SYNTHESIS ROUTES Flashcards
1
Q
ALKENE → ALCOHOL
A
DIRECT HYDRATION
REAGENT: steam + H3PO4 catalyst
CONDITION: 300ºc + 60-70 atm
2
Q
ALKENE → ALKANE
A
HYDROGENATION
REAGENT: H2 + Nickle catalyst
CONDITION: 150ºc
–> used in margarine manufacture
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
4
Q
ALCOHOL → ALKENE
A
ELIMINATION (removes water)
REAGENT: CONC. H3PO4 catalyst
CONDITION: REFLUX
5
Q
ALCOHOL → ESTER (+H2O)
A
-removes water
REAGENT: carboxylic acid + CONC H2SO4 catatlyst
CONDITION: reflux
-used in flavourings, solvents, plasticisers
6
Q
ALKENE + STEAM (+H3PO4)
A
ALCOHOL
7
Q
ALKENE + H2 (+Ni)
A
ALKANE
8
Q
ALKENE +HYDROGEN HALIDE
A
HALOALKANE
9
Q
ALCOHOL (+ H3PO4 + REFLUX)
A
ALKENE
10
Q
ALCOHOL + CARBOXYLIC ACID
A
ESTER + H2O
11
Q
ALKENE → ALCOHOL TYPE OF REACTION
A
DIRECT HYDRATION
12
Q
ALKENE → ALKANE TYPE OF REACTION
A
HYDROGENATION
13
Q
ALKENE → HALOALKANE TYPE OF REACTION
A
ELECTROPHILIC ADDITION
14
Q
ALCOHOL → ALKENE TYPE OF REACTION
A
ELIMINATION
15
Q
ALCOHOL → HALOALKANE
A
REAGENT: sodium halide + H2SO4
CONDITION: reflux
16
Q
ALCOHOL + SODIUM HALIDE (+H2SO4)
A
HALOALKANE
17
Q
ALCOHOL → ALDEHYDE
A
REAGENT: 1º alcohol
CONDITIONS: distill, getnle heat + acidified K2Cr2O7
18
Q
1º ALCOHOL DISTILLED + HEATED GENTLY
A
ALDEHYDE
19
Q
ALCOHOL → ALDEHYDE TYPE OF REACTION
A
OXIDATION
20
Q
ALCOHOL → ALDEHYDE OBSERVATION
A
COLOUR CHANGE
ORANGE → GREEN
21
Q
ALCOHOL → KETONE
A
REAGENT: 2º alcohol
CONDITION: reflux w/ acidified K2Cr2O7
*in equation w/ [O] remeber it is [O] per alcohol group
22
Q
ALCOHOL → KETONE TYPE OF REACTION
A
OXIDATION
23
Q
ALCOHOL → KETONE OBSERVATION
A
COLOUR CHANGE
ORANGE → GREEN
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
25
ALDEHYDE + REFLUX W/ H+/K2CR2O7
CARBOXYLIC ACID
26
ALDEHYDE → CARBOXYLIC ACID TYPE OF REACTION
OXIDATION
27
ALCOHOL → CARBOXYLIC ACID
REGENT: 1º alcohol + acidified K2CR2O7
CONDITION: reflux
*in equation w/ [O] remember it is 2[O] per alcohol group
28
1º ALCOHOL + REFLUX W/ H+/K2CR2O7
CARBOXYLIC ACID
29
ALDEHYDE → 1º ALCOHOL
+ mech
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
30
ALDEHYDE + WARM NaBH4 (aq)
1º ALCOHOL
31
ALDEHYDE → 1º ALCOHOL TYPE OF REACTION
NUCLEOPHILIC ADDITION
32
KETONE → 2º ALCOHOL
+ mech
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
33
KETONE + WARM NaBH4 (aq)
2º ALCOHOL
34
KETONE → 2º ALCOHOL TYPE OF REACTION
NUCLEOPHILIC ADDITION
35
CARBONYL → HYDROXYNITRILE
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+
36
CARBONYL → HYDROXYNITRILE TYPE OF REACTION
NUCLEOPHILIC ADDITION
37
CARBONYL + NaCN/H+
HYDROXYNITRILE
38
CARBOXYLIC ACID → ESTER
REAGENT: ALCOHOL + CONC H2SO4
CONDITION: REFLUX
produces H2O
39
CARBOXYLIC ACID + ALCOHOL (+ CONC H2SO4)
ESTER
40
ACYL CHLORIDE → ESTER
REAGENT: ACYL CHLORIDE + ALCOHOL
CONDITION: DRY REFLUX
produces HCL
41
ACYL CHLORIDE + ALCOHOL
ESTER + HCl
42
ALCOHOL + ACID ANHYDRIDE
ESTER + COOH
43
ALCOHOL → ESTER (+COOH)
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
ESTER → CARBOXYLIC ACID + ALCOHOL
HYDROLYSIS
REAGENT: DILUTE ACID (HCl) - CATALYST
CONDITION: REFLUX
45
ESTER + DILUTE ACID (eg HCl)
CARBOXYLIC ACID + ALCOHOL
46
ESTER → CARBOXYLIC ACID + ALCOHOL TYPE OF REACTION
HYDROLYSIS
47
ESTER → CARBOXYLATE SALT + ALCOHOL
REAGENT: DILUTE ALKALI (NaOH) - CATALYST
CONDITION: REFLUX
48
ESTER + DILUTE ALKALI (eg NaOH)
CARBOXYLATE SALE + ALCOHOL
49
ACYL CHLORIDE → CARBOXYLIC ACID + HCL
COLD WATER
-produces HCl as a dense white fume
50
ACYL CHLORIDE + COLD WATER
CARBOXYLIC ACID + HCL
51
ACYL CHLORIDE → CARBOXYLIC ACID + HCL OBSERVATION
DENSE WHITE FUME OF HCl
52
ACYL CHLORIDE → 1º AMIDE
+mechanism
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
CARBOXYLIC ACID → ACID ANHYDRIDE
REAGENT: 2xCARBOXYLIC ACID
forms acid anhydride + H2O
54
CARBOXYLIC ACID + CARBOXYLIC ACID
ACID ANHYDRIDE + H2O
55
HYDROXYNITRILE → AMINE
H2/Ni
56
NITRILE → AMINE
H2/Ni
57
BENZENE → NITROBENZENE
+ MECH
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
BENZENE → NITROBENZENE TYPE OF REACTION
ELECTROPHILIC SUBSTITUTION
59
WHAT IS THE ELECTROPHILE IN BENZENE → NITROBENZENE
NO2+
60
HOW IS THE ELECTROPHILE GENERATED IN BENZENE → NITROBENZENE
CONC H2SO4 + CONC HNO3
H2SO4 + HNO3 → HSO4(-) + NO2(+) + H2O
61
BENZENE → NITROBENZENE EQUATION
C6H6 + HNO3 → C6H5NO2 + H2O
62
BENZENE → HALOBENZENE (+ hydrogen halide)
+ MECH
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
BENZENE + H2SO4 + HNO3
NITROBENZENE + H2O
64
BENZENE → HALOBENZENE EQUATION
C6H6 + Cl2 → C6H5Cl + HCL
65
HOW IS THE HALIDE GENERATED IN BENZENE → HALOBENZENE BY THE HALOGEN CARRIER.
HOW IS THE HALOGEN CARRIER REGENERATED
E.G, AlCl3 + Cl2
Cl2 + AlCl3 → AlCl4- + Cl+
regenerated by reacting with the H+ formed
AlCl4- + H+ → AlCl3 + HCl
66
PHENOL → SODIUM PHENOXIDE
NEUTRILISATION
REAGENT: NaOH (aq)
EQUATION:
C6H5OH + NaOH → C6H5O-Na+ + H2O
67
PHENOL + NaOH (aq)
SODIUM PHENOXIDE
68
NITROBENZENE → PHENYLAMINE
Sn (tin) + CONC HCl
69
PHENYLAMINE → 2, 4, 6 TRIBROMO PHENYLAMINE
3x Br2
- also forms 3x HBr
70
BENZENE → PHENYLETHANONE
ETHANOYL CHLORIDE + AlCl3
| benzene w/ a KETONE group
71
BENZENE → ALKYLBENZENE
+ mechanism (e.g, C2H5Cl)
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
WHAT IS THE ELECTROPHILE IN BENZENE → ALKYLBENZENE
+ alkyl group
e.g, +C2H5
73
HOW IS THE ELECTROPHILE GENERATED IN BENZENE → ALKYLBENZENE
C2H5Cl + AlCl3 → (+)C2H5 + AlCl4(-)
74
PHENOL → 2 or 4 NITROPHENOL
REAGENT: DILUTE HNO3
EQUATION
C6H5OH + HNO3 → C6H5(OH)(NO2) + H2O
75
NITROBENZENE + Sn + CON HCl
PHENYLAMINE
76
BENZENE + HALOALKANE = anhydrous AlCl3
ALKYLBENZENE
77
PHENOL + DILUTE HNO3
2 or 4 NITROPHENOL
78
PHENOL → 2,4,6-TRIBROMOPHENOL
REAGENT: BROMINE WATER
CONDITION: ROOM TEMP - NO CATALYST
79
PHENOL → 2,4,6-TRIBROMOPHENOL TYPE OF REACTION
ELECTROPHILIC SUBSTITUTION
80
PHENOL → 2,4,6-TRIBROMOPHENOL OBSERVATION
COLOUR CHANGE
ORANGE TO COLOURLESS
WHITE PPT FORMS
81
PHENOL + 3x HBr
2,4,6-TRIBROMOPHENOL
82
HALOALKANE → NITRILE
CN- + EHTANOL
83
HALOALKANE + CN- + ETHANOL
NITRILE
84
CARBOXYLIC ACID → ACYL CHLORIDE
REAGENT; SOCl2 (thionyl chloride)
CONDITION: DRY (to stop other reaction)
forms acyl chloride + SO2 + HCl
85
CARBOXYLIC ACID → ACYL CHLORIDE TYPE OF REACTION
CHLORINATION
86
WHY DOES THE CARBOXYLIC ACID → ACYL CHLORIDE NEED TO BE DRY
TO STOP OTHER REACTIONS TAKING PLACE
87
CARBOXYLIC ACID + SOCl2
ACYL CHLORIDE
88
NITRILE →CARBOXYLIC ACID
REFLUX W/ DILUTE HCl
→ H2O, HCL, HEAT
EQUATION:
R-CH2-CN + 2H2O + HCl → R-CH2-COOH + NH4Cl
89
NITRILE →CARBOXYLIC ACID TYPE OF REACTION
HYDROLYSIS
90
NITRILE REFLUX W/ DILUTE HCl
CARBOXYLIC ACID
91
HALOALKANE → ALCOHOL
WARM NaOH (aq)
92
HALOALKANE + WARM NaOH (aq)
ALCOHOL
93
HALOALKANE → 1º AMINE
NUCLEOPHILIC SUBSTITUTION
REAGENT: EHTANOLIC AMMONIA
EQAUTION:
2 NH3 + CH3CH2Br →CH3CH3NH2 + NH4Br
94
HALOALKANE → AMINE TYPE OF REACTION
NUCLEOPHILIC SUBSTITUTION
95
ACYL CHLORIDE → 2º AMINE (+ HCl)
REAGENT: 1º AMINE
Cl comes off acyl chloride
H comes of NH2 of the 1º amine
these form HCl
96
ACYL CHLORIDE + 1º AMINE
2º AMINE + HCl
97
HALOALKANE + ETHANOLIC AMMONIA
1º AMINE
98
ALKANE → HALOALKANE
HALOGEN + UV
99
ALKANE → HALOALKANE FREE RADICAL SUBSTITUTION STEPS
e.g, using Cl2 + CH4
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
HOW DOES UV SPLIT THE HALOGEN IN FREE RADICAL SUBSTITUTION
HOMOLYTIC FISSION
