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Organic Compound Formation Flashcards

1
Q

Alkene to alkane

A
  • Alkene + Hydrogen gas
  • Nickel catalyst
  • 150°C

= Alkane

Or:

  • Alkene + Hydrogen gas
  • Platinum/ palladium catalyst
  • Room temperature

= Alkane

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2
Q

Alkyne to alkane

A
  • Alkyne+ 2 Hydrogen gas molecules
  • Nickel catalyst
  • 150°C

= Alkane

Or:

  • Alkyne + 2 Hydrogen
  • Platinum catalyst
  • Room temperature
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3
Q

Alkyl halide to alkane

A
  • Alkyl halide
  • Zinc-copper couple
  • Aqueous alcohol
  • Room temperature

= alkane

Or: Wurtz synthesis
- 2 Alkyl halide+ 2 Sodium metal
- Dry ether
- Heat

= Alkane (carbon atoms doubled) + 2 NaX

Or: Grignard reagent
Preparation;
- Alkyl halide + Magnesium metal
- Dry ether

= Grignard reagent (RMgX)

  • Grignard reagent + Water
  • Aqueous hydrochloric or sulphuric acid

= Alkane + Mg(OH)X

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4
Q

Alkyl halide to alkane (in which the number of carbon atoms has doubled)

A

Wurtz synthesis
- 2 Alkyl halide + 2 Sodium metal
- Dry ether
- Heat

= Alkane (carbon atoms doubled) + 2 NaX

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5
Q

Preparation of Grignard reagent

A
  • Alkyl halide + Magnesium metal
  • Dry ether

= Grignard reagent (RMgX)

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6
Q

What is soda lime?

A

Mixture of CaO and NaOH/ KOH

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7
Q

Decarboxylation

A
  • Carboxylic acid
  • Sodium Hydroxide
  • Heat
    = Sodium salt of a carboxylic acid
  • Sodium salt of a carboxylic acid
  • Soda lime
  • Heat

= Alkane (with one less Carbon atom) + sodium carbonate

Or: Starting with a sodium salt of a carboxylic acid

  • Sodium salt of a carboxylic acid
  • Soda lime
  • Heat

= Alkane (with one less Carbon atom) + sodium carbonate

Or:
- Sodium salt of a carboxylic acid + Sodium hydroxide
- Heat, fused

= Alkane (with one less Carbon atom) + sodium carbonate

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8
Q

Aluminum carbide to methane

A
  • Aluminum carbide + Hot water/ Dilute HCl

= 3 Methane + 4 Aluminum Chloride

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9
Q

Sodium ethanoate (2C) to methane (1C)

A
  • Sodium ethanoate + Sodium hydroxide
  • Heat

= Methane + Sodium carbonate

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10
Q

Alkane to alkyl halide

A
  • Alkane + Chlorine/ Bromine gas
  • UV light

= Alkyl halide + hydrochloric/ hydrobromic acid

Excess chlorine/ bromine used:
- Alkane + 2 Chlorine/ Bromine gas
- UV light

= Carbon tetrachloride/ tetrabromide + hydrochloric/ hydrobromic acid

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11
Q

Alkane to nitroalkane

A
  • Alkane + Nitric acid
  • 400°C

= Nitroalkane + Water

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12
Q

Methane to carbon dioxide

A
  • methane + 2 oxygen

= Carbon dioxide + 2 Water

In insufficient oxygen:
- methane + oxygen

= Carbon dioxide + Water

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13
Q

Alcohol to alkene

A
  • Alcohol
  • Concentrated sulphuric acid/ phosphoric acid
  • 180°C

= Alkene + Water

Or:
- Alcohol
- Aluminum oxide catalyst
- 350°C

= Alkene + Water

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14
Q

Alkyl halide to alkene

A
  • Alkyl halide
  • KOH/ NaOH
  • Ethanol
  • Heat

= Alkene + hydrochloric/ Hydrobromic

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15
Q

Alkyne to alkene

A
  • Alkyne + Hydrogen gas
  • Lindlar’s catalyst / poisoned Palladium and Barium sulphate

=Alkene

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16
Q

Vic dihalide to alkene

A
  • Vic dihalide + Zinc
  • Methanol
  • Heat

= Alkene + ZnX2

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17
Q

Alkene to vic dihalide

A
  • Alkene + Halogen
  • CCl4 (tetrachloromethane)

= Vic dihalide

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18
Q

Alkene to a halogen alcohol

A
  • Alkene
  • Halogen, Water

= Halogen alcohol

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19
Q

Alkene to alkyl halide

A

Markownikoff’s rule of unsymmetrical alkenes
- Unsymmetrical alkene + Hydrogen halide(halogen acid HX)

= Halogen atom is attached to the carbon atom with fewer hydrogen atoms

Or: For symmetrical alkenes
- Alkene + HBr (only works for Br)
- Organic peroxide eg H3COOCH3

= Halogen atom is attached to the carbon atom with more hydrogen atoms

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20
Q

Alkene to alkyl hydrogen sulphate

A
  • Alkene
  • Concentrated sulphuric acid
  • 0-15°C

= Alkyl hydrogen sulphate

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21
Q

Alkene to alcohol

A
  • Alkene
  • H+ / H2O, warm

= Alcohol

Same but in words:
- Alkene
- i) Conc sulphuric acid, ii) Water/warm
= Alcohol

Or: Longer route
- Alkene
- Concentrated sulphuric acid
- 0-15°C
= alkyl hydrogen sulphate

  • Alkyl hydrogen sulphate
  • Water (H20), warm
    = Alcohol
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22
Q

Alkene to diol

A
  • Alkene
  • KMnO4(aq)/ -OH or NaOH

= Diol

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23
Q

Alkene to epoxyalkane

A
  • Alkene + 1/2 oxygen gas
  • Silver metal catalyst

= epoxyalkane

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24
Q

Epoxyalkane to Diol

A
  • Epoxyalkane + Water

= Diol

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25
Q

Alkene to ozonide

A
  • Alkene + Ozone
  • Tetrachloromethane
  • < 20°C

= Ozonide

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26
Q

Ozonide to carbonyl compounds (Aldehydes and ketones)

A
  • Ozonide + Water
  • Zinc dust
  • Ethanoic acid

= 2 carbonyl compounds

(Symmetrical alkene= one type of carbonyl compound
Unsymmetrical = two types of carbonyl compound)

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27
Q

Butane to ethanal

A
  • Butane + Ozone
  • Tetrachloromethane
  • < 20°C

=ozonide

  • Ozonide + Water
  • Zinc dust
  • Ethanoic acid

= Ethanal

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28
Q

Alkene to polymer

A
  • Alkene
  • High temperature
  • High pressure
  • Catalyst

= Polymer

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29
Q

Dihalogen compound to alkyne

A
  • Dihalogen compound
  • Excess KOH \ Ethanol
  • Heat

= Alkyne + 2HX

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30
Q

Calcium carbide to ethyne

A
  • Calcium carbide + 2Water
    = Calcium hydroxide + Ethyne
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31
Q

Calcium carbonate to ethyne

A
  • Calcium carbonate
  • Heat

= Calcium oxide (quick lime) + Carbon dioxide

  • Calcium oxide + 3 Carbon atoms
  • 2000- 3000°C

=Calcium dicarbide + Carbon dioxide

  • Calcium carbide + 2Water
    = Calcium hydroxide + Ethyne
32
Q

Alkyne to tetra halogen

A
  • Alkyne + 2 Chlorine/ Bromine gas

= tetrahalogen compound

33
Q

Alkyne to gem dihalide

A
  • Alkyne + Hydrogen halide

= Gem dihalide
(According to Markownikoff’s rule)

34
Q

Ethyne to ethanal

A
  • Ethyne + Water
  • Dilute sulphuric acid/ Mercury(ii) sulphate catalyst
  • 60°C

= Ethanal (aldehyde)

All other alkynes form ketones from this

35
Q

Alkyne to ketone

A
  • Alkyne + Water
  • Dilute sulphuric acid/ Mercury(ii) sulphate catalyst
  • 60°C

= Ketone

(Only if the alkyne is anything but ethyne)

36
Q

Ethyne to benzene

A
  • 3 Ethyne
  • Organo-nickel catalyst / iron catalyst
  • 60°C
    = Benzene
37
Q

Benzoic acid to benzene

A

(Decarboxylation)

  • Benzoic acid + Sodium hydroxide

= Sodium benzoate (sodium salt of a carboxylic acid) + Water

  • Sodium benzoate
  • Sodalime
  • Heat

= Benzene + Sodium carbonate

38
Q

Sodium benzoate to benzene

A

(Decarboxylation)

  • Sodium benzoate
  • Sodalime
  • Heat

= Benzene + Sodium carbonate

39
Q

Phenol to benzene

A
  • Phenol + Zinc
  • Heat

= Benzene + Zinc Oxide

40
Q

Benzene diazonium chloride to benzene

A
  • Benzene diazonium chloride
  • Water / hydrophosphorous acid

= Benzene

41
Q

Benzene to nitrobenzene

A
  • Benzene + Nitric acid
  • Concentrated sulphuric acid

= Nitrobenzene + Water

42
Q

Benzene to benzenesulphonic acid

A
  • Benzene + Fuming sulphuric acid

= Benzenesulphonic acid + Water

43
Q

Benzene to a benzene with halogen attached

A
  • Benzene + Halogen gas
  • Halogen carrier catalyst (Iron(iii) chloride, aluminum chloride or bromide of either)

= Benzene with halogen attached + Hydrogen halogen

44
Q

Benzene to methylbenzene

A
  • Benzene + Alkyl halide (specifically chlormethane)
  • Aluminum chloride/ bromide catalyst

= Methylbenzene + Hydrogen halogen

45
Q

Benzene to alkylated benzene

A
  • Benzene + Alkyl halide
  • Aluminum chloride/ bromide catalyst

= Methylbenzene + Hydrogen halogen

Or:
- Benzene + Alkene
- Concentrated sulphuric or phosphoric acid

= Alkylated benzene

46
Q

Benzene to aromatic ketone

A
  • Benzene + Ketohalogen
  • Aluminum chloride

= aromatic ketone + hydrogen halogen

47
Q

Benzene to cyclohexane

A
  • Benzene + 3 Hydrogen gas
  • Nickel catalyst
  • 150°C

=Cyclohexane

48
Q

Benzene to 1,2,3,4,5,6-hexachlorocyclohexane

A
  • Benzene + 3 chlorine gas
  • U.V radiation
    = 1,2,3,4,5,6-hexachlorocyclohexane
49
Q

Ethylbenzene to chloroethylbenzene

A
  • Ethylbenzene + chlorine gas
  • U.V radiation
    = chloroethylbenzene
50
Q

Bromobenzene to methylbenzene

A
  • Bromobenzene + iodomethane + 2 Sodium metal
  • Dry ether

= Methylbenzene + Sodium bromide + sodium iodide

51
Q

Methylbenzene to methylcyclohexane

A
  • Methylbenzene + 3 Hydrogen gas
  • Nickel catalyst
  • 150°C

=Methylcyclohexane

52
Q

Methylbenzene to chloromethylbenzene

A
  • Methylbenzene + Chlorine gas
  • U.V
    = chloromethylbenzene + hydrogen chloride
53
Q

Methylbenzene to benzoic acid

A
  • Methylbenzene
  • H+/ MnO4- (acidified KMnO4- strong) or H+/ Cr2072-
    = Benzoic acid

Or: longer route
- Methylbenzene
- H+ / MnO2 (Manganese(iv) oxide- weak)
= Benzaldehyde

  • Benzaldehyde
  • H+ / MnO2
    = Benzoic acid
54
Q

Methylbenzene to benzaldehyde

A
  • Methylbenzene
  • H+ / MnO2
    = Benzaldehyde
55
Q

Alcohol to alkyl halide (direct)

A

(Preferred)
- Alcohol + thionyl chloride (SOCl2)
- Pyridine
- Heat
= Alkyl halide + Sulphur dioxide + hydrogen chloride

Or: Reaction with hydrogen halide
- Alcohol + HX

= Alkyl halide + Water

Or:
- Alcohol + phosphorus(III) chloride
- Heat
= Alkyl halide + Phosphorus acid

Or:

  • Alcohol + phosphorus(v) chloride
  • Heat
    = Alkyl halide + hydrogen chloride + phosphoryl chloride

*Or: HCl in the presence of anhydrous zinc chloride *
- Alcohol + HCl
- Anhydrous zinc chloride

= Alkyl halide + Water

56
Q

Alcohol to alkyl bromide

A
  • Alcohol
  • Phosphorus/ Bromine liquid (P/Br2)

= Alkyl bromide

Or: Using potassium bromide and concentrated sulphuric acid
- Alcohol
- KBr / concentrated sulphuric acid

= Alkyl bromide

Alcohol to alkyl iodide
- Alcohol
- P/ I2
= Alkyl iodide

Or: Using hydroiodic acid
- Alcohol
- Potassium iodide/ concentrated phosphoric acid

57
Q

Silver salt of carboxylic acid to alkyl halide

A

(Alkyl halide with one carbon less) - Decarboxylation
- Silver salt of carboxylic acid +X2

= Alkyl halide + Carbon dioxide + AgX

X= Cl or Br

58
Q

Alkyl chloride to alkyl bromide
Or Alkyl chloride to alkyl iodide

A
  • Alkyl chloride + KBr or KI
  • Methanol (CH3OH)

= Alkyl bromide / Alkyl iodide respectfully

59
Q

Alkyl halide to nitrile compound

A
  • Alkyl halide + KCN (potassium cyanide) or NaCN (Sodium cyanide)
  • Ethanol
  • Heat

= Alkyl nitrile + KBr or NaBr

60
Q

Alkyl halide to amine

A
  • Alkyl halide + 2 Ammonia
  • Heat

= Amine (primary) + Ammonium chloride

61
Q

Primary amine to secondary amine

A
  • Primary amine + Alkyl halide

= Secondary amine

62
Q

Secondary amine to tertiary amine

A
  • Secondary amine + Alkyl halide

= Tertiary amine

63
Q

Tertiary amine to quaternary ammonium salt

A
  • Tertiary amine + Alkyl halide

= Quaternary ammonium salt

64
Q

Alkyl halide to ether

A
  • Alkyl halide + Sodium alkoxide (RONa)

= Ether + NaX

Or:
- Alkyl halide + Potassium alkoxide (ROK)

= Ether + KX

65
Q

Alkoxide formation

A
  • Alcohol + K or Na metal

= Alkoxide

66
Q

Phenoxide formation

A
  • Phenol + KOH or NaOH

= Phenoxide + Water

67
Q

Carbonyl compund (aldehyde, ketone) to gem dihalide

A
  • Carbonyl compound + PX5
    X= Cl or Br

= Gem dihalide (both halogens on same C atom) + POCl

68
Q

Dihalogen compound to alkyne

A
  • Dihalogen compound
  • Excess KOH/ Ethanol
  • Heat

= Alkyne + 2HX

69
Q

Benzene to aryl halide

A
  • Benzene + X2
  • Halogen carrier eg FeX3, AlX3
    X= Cl or Br
  • Heat
70
Q

Benzene diazonium chloride to chlorobenzene

A
  • Benzene diazonium chloride
  • Copper(II) chloride /HCl
  • Warm

= Chlorobenzene + Nitrogen gas

71
Q

Benzene diazonium chloride to bromobenzene

A
  • Benzene diazonium bromide
  • Copper(II) bromide /HBr
  • Warm

= Bromobenzene + Nitrogen gas

72
Q

Benzene diazonium chloride to fluorobenzene

A
  • Benzene diazonium chloride
  • Sodium tetrafluoroborate (NabF4)
  • Heat

= Fluorobenzene + Nitrogen gas

73
Q

Benzene diazonium chloride to Iodobenzene

A
  • Benzene diazonium chloride
  • KI
  • Warm

= Iodobenzene + Nitrogen gas

74
Q

Benzeneamime to benzene diazonium chloride

A
  • Benzeneamine
  • NaNO2 (sodium nitrite) / dilute HCl
  • 0°C
    = Benzene diazonium chloride
75
Q

Phenol to aryl halide

A
  • Phenol + PX5

= Aryl halide + POX3 + HCl

UACE Chemistry (27 decks)

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