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Chemistry > Alkanes - Hydroxy Cpds > Flashcards

Alkanes - Hydroxy Cpds Flashcards

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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
Q

Alcohol –> Bromoalkane

A

Nucleophilic Substitution
PBr3/SOBr2
/ KBr(s), conc H2SO4, heat (to generate HBr)
/ dry HBr, heat

26
Q

Alcohol –> Chloroalkane

A

Nucleophilic Substitution
PCl5/PCl3/SOCl2 rtp
or HCl(g), anhydrous ZnCl2, heat

27
Q

Alcohol –> Iodoalkane

A

Nucleophilic Substitution
red P, I2, heat (to produce PI3)
/ KI, conc H2SO4, heat (to generate HI)
/ dry HI, heat

28
Q

Ethanol –> Methanoic acid/ COO-Na+

Observations?

A

Oxidation (Iodoform test)
I2 (aq), NaOH (aq), warm

Yellow ppt formed

29
Q

Alcohol –> Aldehyde

Observations?

A

Oxidation
of primary alcohol

K2Cr2O7 (aq), H2SO4 (aq), heat with immediate distillation

30
Q

Alcohol –> Carboxylic acid

Observations?

A

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
Q

Alcohol –> Ketone

Observations?

A

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
Q

Alcohol –> CO-Na+

A

Redox

Na (s)

33
Q

Aldehyde –> Alcohol

A

Reduction
LiAlH4 in dry ether/
NaBH4/
H2, Ni, heat

34
Q

Ketone –> Alcohol

A

Reduction

LiAlH4 in dry ether

35
Q

Alcohol –> Ester

Two methods

A

Condensation
- Esterification
RCOOH, conc H2SO4, heat

  • Acylation
    RCOCl, rtp
36
Q

Phenol –> Sodium phenoxide

A

Acid-base
NaOH (aq)
or Acid-metal/Reduction
Na (s)

37
Q

Phenol –> trinitrophenol

A

Electrophilic Substitution

conc HNO3, rtp

38
Q

Phenol –> mononitrophenol

A

Electrophilic Substitution

dil. HNO3, rtp

39
Q

Phenol –> tribromophenol

Observations?

A

Electrophilic Substitution
Br2(aq), rtp

Rapid decolourisation of orange Br2, white ppt formed

40
Q

Phenol –> monobromophenol

A

Electrophilic Substitution

Br2 in CCl4, rtp

41
Q

Alkene –> CO2 + H2O

A

Combustion

O2, heat

42
Q

Benzene –> Cyclohexane

A

Reduction

H2, Ni, high temp and pressure

43
Q

1 distinguishing test for phenol

A

neutral FeCl3 –> violet colouration

also can add Br2 aq –> tribromophenol is white ppt

44
Q

Amine –> N-alkylated amine

A

NS

Limiting RX in ethanol, heat in sealed tube

45
Q

Amine –> Amide

A

Condensation

RCOCl, rtp

46
Q

Distinguish amines, amides, ammonium salts

A

Add NaOH
Amine–> no reaction (unless storng prolonged)
Amide –> NH3 (basic hydrolysis)
Ammonium salts –> NH3 (acid-base)

47
Q

Amine –> Ammonium salt

A

Acid-base

Add acid

48
Q

Nitrobenzene –> Phenylamine

A

Reduction

Sn, conc HCl, heat, followed by NaOH

49
Q

Amide –> Amine

A

Reduction

LiAlH4 in dry ether

50
Q

Phenylamine –> Tribromophenylamine

A

ES

Br2(aq) rtp

51
Q

RCOCl distinguishing test

Observations?

A

AgNO3

–> AgCl (white ppt) and HCl white steamy fumes

Chemistry (9 decks)

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