3.14 Synthetic routes Flashcards
1
Q
What are the conditions when making a poly(alkene) from an alkene?
A
- High pressure
- Catalyst
2
Q
What are the conditions when making a dihalogenoalkane from an alkene?
A
Room temperature
3
Q
What are the conditions when making a diol from a dihalogenoalkane?
A
Heat under reflux
4
Q
What are the reagents when making a dihalogenoalkane from an alkene?
A
Br2
Cl2
5
Q
What are the reagents when making a diol from a dihalogenoalkane?
A
KOH aqueous
6
Q
What is the mechanism when making a dihalogenoalkane from an alkene?
A
Electrophilic addition
7
Q
What is the mechanism when making a diol from a dihalogenoalkane?
A
Nucleophilic substitution
8
Q
What are the reagents when making a halogenoalkane from an alkene?
A
HBr
HCl
9
Q
What are the conditions when making a halogenoalkane from an alkene?
A
Room temperature
10
Q
What is the mechanism when making a halogenoalkane from an alkene?
A
Electrophilic addition
11
Q
What are the reagents when making a halogenoalkane from an alkane?
A
Br2
Cl2
12
Q
What are the conditions when making a halogenoalkane from an alkane?
A
UV light
13
Q
What is the mechanism when making a halogenoalkane from an alkane?
A
Free radical substitution
14
Q
What are the reagents when making an alkene from a halogenoalkane?
A
KOH alcoholic
15
Q
What are the conditions when making an alkene from a halogenoalkane?
A
Heat under reflux
16
Q
What is the mechanism when making an alkene from a halogenoalkane?
A
Elimination
17
Q
What are the reagents when making an alcohol from a halogenoalkane?
A
KOH aqueous
18
Q
What are the conditions when making an alcohol from a halogenoalkane?
A
Heat under reflux
19
Q
What is the mechanism when making an alcohol from a halogenoalkane?
A
Nucleophilic substitution
20
Q
What are the reagents when making an alkene from an alcohol?
A
Conc. H2SO4
Con H3PO4
21
Q
What is the mechanism when making an alkene from an alcohol?
A
Elimination, dehydration
22
Q
What are the reagents when making an alcohol from an alkene?
A
Step 1 - H2SO4
Step 2 - H2O
23
Q
What is the mechanism when making an alcohol from an alkene?
A
Step 1 - Electrophilic addition
Step 2 - Hydrolysis
24
Q
What are the conditions when making an alcohol from an alkene?
A
Step 2 - warm
25
What are the reagents when making an alcohol from an aldehyde?
NaBH4
26
What is the mechanism when making an alcohol from an aldehyde?
Reduction, Nucleophilic substitution
27
What are the reagents when making an aldehyde from a primary alcohol?
Na2Cr2O7/H+
28
What are the conditions when making an aldehyde from a primary alcohol?
Heat and distill
29
What is the mechanism when making an aldehyde from a primary alcohol?
Partial oxidation
30
What are the reagents when making a ketone from a secondary alcohol?
NaCr2O7/H+
31
What are the condtions when making a ketone from a secondary alcohol?
Heat
32
What is the mechanism when making a ketone from a secondary alcohol?
Oxidation
33
What are the reagents when making an alcohol from a ketone?
NaBH4
34
What is the mechanism when making an alcohol from a ketone?
Reduction, Nucleophilic addition
35
What are the reagents when making a hydroxynitrile from an aldehyde?
NaCN + H2SO4
36
What is the mechanism when making a hydroxynitrile from an aldehyde?
Nucleophilic addition
37
What are the reagents when making a hydroxynitrile from a ketone?
NaCN + H2SO4
38
What is the mechanism when making a hydroxynitrile from a ketone?
Nucleophilic addition
39
What are the reagents when making a carboxylic acid from an aldehyde?
(if primary) Na2Cr2O7/H+
40
What are the conditions when making a carboxylic acid from an aldehyde?
Heat under reflux + excess oxidising agent
41
What is the mechanism when making a carboxylic acid from an aldehyde?
Oxidation
42
What are the reagents when making an ester from a carboxylic acid?
Alcohol +. H2SO4
43
What are the conditions when making an ester from a carboxylic acid?
Heat
44
What is the mechanism when making an ester from a carboxylic acid?
Esterification
45
What are the reagents when making a carboxylic acid from an acyl chloride / acid anhydride?
H2O
46
What are the conditions when making a carboxylic acid from an acyl chloride / acid anhydride?
Room temperature
47
What is the mechanism when making a carboxylic acid from an acyl chloride / acid anhydride?
Nucleophilic addition / elimination
48
What are the reagents when making an ester from an acyl chloride / acid anhydride?
Alcohol
49
What are the conditions when making an ester from an acyl chloride / acid anhydride?
Room temperature
50
What is the mechanism when making an ester from an acyl chloride / acid anhydride?
Nucleophilic addition / elimination
51
What are the reagents when making a primary amide from an acyl chloride / acid anhydride?
NH3
52
What are the conditions when making a primary amide from an acyl chloride / acid anhydride?
Room temperature
53
What is the mechanism when making a primary amide from an acyl chloride / acid anhydride?
Nucleophilic addition/elimination
54
What are the reagents when making a secondary amide from an acyl chloride / acid anhydride?
1º amine
55
What are the conditions when making a secondary amide from an acyl chloride / acid anhydride?
Room temperature
56
What is the mechanism when making a secondary amide from an acyl chloride / acid anhydride?
Nucleophilic addition/elimination
57
What are the reagents when making an ester from an alcohol?
Carboxylic acid + H2SO4
58
What are the conditions when making an ester from an alcohol?
Heat
59
What is the mechanism when making an ester from an alcohol?
Esterification
60
What are the reagents when making a secondary amide from a 1º amine?
Acyl chloride
61
What are the conditions when making a secondary amide from a 1º amine?
Room temperature
62
What is the mechanism when making a secondary amide from a 1º amine?
Nucleophilic addition/elimination
63
What are the reagents when making a 2º amine, 3º amine, quaternary amine from a 1º amine?
Halogenoalkane
64
What is the mechanism when making a 2º amine, 3º amine, quaternary amine from a 1º amine?
Nucleophilic substitution
65
What are the reagents when making a 1º amine from a nitrile?
LiAlH4
66
What is the mechanism when making a 1º amine from a nitrile?
Reduction
67
What are the reagents when making a 1º amine from a halogenoalkane?
Alcoholic NH3
68
What are the conditions when making a 1º amine from a halogenoalkane?
Heat under pressure
69
What is the mechanism when making a 1º amine from a halogenoalkane?
Nucleophilic substitution
70
What are the reagents when making a nitrile from a halogenoalkane?
KCN in ethanol/ water mixture
71
What are the conditions when making a nitrile from a halogenoalkane?
Heat under reflux
72
What is the mechanism when making a nitrile from a halogenoalkane?
Nucleophilic substitution
73
What are the reagents when making benzene-NO2 from benzene?
Conc nitric acid + conc sulphuric acid
74
What is the mechanism when making benzene-NO2 from benzene?
Electrophilic substitution
75
What are the reagents when making benzene-NH2 from benzene-NO2?
Sn and HCl
76
What is the mechanism when making benzene-NH2 from benzene-NO2?
Reduction
77
What are the reagents when making benzene-NH-CH3 from benzenes-NH2
CH3Cl
78
What is the mechanism when making benzene-NH-CH3 from benzenes-NH2
Nucleophilic substitution
79
What are the reagents when making benzene-NH-CO-CH3 from benzenes-NH2?
CH3COCl
80
What is the mechanism when making benzene-NH-CO-CH3 from benzenes-NH2?
Nucleophilic addition-elimination
81
What are the reagents when making benzene-CO-CH3 from benzene?
Acyl chloride in the presence of an anhydrous aliminium chloride catalyst.
82
What is the mechanism when making benzene-CO-CH3 from benzene?
Electrophilic substitution
83
What are the reagents when making benzene-C(OH)(CN)CH3 from benzene-CO-CH3?
NaCN + H2SO4
84
What is the mechanism when making benzene-C(OH)(CN)CH3 from benzene-CO-CH3?
Nucleophilic addition
85
What are the reagents when making benzene-C(OH)(CH3)(CH2-NH2) from benzene-C(OH)(CN)CH3?
LiAlH4
86
What is the mechanism when making benzene-C(OH)(CH3)(CH2-NH2) from benzene-C(OH)(CN)CH3?
Reduction
87
What are the reagents when making benzene-CH(OH)Ch3 from benzene-CO-CH3?
NaBH4
88
What is the mechanism when making benzene-CH(OH)CH3 from benzene-CO-CH3?
Reduction, Nucleophilic addition
89
What are the reagents when making benzene-CH(CH3)(O-CO-CH3) from benzene-CH(OH)CH3?
CH3CO2H + H2SO4
90
What are the conditions when making benzene-CH(CH3)(O-CO-CH3) from benzene-CH(OH)CH3?
Heat
91
What is the mechanism when making benzene-CH(CH3)(O-CO-CH3) from benzene-CH(OH)CH3?
Esterification
92
Why are the use of solvents generally avoided?
(see page 2 in the chemrevise revision guide)
93
What is distillation used for?
In general used as a separation technique to separate an organic product from its reacting mixture. Need to collect the distillate of the approximate boiling point range of the desired liquid.
94
Using distillation for the reaction of a primary alcohol -> aldehyde:
What are the reagents?
What are the conditions?
What are the observations?
(see page 3 in the chemrevise revision guide)
95
Draw and label a diagram of distillation apparatus.
(see page 3 in the chemrevise revision guide)
96
What is reflux used for?
Reflux is used when eating organic reaction mixture for long periods. The condenser prevents organic vapours from escaping by condensing them back to liquids.
97
Why should you never seal the end of the condenser in a reflux apparatus?
As the build up of gas pressure could cause the apparatus to explode. This is true of any apparatus were volatile liquids are heated.
98
Using reflux for the reaction of a primary alcohol -> carboxylic acid:
What are the reagents?
What are the conditions?
What are the observations?
(see page 3 in the chemrevise revision guide)
99
Draw and label a diagram of reflux apparatus.
(see page 3 in the chemrevise revision guide)
100
Why are anti-bumping granules added to both distillation and reflux apparatus?
To prevent vigorous, uneven boiling by making small bubbles form instead or large bubbles.
101
Why are electric heaters often used to heat organic chemicals?
Organic chemicals are normally highly flammable and could set on fire with a naked flame.
102
Describe the method for fractional distillation in the lab.
(see page 4 in the chemrevise revision guide)
103
Draw and label the apparatus for fractional distillation in the lab.
(see page 4 in the chemrevise revision guide)
104
How can we measure boiling point?
Distillation, used to determine the purity of a liquid.
| see page 4 in the chemrevise revision guide
105
What is fractional distillation used for?
Fractional distillation is used to separate liquids with different boiling points.
106
Identify the general method for how you would purify an organic liquid using a separating funnel.
(see page 5 in the chemrevise revision guide)
