Organic synthesis Flashcards

1
Q

Exam technique for answering synthesis questions?

6 steps?

A
  1. Identify functional groups
  2. Look for difference between start and end molecules of the pathway and deduce how they might have happened
  3. Identify reagents that will add or remove atoms/groups of atoms to account for the differences
  4. Identify conditions for said reagents
  5. Use nature of reagent eg: nucleophile to decide on type of mechanism/reaction
  6. Don’t forget other products of reactions
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2
Q

Give the reagent needed to form an alkane from an alkene

A

H2

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3
Q

Give the reagent needed to form a haloalkane from an alkane

A

A halogen (X2)

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4
Q

Give the conditions needed to form an alkane from an alkene

2

A

Over Nickel catalyst

At 200*C

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5
Q

Give the conditions needed to form a haloalkane from an alkane
1

A

UV light

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6
Q

Give the reagent needed to form a haloalkane from an alkene?

A

Halogen halide (HX)

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7
Q

Give the conditions needed to form a haloalkane from an alkene?
1

A

Room temperature

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8
Q

Name the type of reaction to form a haloalkane from an akene

A

Nucleophilic Addition

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9
Q

Name the type of reaction to form a haloalkane from an alkane

A

Free Radical Substitution

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10
Q

Name the type of reaction to form an alkane from an alkene

A

Free Radical/Catalytic Addition

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11
Q

Give the reagent needed to form an amine from a haloalkane

A

Conc. NH3

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12
Q

Give the conditions needed to form an amine from a haloalkane
2

A

Heat

in a sealed tube

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13
Q

Name the type of reaction to form an amine from a haloalkane

A

Nucleophilic Substitution

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14
Q

Give the reagent needed to form a nitrile from a haloalkane

A

KCN

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15
Q

Give the conditions needed to form a nitrile from a haloalkane
3

A

Ethanolic solution
Reflux
Heat

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16
Q

Name the type of reaction to from a nitrile from a haloalkane

A

Nucleophilic Substitution

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17
Q

Give the reagent needed to form an amide from an amine

2

A

Acyl chloride or acid anhydride

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18
Q

Give the conditions needed to form an amide from an amine

1

A

Reflux

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19
Q

Name the type of reaction to form an amide from an amine

A

Acylation

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20
Q

Give the reagent needed to form an amine from a nitrile

A

H2

or LiAlH4

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21
Q

Give the conditions needed to form an amine from a nitrile

A

Nickel catalyst

200*C

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22
Q

Name the type of reaction to form an amine from a nitrile

A

Reduction / Electrophilic addition

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23
Q

Give the reagent needed to form an alcohol from a haloalkane

A

NaOH (aq)

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24
Q

Give the conditions needed to form an alcohol from a haloalkane
2

A

Reflux, warm

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25
Q

Name the type of reaction to from an alcohol from a haloalkane

A

Nucleophilic Substitution

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26
Q

Give the reagent needed to form an alkene from a haloalkane

A

Conc. KOH

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27
Q

Give the conditions needed to form an alkene from a haloalkane
2

A

Hot

Ethanolic

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28
Q

Name the type of reaction to form an alkene from a haloalkane

A

Elimination

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29
Q

Give the reagent needed to form an alkene from an alcohol

A

Conc. H2SO4

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30
Q

Give the conditions needed to form an alkene from an alcohol

2

A

Reflux, 180*C

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31
Q

Name the type of reaction to form an alkene from an alcohol

A

Elimination

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32
Q

Give the reagent needed to form an alcohol from an alkene

A

Conc, H3PO4

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33
Q

Give the conditions needed to form an alcohol from an alkene

3

A
Steam
High temp (300*C)
High pressure (60 atm)
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34
Q

Name the type of reaction to form an alcohol from an alkene

A

Electrophilic Addition

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35
Q

Give the reagent/conditions needed to form an alkyl hydrogensulphate from an alkene

A

Conc, H2SO4

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36
Q

Name the type of reaction to form an alkyl hydrogensulphate from an alkene

A

Addition

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37
Q

Give the reagent/conditions needed to form an alcohol from an alkyl hydrogensulphate

A

H2O

Warm

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38
Q

Give the reagent needed to form an aldehyde from a primary alcohol

A

K2Cr2O7

39
Q

Give the conditions needed to form an aldehyde from a primary alcohol
3
distill or reflux?

A

H+ so need H2SO4
Heat
Distill

40
Q

Name the type of reaction to form an aldehyde from a primary alcohol

A

Oxidation

41
Q
  1. Give the reagent needed to form a primary alcohol from an aldehyde
A

Aqueous NaBH4

42
Q
  1. Give the conditions needed to form a primary alcohol from an aldehyde
A

heat

ethanolic

43
Q

Name the type of reaction to form a primary alcohol from an aldehyde

A

Reduction

44
Q

Give the reagent needed to form a ketone from a secondary alcohol

A

K2Cr2O7

45
Q

Give the conditions to form a ketone from a secondary alcohol
3
distill or reflux?

A

H+ so need H2SO4
Heat
Reflux

46
Q

Name the type of reaction to form a ketone from a secondary alcohol

A

Oxidation

47
Q
  1. Give the reagent needed to form a secondary alcohol from a ketone
A

NaBH4

48
Q
  1. Give the conditions needed to form a primary alcohol from an aldehyde
A

dry ether

49
Q
  1. Give the conditions needed to form a secondary alcohol from a ketone
A

heat

ethanolic

50
Q
  1. Give the reagent needed to form a secondary alcohol from a ketone
A

LiAlH4

51
Q
  1. Give the conditions needed to form a secondary alcohol from a ketone
A

dry ether

52
Q

Give the reagent/conditions needed to form a 2-hydroxynitrile from a ketone

A

HCN

53
Q

Name the type of reaction to form a 2-hydroxynitrile from a ketone

A

Nucleophilic addition

54
Q

Give the reagent needed to form a carboxylic acid from an aldehyde
3 options

A
K2Cr2O7
or
Tollens reagent
or
Fehlings solution
55
Q

Give the conditions needed to form a carboxylic acid from an aldehyde
3

A

Heat
Reflux
H+ so needs H2SO4

56
Q

Name the type of reaction to form a carboxylic acid from an aldehyde

A

Oxidation

57
Q

Give the reagent needed to form an ester from a carboxylic acid

A

Alcohol

58
Q

Give the conditions needed to form an ester from a carboxylic acid

A

Conc H2SO4

59
Q

Name the type of reaction to form an ester from a carboxylic acid

A

Esterification

60
Q

Give the reagent needed to form a carboxylic acid from an ester
2 options

A

H+ or OH-

so acid eg: H2SO4 or an alcohol

61
Q

Give the conditions needed to form a carboxylic acid from an ester

A

Reflux

62
Q

Name the type of reaction to form a carboxylic acid from an ester

A

Hydrolysis

63
Q

Give the reagents needed to form an ester from an alcohol

3

A
Carboxylic acid
or
Acyl chloride
or
Acid anhydride
64
Q

Give the conditions needed to form an ester from an alcohol

A

Conc H2SO4

65
Q

Name the type of reaction to form an ester from an alcohol

A

Esterification

66
Q

Give the reagents needed to form an amide from an acyl chloride

A

NH3 or 1/2 amine

67
Q

Name the type of reaction to form an amide from an acyl chloride

A

nucleophilic substitution

68
Q

Give the reagents and conditions needed to form an ester from an acid anhydride

A

Alcohol

H+

69
Q

Name the type of reaction to form an ester from an acid anhydride

A

esterification

70
Q

Give the reagents needed to form a hydroxynitrile from an aldehyde

A

NaCN(aq) / H+(aq)

71
Q

name the type of reaction to form a hydroxynitrile from an aldehyde

A

Nucleophilic addition

72
Q

Give the reagents and conditions needed to form a carboxylic acid from an acyl chloride

A

warm water with H+ or OH-

73
Q

Give the conditions needed to form an acyl chloride from a carboxylic acid

A

SOCl2

74
Q

Give the reagent needed to form a carboxylic acid from a nitrile

A

Acid/ H+(aq)

75
Q

Name the type of reaction to form a carboxylic acid from a nitrile

A

Acid hydrolysis

76
Q

Give the reagent needed to form cyclohexane from benzene

A

H2

77
Q

Give the conditions needed to form cyclohexane from benzene

A

Nickel catalyst

150*C

78
Q

Name the reaction to form cyclohexane from benzene

A

Reduction

79
Q

give the reagents needed to form nitrobenzene from benzene

A

conc HNO3

conc H2SO4

80
Q

give the conditions needed to form nitrobenzene from benzene

A

50*C

81
Q

Name the reaction to form nitrobenzene from benzene

A

Electrophilic substitution

nitration

82
Q

Give the reagents and conditions needed to form phenylamine from nitrobenzene

A

NaOH
conc H2SO4
Sn catalyst

83
Q

Name the type of reaction to form pheylamine from nitrobenzene

A

Reduction

84
Q

Give the reagent needed to form N-phenylethanamide from phenylamine

A

Ethanoyl Chloride

85
Q

Name the type of reaction to form N-phenylethanamide from phenylamine

A

Acylation

86
Q

Give the reagents and conditions needed to form phenylethene from benzene

A

CH3CH2O

AlCl3 catalyst

87
Q

Name the type of reaction to form phenylethene from benzene

A

Electrophlic substitution
(friedel-crafts acylation)
then catalytic dehydrogenation

88
Q

Give the conditions needed to form polystyrene from phenylethene

A

Ziegler catalyst

89
Q

Name the reaction to form polystyrene from phenylethene

A

Polymerisation

90
Q

Give the reagents and conditions needed to form methylpheylketone from benzene

A

HCOCl
AlCl3 catalyst
40*C

91
Q

Name the type of reaction to form methylphenylketone from benzene

A
Electrophilic substitution
(friedel-crafts acylation)
92
Q

Give the reagents and conditions to form methylbenzene from benzene

A

RCl
AlCl3 catalyst
40*C

93
Q

Name the reaction to form methylbenzene from benzene

A
Electrophilic substitution 
(friedel-crafts alkylation)