitution
34
Q

Haloalkane to secondary amine. Reactants, conditions and mechanism if applicable.

A
  • Reactants: haloalkane and primary amine
  • Conditions: NaOH
  • Products: secondary amine, NaX and H2O
  • First step: nucleophilic substitution
35
Q

Haloalkane to tertiary amine. Reactants, conditions and mechanism if applicable.

A
  • Reactants: haloalkane and secondary amine
  • Conditions: NaOH
  • Products: tertiary amine, NaX and H2O
  • First step: nucleophilic substitution
36
Q

Haloalkane to nitrile. Reactants, conditions and mechanism if applicable.

A
  • Reactants: haloalkane and NaCN/ KCN
  • Conditions: ethanol
  • Products: nitrile and NaX/ KX
  • Mechanism: nucleophilic substitution
37
Q

Amine to alkylammonium salt. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: amine and acid
  • Conditions: room temperature, no catalyst
  • Product: alkylammonium salt
  • Neutralisation
38
Q

What can nitrobenzene react to form?

A
  • Phenylamine
39
Q

Nitrobenzene to phenylamine. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: nitrobenzene + 6[H]
  • Conditions: Sn and concentrated HCl
  • Product: phenylamine + 2H2O
  • Reduction
40
Q

What can amino acids react to form?

41
Q

Amino acid to ester. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: amino acid and alcohol
  • Conditions: heat, aqueous H2SO4
  • Products: ester and water
  • Ester contains NH3+ due to acidic conditions
42
Q

What can nitriles react to form?

A
  • Amines
  • Carboxylic acids
43
Q

Nitrile to amine. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: nitrile and hydrogen
  • Conditions: Ni catalyst
  • Products: amine
  • Reduction
44
Q

Nitrile to carboxylic acid. Reactants, conditions and mechanism if applicable. Give 1 extra detail.

A
  • Reactants: nitrile, water and hydrochloric acid
  • Conditions: heat and dilute HCl
  • Products: carboxylic acid and ammonium chloride
  • Acid hydrolysis

OCR A A-Level Organic Chemistry (20 decks)

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