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Chemistry > Alkanes - Hydroxy Cpds > Flashcards

Alkanes - Hydroxy Cpds Flashcards

1
Q

Alkane –> Bromoalkane

Observations?

A

Free radical substitution
Br2 in CCl4, UV light

Orange-red solution decolourises.

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2
Q

Alkene –> Alkane

A

Reduction
H2, Ni, heat
/Pt/Pd rtp

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3
Q

Alkene –> Alcohol

  1. Lab method
  2. Industrial method
A

Electrophilic Addition

  1. cold conc H2SO4, then H2O, heat
  2. H2O g, conc H3PO4 on silica support, 70 atm 300deg
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4
Q

Alkene –> Dibromoalkane

Observations?

A

Electrophilic Addition
Br2 in CCl4, in the dark

Orange-red solution decolourises.

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5
Q

Alkene –> Halohydrin C(OH)C(Br)

Observations?

A

Electrophilic Addition
Br2 (aq)

Orange solution decolourises.

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6
Q

Alkene –> Monobromoalkane

A 
Electrophilic Addition
dry HBr (g)
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7
Q

Alkene –> Carboxylic acid,
CO2, H2O (sometimes)

Observations?

A

(Strong) Oxidation
KMnO4 (aq), dilute H2SO4 (aq), heat

Purple solution decolourises

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8
Q

Alkene –> Diol
C(OH)C(OH)

Observations?

A

Mild Oxidation
cold KMnO4 (aq), dilute H2SO4 (aq)
or cold KMnO4 (aq), dilute NaOH (aq)

Purple solution decolourises
Brown-black ppt of MnO2 formed

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9
Q

Alkene –> C(O-Na+)C(O-Na+)

Observations?

A 
Mild Oxidation
cold KMnO4 (aq), dilute NaOH (aq)

Purple solution decolourises
Brown-black ppt of MnO2

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10
Q

Bromoalkane –> Alkene

A

Elimination

ethanolic KOH, heat

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11
Q

Alcohol –> Alkene

A

Elimination
excess conc H2SO4, heat
/Al2O3, heat
/H3PO4, heat

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12
Q

Benzene –> Bromobenzene

A

Electrophilic Substitution

Br2 (l), anhydrous FeBr3 / Fe

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13
Q

Benzene –> Methylbenzene

A 
Electrophilic Substitution (Friedel Crafts Alkylation)
CH3Cl (l), anhydrous FeCl3 / AlCl3
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14
Q

Benzene –> Nitrobenzene

A

Electrophilic Substitution

conc HNO3, conc H2SO4, heat (55deg)

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15
Q

Methylbenzene –> Methylbromobenzene

Also: where would Br attach?

A

Electrophilic Substitution
Br2 (l), anhydrous FeBr3

Br will attach on 2,4

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16
Q

Methylbenzene –> Methylnitrobenzene

Also: where would NO2 attach?

A

Electrophilic Substitution
conc HNO3, conc H2SO4, (30deg)

NO2 will attach on 2,4

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17
Q

Propylbenzene –> Benzoic acid

A

(Side-chain) Oxidation

KMnO4 (aq), dil. H2SO4 (aq), heat

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18
Q

Halogenoethane –> Propylnitrile

A

Nucleophilic Substitution

ethanolic KCN, heat

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19
Q

Halogenoalkane –> Alcohol

A

Nucleophilic Substitution

NaOH(aq) heat

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20
Q

Halogenoalkane –> Amine

A

Nucleophilic Substitution

excess conc NH3 (aq) in ethanol, heat in sealed tube

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21
Q

Halogenoethane –> Methoxyethane (Ether)

A

Nucleophilic Substitution

Methanol, Na (to generate CH3O- nucleophile)

22
Q

Nitrile –> Carboxylic Acid

A

Acid hydrolysis

H2SO4 (aq), heat

23
Q

Nitrile –> Amine

A

Reduction

LiAlH4 in dry ether or H2, Ni, heat

24
Q

Nitrile –> COO’Na+

A

Basic hydrolysis

NaOH (aq), heat

25
Alcohol --> Bromoalkane
Nucleophilic Substitution PBr3/SOBr2 / KBr(s), conc H2SO4, heat (to generate HBr) / dry HBr, heat
26
Alcohol --> Chloroalkane
Nucleophilic Substitution PCl5/PCl3/SOCl2 rtp or HCl(g), anhydrous ZnCl2, heat
27
Alcohol --> Iodoalkane
Nucleophilic Substitution red P, I2, heat (to produce PI3) / KI, conc H2SO4, heat (to generate HI) / dry HI, heat
28
Ethanol --> Methanoic acid/ COO-Na+ | Observations?
Oxidation (Iodoform test) I2 (aq), NaOH (aq), warm Yellow ppt formed
29
Alcohol --> Aldehyde Observations?
Oxidation of primary alcohol K2Cr2O7 (aq), H2SO4 (aq), heat with immediate distillation
30
Alcohol --> Carboxylic acid Observations?
Oxidation of primary alcohol K2Cr2O7 (aq), H2SO4 (aq), heat under reflux Orange solution turns green /KMnO4 (aq), H2SO4 (aq), heat under reflux Purple KMnO4 decolourises
31
Alcohol --> Ketone Observations?
Oxidation of secondary alcohol K2Cr2O7 (aq), H2SO4 (aq), heat under reflux Orange solution turns green /KMnO4 (aq), H2SO4 (aq), heat under reflux Purple KMnO4 decolourises
32
Alcohol --> CO-Na+
Redox Na (s)
33
Aldehyde --> Alcohol
Reduction LiAlH4 in dry ether/ NaBH4/ H2, Ni, heat
34
Ketone --> Alcohol
Reduction | LiAlH4 in dry ether
35
Alcohol --> Ester | Two methods
Condensation - Esterification RCOOH, conc H2SO4, heat - Acylation RCOCl, rtp
36
Phenol --> Sodium phenoxide
Acid-base NaOH (aq) or Acid-metal/Reduction Na (s)
37
Phenol --> trinitrophenol
Electrophilic Substitution | conc HNO3, rtp
38
Phenol --> mononitrophenol
Electrophilic Substitution | dil. HNO3, rtp
39
Phenol --> tribromophenol Observations?
Electrophilic Substitution Br2(aq), rtp Rapid decolourisation of orange Br2, white ppt formed
40
Phenol --> monobromophenol
Electrophilic Substitution | Br2 in CCl4, rtp
41
Alkene --> CO2 + H2O
Combustion | O2, heat
42
Benzene --> Cyclohexane
Reduction | H2, Ni, high temp and pressure
43
1 distinguishing test for phenol
neutral FeCl3 --> violet colouration | also can add Br2 aq --> tribromophenol is white ppt
44
Amine --> N-alkylated amine
NS | Limiting RX in ethanol, heat in sealed tube
45
Amine --> Amide
Condensation | RCOCl, rtp
46
Distinguish amines, amides, ammonium salts
Add NaOH Amine--> no reaction (unless storng prolonged) Amide --> NH3 (basic hydrolysis) Ammonium salts --> NH3 (acid-base)
47
Amine --> Ammonium salt
Acid-base | Add acid
48
Nitrobenzene --> Phenylamine
Reduction | Sn, conc HCl, heat, followed by NaOH
49
Amide --> Amine
Reduction | LiAlH4 in dry ether
50
Phenylamine --> Tribromophenylamine
ES | Br2(aq) rtp
51
RCOCl distinguishing test | Observations?
AgNO3 | --> AgCl (white ppt) and HCl white steamy fumes

Chemistry (9 decks)

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