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Chemistry A Level OCR 50 Organic reactions > Reactions > Flashcards

Reactions Flashcards

1
Q

Alkane + Halogen ⟶

A

Alkane + halogen ⟶ Haloalkane + HX

Free radical substitution (Cl•, Br• etc)
Need UV Light
Initiation, Propagation, Termination

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2
Q

Alkene + H₂ ⟶

A

Alkene + H₂ ⟶ Alkane

Nickel Catalyst @ 150°C

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3
Q

Alkene + Halogen ⟶

A

Alkene + Halogen ⟶ Dihaloalkane

Electrophilic addition
If Bromine used: decolourisation!

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4
Q

Alkene + Hydrogen Halide ⟶

A

Alkene + Hydrogen Halide ⟶ Haloalkane

Electrophilic Addition
Unsymmetrical alkene? major and minor product

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5
Q

Alkene + H₂O (g) ⇌

A

Alkene + H₂O (g) ⇌ Alcohol

Steam hydration 
Phosphoric acide (H₃PO₄) Catalyst @300°C, 60-70atm
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6
Q

Alcohol + Halide ion ⟶

A

Alcohol + Halide ion ⟶ Haloalkane + OH⁻⁻⁻

Nucleophilic substitution
React with NaBr + an acid catalyst (H₂SO₄) + Heat

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7
Q

Alcohol ⟶

A

Alcohol ⟶ Alkene + water

Dehydration/elimination of H₂O
Acid catalyst: Conc. H₂SO₄ or Conc. H₃PO₄ + heat

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8
Q

Alcohol + Oxygen ⟶

A

Alcohol + Oxygen ⟶ Carbon Dioxide + water

Combustion: alcohol = oxidised

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9
Q

Primary Alcohol + [O] ⟶

A

Primary Alcohol + [O] ⟶ Aldehyde + Water

Oxidation
Gently heat in distillation apparatus with H⁺/Cr₂O₇⁻⁻⁻
Distil aldehyde off as formed to prevent COOH forming

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10
Q

Primary Alcohol + 2[O] ⟶

A

Primary Alcohol + 2[O] ⟶ Carboxylic Acid + water

Oxidation
Heat under reflux with excess H⁺/Cr₂O₇⁻⁻⁻
Excess ensures complete oxidation

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11
Q

Secondary Alcohol + [O] ⟶

A

Secondary Alcohol + [O] ⟶ Ketone + water

Oxidation
(distillation) or reflux with H⁺/Cr₂O₇⁻⁻⁻

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12
Q

Tertiary Alcohol + [O] ⟶

A

Tertiary Alcohol + [O] ⟶ CANNOT BE OXIDISED

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13
Q

Haloalkane + OH⁻⁻⁻ ⟶

A

Haloalkane + OH⁻⁻⁻ ⟶ Alcohol + X⁻⁻⁻

Nucleophilic substitution (:OH⁻⁻)
Warm aqueous alkali + heated under reflux
Water can also act as nucleophile but much slower

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14
Q

Benzene + NO₂ ⁺ ⟶

A

Benzene + NO₂ ⁺ ⟶ Nitrobenzene + H⁺

Electrophilic substitution
Conc. HNO₃ and Conc. H₂SO₄ catalyst
50°C for mono nitration

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15
Q

Benzene + Halogen ⟶

A

Benzene + Halogen ⟶ Halobenzene + HX

Electrophilic substitution (Cl ⁺ or Br ⁺ )
Halogen (e.g.Cl₂) + Halogen Carrier catalyst (e.g. AlCl₃/FeCl₃)
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16
Q

Benzene + Haloalkane ⟶

A

Benzene + Haloalkane ⟶ Alkylbenzene + HX

Electrophilic substitution ( CH₃⁺) = alkylation 
Halogen carrier catalyst + reflux +anhydrous conditions 
Friedel-Crafts reaction
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17
Q

Benzene + Acyl chloride ⟶

A

Benzene + Acyl chloride ⟶ Phenylketone + HCl

Electrophilic substitution (CH₃C⁺O) = acylation 
Halogen carrier catalyst + reflux + anhydrous conditions 
Friedel-Crafts reactions
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18
Q

Phenol + HNO₃ ⟶

A

Phenol + HNO₃ ⟶ Nitrophenol + water

Electrophilic substitution
dilute HNO₃, no catalyst (reacts much more readily than benzene)
forms 2 isomers: 2-nitrophenol and 4-nitrophenol

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19
Q

Phenol + Bromine ⟶

A

Phenol + Bromine ⟶ Bromophenol + HBr

Electrophilic substitution
no catalyst + decolourises orange bromine
product = 2,4,6-tribromophenol =antiseptic

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20
Q

Phenol + NaOH ⟶

Phenol + Na ⟶

A

Phenol + NaOH ⟶ Sodiumphenoxide + water
Phenol + Na ⟶ Sodiumphenoxide + H₂
Neutralisation reaction
Phenol = weak acid: not acidic enough to react with carbonates :(

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21
Q

Aldehyde + 2[H] ⟶

A

Aldehyde + 2[H] ⟶ Primary Alcohol

```
Nucleophilic addition (H⁻⁻⁻
Reducing agent = NaBH₄ (supplies hydride ions)
Add water)
~~~

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22
Q

Ketone + 2[H] ⟶

A

Ketone + 2[H] ⟶ Secondary alcohol

```
Nucleophilic addition (H⁻⁻⁻
Reducing agent = NaBH₄ (supplies hydride ions)
Then add water)
~~~

23
Q

Carbonyl + Hydrogen Cyanide ⟶

A

Carbonyl + Hydrogen Cyanide ⟶ Hydroxynitrile

Hydroxynitrile = molecule with OH and CN group
Nucleophilic addition (:CN⁻⁻⁻)
HCN = weak acid, partially dissociates in water ⟶ CN⁻⁻⁻
CN⁻⁻⁻ attacks δ+ carbon on carbonyl group
Extends carbon chain
H⁺ (from H₂O or HCN) bonds to oxygen = hydroxyl group

24
Q

Carboxylic acid + Metal ⟶

A

Carboxylic acid + Metal ⟶ Salt + H₂(g)

Redox reaction/neutralisation

N.B. salts of carboxylic acids end in –oate

25
Q

Carboxylic acid + Metal Carbonate ⟶

A

Carboxylic acid + Metal Carbonate ⟶ Salt + H₂O + CO₂

Neutralisation

26
Q

Carboxylic acid + Alkali ⟶

A

Carboxylic acid + Alkali ⟶ Salt + water

Alkali = metal hydroxide
Neutralisation

27
Q

Carboxylic acid + Metal Oxide ⟶

A

Carboxylic acid + Metal Oxide ⟶ Salt + water

Neutralisation

28
Q

Carboxylic acid + SOCl₂ ⟶

A

Carboxylic acid + SOCl₂ ⟶ Acyl Chloride + HCl + SO₂

SOCl₂ = thionyl chloride
OH group replaced by Cl group

29
Q

Acyl Chloride + Alcohol ⟶

A

Acyl Chloride + Alcohol ⟶ Ester + HCl

Much easier + faster way to make an ester than with carboxylic acid + alcohol

30
Q

Acyl Chloride + phenol ⟶

A

Acyl Chloride + phenol ⟶ Ester + HCl

Faster than using a carboxylic acid + phenol

31
Q

Acyl Chloride + Water ⟶

A

Acyl Chloride + Water ⟶ Carboxylic acid + HCl

Vigorous reaction with cold water

32
Q

Acyl Chloride + Ammonia ⟶

A

Acyl Chloride + Ammonia ⟶ Primary Amide + HCl

In the lab: HCl reacts with NH₃: produce NH₄Cl

33
Q

Acyl Chloride + Amine ⟶

A

Acyl Chloride + Amine ⟶ Secondary Amide + HCl

Use a primary amine

34
Q

Alcohol + Carboxylic acid ⟶

A

Alcohol + Carboxylic acid ⟶ Ester + Water

Heat with acid catalysts (H₂SO₄)
Reversible reaction: separate product as it forms using fractional distillation
N.B Oxygen in ester bonds comes from alcohol

35
Q

Alcohol + Acid Anhydride ⟶

A

Alcohol + Acid Anhydride ⟶ Ester + carboxylic Acid

Acid anhydride = 2 carboxylic acid molecules
slow: speed up by warming

36
Q

Ester + water ⇌

A

Ester + water ⇌ Carboxylic acid + alcohol

Acid hydrolysis
Reflux ester with hot quests acid e.g. HCl, H₂SO₄ (dilute)

37
Q

Ester + Alkali ⟶

A

Ester + Alkali ⟶ Carboxylate salt + alcohol

Base hydrolysis
reflux ester with a hot aqueous alkali e.g. NaOH (dilute)

38
Q

Amine + Acid ⟶

A

Amine + Acid ⟶ Ammonium salt

Neutralisation: amines = bases

39
Q

Ammonia + Haloalkane ⟶

A

Ammonia + Haloalkane ⟶ Primary Aliphatic Amine + NH₄X

Nucleophilic substitution
excess ethanol ammonia used
forms a primary aliphatic (no benzene) amine

40
Q

Primary Amine + Haloalkane ⟶

A

Primary Amine + Haloalkane ⟶ Secondary Aliphatic Amine + NH₄X

Nucleophilic substitution
Substitution continues: get a mixture of primary, secondary + tertiary amines + quaternary ammonium salts (separate by fractional distillation)

41
Q

Nitrobenzene + 6[H] ⟶

A

Nitrobenzene + 6[H] ⟶ Phenylamine + 2H₂O

Heating under reflux with tin catalysts + conc. HCl
if 2 substitutions: 12[H] and 4H₂O !!
Must add NaOH (phenyl amine +HCl ⟶ salt :( )
Reduction

42
Q

Amino Acid + Acid ⟶

A

Amino Acid + Acid ⟶ Salt

If pH is lower than isoelectric point, amino acid behaves as a base: amino group reacts
NH₂ ⟶ NH₃⁺ = cation

43
Q

Amino Acid + Base ⟶

A

Amino Acid + Base ⟶ Salt + Water

If pH is higher than isoelectric point, amino acid behaves as an acid: COOH group reacts
COOH ⟶ COO⁻⁻⁻ = anion

44
Q

Amino acid + Alcohol ⟶

A

Amino acid + Alcohol ⟶ Ester + water

Strong acid catalyst (H₂SO₄)

45
Q

Amino Acid + Amino Acid ⟶

A

Amino Acid + Amino Acid ⟶ Amide (dipeptide)

Condensation reaction: elimination of H₂O
Forms a dipeptide = secondary amide

46
Q

Dicarboxylic acid + Diamine ⟶

A

Dicarboxylic acid + Diamine ⟶ Polyamide + water

Condensation polymer (loses H₂O)

47
Q

Dicarboxylic acid + Diol ⟶

A

Dicarboxylic acid + Diol ⟶ Polyester + water

Condensation polymer (loses H₂O)

48
Q

H⁺

Polyamide + 2H₂O ⟶

A

H⁺
Polyamide + 2H₂O ⟶ Dicarboxylix acid + diamine

Polyamide hydrolyses more easily with an acid than a base = acid hydrolysis

49
Q

Polyester + 2NaOH ⟶

A

Polyester + 2NaOH ⟶ Dicarboxylix acid salt + Diol

Polyesters hydrolysis more easily with a base than an acid = base hydrolysis

50
Q

Haloalkane + CN⁻⁻⁻ ⟶

A

Haloalkane + CN⁻⁻⁻ ⟶ Nitrile + X⁻⁻⁻

Nucleophilic substitution
Reflux haloalkane with potassium cyanide in ETHANOL SOLVENT

51
Q

Nitrile + 4[H] ⟶

A

Nitrile + 4[H] ⟶ Primary amine

Reduction (method 1)
Use Lithium Aluminium Hydride: LiAlH₄, which is a strong reducing agent, and dilute acid

52
Q

Nitrile + 2H₂ (g) ⟶

A

Nitrile + 2H₂ (g) ⟶ Primary amine

Reduction (method 2 - used in industry)
Hydrogen gas, metal catalyst (e.g. Platinum or Nickel)
High temp + pressure

N.B Nitriles can also be reduced with sodium metal and ethanol !!

53
Q

Nitrile + 2H₂O + HCl ⟶

A

Nitrile + 2H₂O + HCl ⟶ Carboxylic acid + NH₄Cl

Acid hydrolysis
reflux nitrile in dilute HCl (with heat)

54
Q

Haber Process

A

N₂ (g) + 3H₂ (g) ⇌ 2NH₃ (g)

Forward reaction = exothermic
High pressure favours forward reaction

BUT
low temp decreases yield so compromise @ 450°C
High pressure = dangerous & expensive compromise of 200 atm.
Finely divided porous iron catalyst

Chemistry A Level OCR 50 Organic reactions (1 decks)

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