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SYNTHESIS ROUTES Flashcards

1
Q

ALKENE → ALCOHOL

A

DIRECT HYDRATION

REAGENT: steam + H3PO4 catalyst
CONDITION: 300ºc + 60-70 atm

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2
Q

ALKENE → ALKANE

A

HYDROGENATION

REAGENT: H2 + Nickle catalyst
CONDITION: 150ºc

–> used in margarine manufacture

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3
Q

ALKENE → HALOALKANE

+ draw mechanism

A

ELECTROPHILIC ADDITION

REAGENT: Hydrogen Halide (H=+) (X=-)
CONDITION: room temp

  • mechanism
    arrow from C=C to H, arrow from H to BR
    arrow from BR- to +carbon
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4
Q

ALCOHOL → ALKENE

A

ELIMINATION (removes water)

REAGENT: CONC. H3PO4 catalyst
CONDITION: REFLUX

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5
Q

ALCOHOL → ESTER (+H2O)

A

-removes water

REAGENT: carboxylic acid + CONC H2SO4 catatlyst
CONDITION: reflux

-used in flavourings, solvents, plasticisers

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6
Q

ALKENE + STEAM (+H3PO4)

A

ALCOHOL

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7
Q

ALKENE + H2 (+Ni)

A

ALKANE

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8
Q

ALKENE +HYDROGEN HALIDE

A

HALOALKANE

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9
Q

ALCOHOL (+ H3PO4 + REFLUX)

A

ALKENE

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10
Q

ALCOHOL + CARBOXYLIC ACID

A

ESTER + H2O

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11
Q

ALKENE → ALCOHOL TYPE OF REACTION

A

DIRECT HYDRATION

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12
Q

ALKENE → ALKANE TYPE OF REACTION

A

HYDROGENATION

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13
Q

ALKENE → HALOALKANE TYPE OF REACTION

A

ELECTROPHILIC ADDITION

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14
Q

ALCOHOL → ALKENE TYPE OF REACTION

A

ELIMINATION

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15
Q

ALCOHOL → HALOALKANE

A

REAGENT: sodium halide + H2SO4
CONDITION: reflux

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16
Q

ALCOHOL + SODIUM HALIDE (+H2SO4)

A

HALOALKANE

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17
Q

ALCOHOL → ALDEHYDE

A

REAGENT: 1º alcohol
CONDITIONS: distill, getnle heat + acidified K2Cr2O7

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18
Q

1º ALCOHOL DISTILLED + HEATED GENTLY

A

ALDEHYDE

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19
Q

ALCOHOL → ALDEHYDE TYPE OF REACTION

A

OXIDATION

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20
Q

ALCOHOL → ALDEHYDE OBSERVATION

A

COLOUR CHANGE

ORANGE → GREEN

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21
Q

ALCOHOL → KETONE

A

REAGENT: 2º alcohol
CONDITION: reflux w/ acidified K2Cr2O7

*in equation w/ [O] remeber it is [O] per alcohol group

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22
Q

ALCOHOL → KETONE TYPE OF REACTION

A

OXIDATION

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23
Q

ALCOHOL → KETONE OBSERVATION

A

COLOUR CHANGE

ORANGE → GREEN

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24
Q

ALDEHYDE → CARBOXYLIC ACID

A

oxidation

REAGENT: aldehyde + acidified K2CR2O7
CONDITION: reflux

*in equation w/ [O] remeber it is 1[O] per aldehyde group

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25
Q

ALDEHYDE + REFLUX W/ H+/K2CR2O7

A

CARBOXYLIC ACID

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26
Q

ALDEHYDE → CARBOXYLIC ACID TYPE OF REACTION

A

OXIDATION

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27
Q

ALCOHOL → CARBOXYLIC ACID

A

REGENT: 1º alcohol + acidified K2CR2O7
CONDITION: reflux

*in equation w/ [O] remember it is 2[O] per alcohol group

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28
Q

1º ALCOHOL + REFLUX W/ H+/K2CR2O7

A

CARBOXYLIC ACID

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29
Q

ALDEHYDE → 1º ALCOHOL

+ mech

A

NUCLEOPHILIC ADDITION

REAGENT: warm, aq NaBH4 (:H-)

*mechanism:
arrow on C=O from C→O, arrow from :H- to C
arrow from :O- to H on H-O-H

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30
Q

ALDEHYDE + WARM NaBH4 (aq)

A

1º ALCOHOL

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31
Q

ALDEHYDE → 1º ALCOHOL TYPE OF REACTION

A

NUCLEOPHILIC ADDITION

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32
Q

KETONE → 2º ALCOHOL

+ mech

A

NUCLEOPHILIC ADDITION

REAGENT: warm, aq NaBH4 (:H-)

*mechanism:
arrow on C=O from C→O, arrow from :H- to C
arrow from :O- to H on H-O-H

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33
Q

KETONE + WARM NaBH4 (aq)

A

2º ALCOHOL

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34
Q

KETONE → 2º ALCOHOL TYPE OF REACTION

A

NUCLEOPHILIC ADDITION

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35
Q

CARBONYL → HYDROXYNITRILE

A

NUCLEOPHILIC ADDITION CN- = nucleophile

REAGENT: HCN made in situ (NaCN + H2SO4) .:. NaCN/H+

CONDITION: Reflux in alkaline condition

*mechanism:
arrow from C→O (C=O), arrow from -:CN to C
arrow from :O- →H+

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36
Q

CARBONYL → HYDROXYNITRILE TYPE OF REACTION

A

NUCLEOPHILIC ADDITION

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37
Q

CARBONYL + NaCN/H+

A

HYDROXYNITRILE

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38
Q

CARBOXYLIC ACID → ESTER

A

REAGENT: ALCOHOL + CONC H2SO4
CONDITION: REFLUX

produces H2O

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39
Q

CARBOXYLIC ACID + ALCOHOL (+ CONC H2SO4)

A

ESTER

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40
Q

ACYL CHLORIDE → ESTER

A

REAGENT: ACYL CHLORIDE + ALCOHOL
CONDITION: DRY REFLUX

produces HCL

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41
Q

ACYL CHLORIDE + ALCOHOL

A

ESTER + HCl

42
Q

ALCOHOL + ACID ANHYDRIDE

A

ESTER + COOH

43
Q

ALCOHOL → ESTER (+COOH)

A

REAGENT: ACID ANHYDRIDE + ALCOHOL
CONDITION: DRY REFLUX

H removed from -OH
ester link on acid anhydride broken and RCOO removed
these form the carboxylic acid

44
Q

ESTER → CARBOXYLIC ACID + ALCOHOL

A

HYDROLYSIS

REAGENT: DILUTE ACID (HCl) - CATALYST
CONDITION: REFLUX

45
Q

ESTER + DILUTE ACID (eg HCl)

A

CARBOXYLIC ACID + ALCOHOL

46
Q

ESTER → CARBOXYLIC ACID + ALCOHOL TYPE OF REACTION

A

HYDROLYSIS

47
Q

ESTER → CARBOXYLATE SALT + ALCOHOL

A

REAGENT: DILUTE ALKALI (NaOH) - CATALYST
CONDITION: REFLUX

48
Q

ESTER + DILUTE ALKALI (eg NaOH)

A

CARBOXYLATE SALE + ALCOHOL

49
Q

ACYL CHLORIDE → CARBOXYLIC ACID + HCL

A

COLD WATER

-produces HCl as a dense white fume

50
Q

ACYL CHLORIDE + COLD WATER

A

CARBOXYLIC ACID + HCL

51
Q

ACYL CHLORIDE → CARBOXYLIC ACID + HCL OBSERVATION

A

DENSE WHITE FUME OF HCl

52
Q

ACYL CHLORIDE → 1º AMIDE

+mechanism

A

REAGENT: NH3
CONDITION: ROOM TEMP

*mechanism:
arrow from C→O (C=O), arrow from :NH3→C
arrow from -:O→C, arrow from C→CL
forms RC(O)NH3 + -:Cl
53
Q

CARBOXYLIC ACID → ACID ANHYDRIDE

A

REAGENT: 2xCARBOXYLIC ACID

forms acid anhydride + H2O

54
Q

CARBOXYLIC ACID + CARBOXYLIC ACID

A

ACID ANHYDRIDE + H2O

55
Q

HYDROXYNITRILE → AMINE

56
Q

NITRILE → AMINE

57
Q

BENZENE → NITROBENZENE

+ MECH

A

REAGENT: CONC HNO3 + CONC H2SO4
CONDITION: REFLUX @ 50ºC

mechanism:
arrow from benzene ring to +NO2
arrow from H to positive benzene ring
forms nitrobenzene + H+

58
Q

BENZENE → NITROBENZENE TYPE OF REACTION

A

ELECTROPHILIC SUBSTITUTION

59
Q

WHAT IS THE ELECTROPHILE IN BENZENE → NITROBENZENE

60
Q

HOW IS THE ELECTROPHILE GENERATED IN BENZENE → NITROBENZENE

A

CONC H2SO4 + CONC HNO3

H2SO4 + HNO3 → HSO4(-) + NO2(+) + H2O

61
Q

BENZENE → NITROBENZENE EQUATION

A

C6H6 + HNO3 → C6H5NO2 + H2O

62
Q

BENZENE → HALOBENZENE (+ hydrogen halide)

+ MECH

A

REAGENT: HALOGEN + HALOGEN CARRIER
e.g, halogen carrier: FeCl3 // AlCl3
CONDITION: REFLUX

mechanism:
arrow from benzene ring to +Cl
arrow from H to positive benzene ring
forms halobenzene + H+

63
Q

BENZENE + H2SO4 + HNO3

A

NITROBENZENE + H2O

64
Q

BENZENE → HALOBENZENE EQUATION

A

C6H6 + Cl2 → C6H5Cl + HCL

65
Q

HOW IS THE HALIDE GENERATED IN BENZENE → HALOBENZENE BY THE HALOGEN CARRIER.

HOW IS THE HALOGEN CARRIER REGENERATED

E.G, AlCl3 + Cl2

A

Cl2 + AlCl3 → AlCl4- + Cl+

regenerated by reacting with the H+ formed
AlCl4- + H+ → AlCl3 + HCl

66
Q

PHENOL → SODIUM PHENOXIDE

A

NEUTRILISATION

REAGENT: NaOH (aq)

EQUATION:
C6H5OH + NaOH → C6H5O-Na+ + H2O

67
Q

PHENOL + NaOH (aq)

A

SODIUM PHENOXIDE

68
Q

NITROBENZENE → PHENYLAMINE

A

Sn (tin) + CONC HCl

69
Q

PHENYLAMINE → 2, 4, 6 TRIBROMO PHENYLAMINE

A

3x Br2

  • also forms 3x HBr
70
Q

BENZENE → PHENYLETHANONE

A

ETHANOYL CHLORIDE + AlCl3

benzene w/ a KETONE group

71
Q

BENZENE → ALKYLBENZENE

+ mechanism (e.g, C2H5Cl)

A

REAGENT: haloalkane + anhydrous AlCl3
CONDITION: room temp + dry inert solvent

EQUATION:
C6H6 + C2H5Cl → C6H5C2H5 + HCl

mechanism:
arrow from benzene ring → +C2H5
arrow from H → positive benzene ring
forms alkyl benzene + H+

72
Q

WHAT IS THE ELECTROPHILE IN BENZENE → ALKYLBENZENE

A

+ alkyl group

e.g, +C2H5

73
Q

HOW IS THE ELECTROPHILE GENERATED IN BENZENE → ALKYLBENZENE

A

C2H5Cl + AlCl3 → (+)C2H5 + AlCl4(-)

74
Q

PHENOL → 2 or 4 NITROPHENOL

A

REAGENT: DILUTE HNO3

EQUATION
C6H5OH + HNO3 → C6H5(OH)(NO2) + H2O

75
Q

NITROBENZENE + Sn + CON HCl

A

PHENYLAMINE

76
Q

BENZENE + HALOALKANE = anhydrous AlCl3

A

ALKYLBENZENE

77
Q

PHENOL + DILUTE HNO3

A

2 or 4 NITROPHENOL

78
Q

PHENOL → 2,4,6-TRIBROMOPHENOL

A

REAGENT: BROMINE WATER
CONDITION: ROOM TEMP - NO CATALYST

79
Q

PHENOL → 2,4,6-TRIBROMOPHENOL TYPE OF REACTION

A

ELECTROPHILIC SUBSTITUTION

80
Q

PHENOL → 2,4,6-TRIBROMOPHENOL OBSERVATION

A

COLOUR CHANGE
ORANGE TO COLOURLESS

WHITE PPT FORMS

81
Q

PHENOL + 3x HBr

A

2,4,6-TRIBROMOPHENOL

82
Q

HALOALKANE → NITRILE

A

CN- + EHTANOL

83
Q

HALOALKANE + CN- + ETHANOL

84
Q

CARBOXYLIC ACID → ACYL CHLORIDE

A

REAGENT; SOCl2 (thionyl chloride)
CONDITION: DRY (to stop other reaction)

forms acyl chloride + SO2 + HCl

85
Q

CARBOXYLIC ACID → ACYL CHLORIDE TYPE OF REACTION

A

CHLORINATION

86
Q

WHY DOES THE CARBOXYLIC ACID → ACYL CHLORIDE NEED TO BE DRY

A

TO STOP OTHER REACTIONS TAKING PLACE

87
Q

CARBOXYLIC ACID + SOCl2

A

ACYL CHLORIDE

88
Q

NITRILE →CARBOXYLIC ACID

A

REFLUX W/ DILUTE HCl
→ H2O, HCL, HEAT

EQUATION:
R-CH2-CN + 2H2O + HCl → R-CH2-COOH + NH4Cl

89
Q

NITRILE →CARBOXYLIC ACID TYPE OF REACTION

A

HYDROLYSIS

90
Q

NITRILE REFLUX W/ DILUTE HCl

A

CARBOXYLIC ACID

91
Q

HALOALKANE → ALCOHOL

A

WARM NaOH (aq)

92
Q

HALOALKANE + WARM NaOH (aq)

93
Q

HALOALKANE → 1º AMINE

A

NUCLEOPHILIC SUBSTITUTION

REAGENT: EHTANOLIC AMMONIA

EQAUTION:
2 NH3 + CH3CH2Br →CH3CH3NH2 + NH4Br

94
Q

HALOALKANE → AMINE TYPE OF REACTION

A

NUCLEOPHILIC SUBSTITUTION

95
Q

ACYL CHLORIDE → 2º AMINE (+ HCl)

A

REAGENT: 1º AMINE

Cl comes off acyl chloride
H comes of NH2 of the 1º amine
these form HCl

96
Q

ACYL CHLORIDE + 1º AMINE

A

2º AMINE + HCl

97
Q

HALOALKANE + ETHANOLIC AMMONIA

98
Q

ALKANE → HALOALKANE

A

HALOGEN + UV

99
Q

ALKANE → HALOALKANE FREE RADICAL SUBSTITUTION STEPS

e.g, using Cl2 + CH4

A

INITIATION

  • radicals made
  • UV
  • e.g, Cl2 → 2Cl•

PROPAGATION
- radicals used + regenerated
- e.g, Cl• + CH4 → CH3• + HCL
CH3• + Cl2 → CH3Cl + Cl•

TERMINATION
- radicals removed
- e.g, Cl• + Cl• → Cl2
CH3• + Cl• → CH3Cl

100
Q

HOW DOES UV SPLIT THE HALOGEN IN FREE RADICAL SUBSTITUTION

A

HOMOLYTIC FISSION

OCR A CHEM (9 decks)

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