Organic Compound Formation Flashcards

(75 cards)

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
Alkene to ozonide
- Alkene + Ozone - Tetrachloromethane - < 20°C = Ozonide
26
Ozonide to carbonyl compounds (Aldehydes and ketones)
- Ozonide + Water - Zinc dust - Ethanoic acid = 2 carbonyl compounds (Symmetrical alkene= one type of carbonyl compound Unsymmetrical = two types of carbonyl compound)
27
Butane to ethanal
- Butane + Ozone - Tetrachloromethane - < 20°C =ozonide - Ozonide + Water - Zinc dust - Ethanoic acid = Ethanal
28
Alkene to polymer
- Alkene - High temperature - High pressure - Catalyst = Polymer
29
Dihalogen compound to alkyne
- Dihalogen compound - Excess KOH \ Ethanol - Heat = Alkyne + 2HX
30
Calcium carbide to ethyne
- Calcium carbide + 2Water = Calcium hydroxide + Ethyne
31
Calcium carbonate to ethyne
- 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
Alkyne to tetra halogen
- Alkyne + 2 Chlorine/ Bromine gas = tetrahalogen compound
33
Alkyne to gem dihalide
- Alkyne + Hydrogen halide = Gem dihalide (According to Markownikoff’s rule)
34
Ethyne to ethanal
- Ethyne + Water - Dilute sulphuric acid/ Mercury(ii) sulphate catalyst - 60°C = Ethanal (aldehyde) All other alkynes form ketones from this
35
Alkyne to ketone
- Alkyne + Water - Dilute sulphuric acid/ Mercury(ii) sulphate catalyst - 60°C = Ketone (Only if the alkyne is anything but ethyne)
36
Ethyne to benzene
- 3 Ethyne - Organo-nickel catalyst / iron catalyst - 60°C = Benzene
37
Benzoic acid to benzene
(Decarboxylation) - Benzoic acid + Sodium hydroxide = Sodium benzoate (sodium salt of a carboxylic acid) + Water - Sodium benzoate - Sodalime - Heat = Benzene + Sodium carbonate
38
Sodium benzoate to benzene
(Decarboxylation) - Sodium benzoate - Sodalime - Heat = Benzene + Sodium carbonate
39
Phenol to benzene
- Phenol + Zinc - Heat = Benzene + Zinc Oxide
40
Benzene diazonium chloride to benzene
- Benzene diazonium chloride - Water / hydrophosphorous acid = Benzene
41
Benzene to nitrobenzene
- Benzene + Nitric acid - Concentrated sulphuric acid = Nitrobenzene + Water
42
Benzene to benzenesulphonic acid
- Benzene + Fuming sulphuric acid = Benzenesulphonic acid + Water
43
Benzene to a benzene with halogen attached
- Benzene + Halogen gas - Halogen carrier catalyst (Iron(iii) chloride, aluminum chloride or bromide of either) = Benzene with halogen attached + Hydrogen halogen
44
Benzene to methylbenzene
- Benzene + Alkyl halide (specifically chlormethane) - Aluminum chloride/ bromide catalyst = Methylbenzene + Hydrogen halogen
45
Benzene to alkylated benzene
- Benzene + Alkyl halide - Aluminum chloride/ bromide catalyst = Methylbenzene + Hydrogen halogen Or: - Benzene + Alkene - Concentrated sulphuric or phosphoric acid = Alkylated benzene
46
Benzene to aromatic ketone
- Benzene + Ketohalogen - Aluminum chloride = aromatic ketone + hydrogen halogen
47
Benzene to cyclohexane
- Benzene + 3 Hydrogen gas - Nickel catalyst - 150°C =Cyclohexane
48
Benzene to 1,2,3,4,5,6-hexachlorocyclohexane
- Benzene + 3 chlorine gas - U.V radiation = 1,2,3,4,5,6-hexachlorocyclohexane
49
Ethylbenzene to chloroethylbenzene
- Ethylbenzene + chlorine gas - U.V radiation = chloroethylbenzene
50
Bromobenzene to methylbenzene
- Bromobenzene + iodomethane + 2 Sodium metal - Dry ether = Methylbenzene + Sodium bromide + sodium iodide
51
Methylbenzene to methylcyclohexane
- Methylbenzene + 3 Hydrogen gas - Nickel catalyst - 150°C =Methylcyclohexane
52
Methylbenzene to chloromethylbenzene
- Methylbenzene + Chlorine gas - U.V = chloromethylbenzene + hydrogen chloride
53
Methylbenzene to benzoic acid
- 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
Methylbenzene to benzaldehyde
- Methylbenzene - H+ / MnO2 = Benzaldehyde
55
Alcohol to alkyl halide (direct)
(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
Alcohol to alkyl bromide
- 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
Silver salt of carboxylic acid to alkyl halide
(Alkyl halide with one carbon less) - Decarboxylation - Silver salt of carboxylic acid +X2 = Alkyl halide + Carbon dioxide + AgX X= Cl or Br
58
Alkyl chloride to alkyl bromide Or Alkyl chloride to alkyl iodide
- Alkyl chloride + KBr or KI - Methanol (CH3OH) = Alkyl bromide / Alkyl iodide respectfully
59
Alkyl halide to nitrile compound
- Alkyl halide + KCN (potassium cyanide) or NaCN (Sodium cyanide) - Ethanol - Heat = Alkyl nitrile + KBr or NaBr
60
Alkyl halide to amine
- Alkyl halide + 2 Ammonia - Heat = Amine (primary) + Ammonium chloride
61
Primary amine to secondary amine
- Primary amine + Alkyl halide = Secondary amine
62
Secondary amine to tertiary amine
- Secondary amine + Alkyl halide = Tertiary amine
63
Tertiary amine to quaternary ammonium salt
- Tertiary amine + Alkyl halide = Quaternary ammonium salt
64
Alkyl halide to ether
- Alkyl halide + Sodium alkoxide (RONa) = Ether + NaX Or: - Alkyl halide + Potassium alkoxide (ROK) = Ether + KX
65
Alkoxide formation
- Alcohol + K or Na metal = Alkoxide
66
Phenoxide formation
- Phenol + KOH or NaOH = Phenoxide + Water
67
Carbonyl compund (aldehyde, ketone) to gem dihalide
- Carbonyl compound + PX5 X= Cl or Br = Gem dihalide (both halogens on same C atom) + POCl
68
Dihalogen compound to alkyne
- Dihalogen compound - Excess KOH/ Ethanol - Heat = Alkyne + 2HX
69
Benzene to aryl halide
- Benzene + X2 - Halogen carrier eg FeX3, AlX3 X= Cl or Br - Heat
70
Benzene diazonium chloride to chlorobenzene
- Benzene diazonium chloride - Copper(II) chloride /HCl - Warm = Chlorobenzene + Nitrogen gas
71
Benzene diazonium chloride to bromobenzene
- Benzene diazonium bromide - Copper(II) bromide /HBr - Warm = Bromobenzene + Nitrogen gas
72
Benzene diazonium chloride to fluorobenzene
- Benzene diazonium chloride - Sodium tetrafluoroborate (NabF4) - Heat = Fluorobenzene + Nitrogen gas
73
Benzene diazonium chloride to Iodobenzene
- Benzene diazonium chloride - KI - Warm = Iodobenzene + Nitrogen gas
74
Benzeneamime to benzene diazonium chloride
- Benzeneamine - NaNO2 (sodium nitrite) / dilute HCl - 0°C = Benzene diazonium chloride
75
Phenol to aryl halide
- Phenol + PX5 = Aryl halide + POX3 + HCl