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Chemistry > ORGANIC REAGENTS > Flashcards

ORGANIC REAGENTS Flashcards

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1
Q

Alkane to Haloalkane

A 
UV light or heat
gaseous halogen (Cl2)

free radical substitution
homolytic fission

Cl₂ ➜ 2Cl

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2
Q

Alkane to Combustion Products

A 
Oxygen 2 Heat

Combustion/incomplete

CₓH₂ₓ₊₂ + O₂ ➜ CO₂ + H₂O

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3
Q

Alkene to Alkane

A 
Nickel catalyst, H₂ gas

Hydrogenation

C=C + H₂ ➜ C-C

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4
Q

Alkene to Haloalkane (one halogen)

A 
Hydrogen halides, room temp

electrophilic addition
heterolytic fission
carbocation

CH₂=CH₂ + HCL ➜ CH₃CH₂Cl

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5
Q

Alkene to Haloalkane (dihalo-)

A 
aqueous halogen, room temp

Electrophilic addition
Heterolytic fission
Carbocation

CH₂=CH₂ + Cl₂ ➜ CH₃CHCl₂

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6
Q

Alkene to Alcohol

A 
phosphoric acid catalyst, steam

Hydration

CH₂ = CH₂ + H₂O ⇌ CH₃CH₂OH

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7
Q

Alkene to Polymer

A 
H2 gas and Ni catalyst

Free radical addition

nCH₂ = CH₂ ➜ [CH₂-CH₂]ₙ & Ra* + CH₂ = CH₂ ➜ RaCH₂CH₂ *

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8
Q

Haloalkane

Haloalkane to Alcohol (alkali)

A 
dilute NaOH or KOH

Nucleophilic sub
hydrolysis
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9
Q

Haloalkane

Haloalkane to Alcohol (water)

A 
heat warmly, use H₂O

nucleophilic sub
hydrolysis
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10
Q

Haloalkane

Haloalkane to Amine

A 
heat with NH3 in ethanol

nucleophilic sub
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11
Q

Haloalkane

Haloalkane to Nitrile

A 
warm NaCN/KCN, dilute ethanol (CN- + HCl)

Nucleophilic sub
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12
Q

Alcohols

Alcohol to Combustion Products

A 
oxygen 2 heat

combustion/incomplete

CH₃OH + 3/2O₂ ➜ CO₂ + 2H₂O

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13
Q

Alcohols

Alcohol to Aldehyde

A 
Acidified (H₂SO₄) Potassium Dichromate (K₂Cr₂O₇) to be used to distill at temp to collect aldehyde

primary alcohol

CH₃CH₂OH + [O] ➜ CH₃CHO + H₂O

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14
Q

Alcohols

Alcohol to Ketone

A 
Heat under reflux + H2SO4 and potassium dichromate

secondary alcohol

CH₃CH(OH)CH₃ + [O] ➜ CH₃COCH₃ + H₂O

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15
Q

Alcohols

Alcohol to Carboxylic Acid

A 
heat under reflux + acidified potassium dichromate

Primary alcohol

CH₃CH₂OH + 2[O] ➜ CH₃COOH + H₂O

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16
Q

Alcohols

Alcohol to Alkene

A 
Heat + conc H2SO4

Any alcohol
Dehydration

CH₃CH₂OH –(H₂SO₄)–> C=C

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17
Q

Alcohols

Alcohol to Haloalkane

A 
sodium halide + H₂SO₄

Any alcohol
halide substitution

CH₃CH₂OH + NaBr ➜ CH₃CH₂Br + Na⁺

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18
Q

Alcohols

Alcohol to ester

A 
heat with conc H₂SO₄ and carboxylic acid OR ACID ANYHYDRIDE

condensation - esterfication

R - OH + H-O - C = O - R
reflux

OH from carboxylic acid and H from alcohol make H₂O

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19
Q

Carbonyls

Aldehyde to carboxylic acid

A 
H₂SO₄ + potassium dichromate and heat under reflux

Oxidation
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20
Q

Carbonyls

Aldehyde or ketone to alcohol

A 
NaBh₄ (H- attacks C), aq or alcoholic solution

Nucleophilic addition - reduction
1°or 2° alcohol
21
Q

Carbonyls

Aldehyde or ketone to hydroxynitrile

A 
HCN [i.e. NaCN(aq)/H+(aq)]

nucleophilic addition HCN
22
Q

Carboxylic acids and derivatives

Carboxylic to ester

A

Alcohol + carboxylic acid + conc H₂SO₄
condensation

23
Q

Carboxylic acids and derivatives

Carboxylic to salts

A

Any metal in solution

neutralisation

24
Q

Carboxylic acids and derivatives

Carboxylic to Acyl chloride

A

thionyl chloride SOCL2
acylation

25
Q

Carboxylic acids and derivatives

Acid Anhydride to ester

A

alcohol + acid an = ester
condensation

26
Q

Carboxylic acids and derivatives

Acyl chloride to Ester

A

alcohol at room temp
condensation

27
Q

Carboxylic acids and derivatives

Acyl chloride to Amide

A

conc ammonia (prim) or primary amine(sec)
condensation

28
Q

Carboxylic acids and derivatives

Ester to carboxylic acid and Alcohol

A

dilute HCL or H2SO4 and heat
acid hydrolysis

29
Q

Carboxylic acids and derivatives

Ester to carboxylate and Alcohol

A

NaOH and heat
alkaline hydrolysis

30
Q

Amines, Amino acids and Amides

Amine to salt

A

HCl at rtp
neutralisation

31
Q

Amines, Amino acids and Amides

Amino acid to Ester

A

Alcohol with conc H₂SO₄ under reflux or acyl chloride at rtp
condensation

32
Q

Amines, Amino acids and Amides

Amino acid to salt

A

HCl at rtp
neutralisation

33
Q

Amines, Amino acids and Amides

Amino acid to salt

A

NaOH at rtp
neutralisation

34
Q

Nitriles

Hydroxynitrile to Amine

A

(H2 gas and Ni catalyst)
Reduction

35
Q

Nitriles

Nitrile to Amine

A

LiAlH₄, H2 gas and Ni catalyst
Reduction

36
Q

Nitriles

Hydroxynitrile to Carboxylic acid

A

dilute HCl and H2SO4 and heat
Oxidation, acid hydrolysis

37
Q

Condensation Polymers

Polyester to Carboxylic acid & Alcohol

A

dilute HCl under reflux
acid hydrolysis

38
Q

Condensation Polymers

Polyester to Carboxylate & Alcohol

A

dilute NaOH under reflux
alkaline hydrolysis

39
Q

Condensation Polymers

Polyamide to Carboxylic acid & Alcohol

A

dilute HCl + reflux
acid hydrolysis

40
Q

Condensation Polymers

Polyamide to Carboxylate & Alcohol

A

dilute NaOH with heat
alkaline hydrolysis

41
Q

Aromatic

Benzene to Nitrobenezene

A

conc H₂SO₄ & conc HNO₃ at reflux
Electrophilic substitution

HNO3 + H2SO4 ➜ NO2⁺ + HSO4⁻ + H2O

42
Q

Aromatic

Benzene to Halobenzene

A

Bromobenzene = Br2 & FeBr3 and Chlorobenzene = Cl2 and AlCl3
Electrophilic substitution

Br2 + FeBr3 ➜ Br⁺ + Febr4⁻

43
Q

Aromatic

Benzene to Alkylbenzene

A

AlCl₃ & under reflux
Electrophilic substitution

  • alkylation

AlCl3 + CH3Cl ➜ AlCl4⁻ + CH3⁺

44
Q

Aromatic

Benzene to Acylbenzene

A

AlCl₃ and CH3COCl
Electrophilic substitution

  • acylation
  • carbo acid ion attached to benzene and then becomes ketone

AlCl3 + CH3COCl ➜ AlCl4⁻ + CH3CO⁺

45
Q

Aromatic

Benzene to Cyclohexane

A

Nickel catalyst, H₂ gas
Hydrogenation

46
Q

Aromatic

Nitrobenzene to Phenylamine

A

Sn and conc HCl and heated under reflux, then NaOH is used to neutralise
Reduction then Neutralisation

47
Q

Aromatic

Phenol to Bromophenol

A

2,4 directing!
Electrophilic substitution

bromine water - Br2

48
Q

Aromatic

Phenol to Nitrophenol

A

2,4 directing
Electrophilic substitution

Dilute HNO3

49
Q

Aromatic

Phenol to Phenoxide

A

Acid & Base = add water or Neutralisation = add metal

Chemistry (9 decks)

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