1.Chemistry > 3.3.11 Amines Knowledge > Flashcards

3.3.11 Amines Knowledge Flashcards

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1
Q

what is a base

A

proton acceptor

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2
Q

what are amines

A

derivatives of ammonia with one or more of the H atoms replaced by an alkyl or aryl group

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3
Q

what are primary amines

A

one R group attached to ammonia: RNH2

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4
Q

what are secondary amines

A

2 R groups attached to ammonia: RRNH

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5
Q

how do you name a primary amine

A

The name of the amine comes from the name of the R group

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6
Q

what are tertiary amines

A

3 R groups attached to ammonia: RRRN

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7
Q

name this molecule

A

ethylamine or aminoethane

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8
Q

draw ethylamine

A
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9
Q

draw phenylamine

A
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10
Q

draw diethylamine

A
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11
Q

how do you name secondary amines with two different R groups

A

R groups should be listed in size order, smallest to largest. N is used to show that the R group is attached to the N atom.

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12
Q

name this molecule

A

N-methyl-N-propylamine

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13
Q

draw N-methyl-N-propylamine

A
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14
Q

name this molecule

A

N-methyl-N-butylamine

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15
Q

draw N-methyl-N-butylamine

A
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16
Q

draw (N,N,N) triphenylamine

A
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17
Q

name this molecule

A

(N,N,N) triphenylamine

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18
Q

draw N,N-dimethyl N-ethylamine

A
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19
Q

name this molecule

A

N,N-dimethyl N-ethylamine

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20
Q

name this molecule

A

methyl N-ethyl-N-butylamine

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21
Q

draw methyl N-ethyl-N-butylamine

A
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22
Q

draw 2-aminobutane

A
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23
Q

NAME this molecule

A

2-aminobutane

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24
Q

what charge do quaternary ammonium salts have and why

A

4 R groups attached to the N atom, which makes it positive
There will be a negative ion paired up with the quaternary ammonium ion

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25
draw (N,N,N,N)-tetramethylammonium chloride
26
name this molecule
(N,N,N,N)-tetramethylammonium chloride
27
why can amines act as bases
there is a lone electron pair on the nitrogen which can accept a proton to form an ammonium ion
28
write an equation showing ethylamine can act as a base
C₂H₅NH₂ + H⁺ ⇒ C₂H₅NH₃⁺
29
write an equation showing dimethylamine can act as a base
(CH₃)₂NH + H⁺ ⇒ (CH₃)₂NH₂⁺
30
what is the strength of an amine base determined by
how available the nitrogen lone pair is to accept a proton
31
put these molecules in order from strongest to weakest base: - phenyl amine - diphenyl amine - triphenyl amine - primary amine - secondary amine - tertiary amine - ammonia
Strongest: tertiary amine - secondary amine - primary amine - ammonia - phenyl amine - diphenyl amine Weakest: triphenyl amine
32
compare the ability of a tertiary amine and ammonia to act as a base
- Positive inductive effect of alkyl groups releases electron density towards N atom - Lone pair of electrons on N is more available - Stronger base than ammonia
33
compare the ability of phenylamine and ammonia to act as a base
- Lone pair of electrons on N atom delocalises into benzene ring - Lone pair of electrons on N is less available - Weaker base than ammonia
34
what happens when an amine acts as a base
it accept a proton to form an ammonium ion
35
write an equation for the reaction between ammonia and hydrochloric acid
NH₃ + HCl ⇒ NH₄Cl
36
write an equation for the reaction between ethylamine and nitric acid
C₂H₅NH₂ + HNO₃ ⇒ C₂H₅NH₃NO₃
37
name NH₄Cl
ammonium chloride
38
name C₂H₅NH₃NO₃
ethyl ammonium nitrate
39
how can primary amines be formed via nucleophilic substitution
Primary amines can be formed via a nucleophilic substitution reaction between a haloalkane and ammonia
40
describe how tetramethylammonium chloride can be formed from chloromethane
-The product of the reaction between chloromethane and ammonia is methylamine, a primary amine - As methylamine also has a lone pair on the nitrogen, it can carry out the same mechanism again to form a secondary amine - The product of the reaction between methylamine and chloromethane is dimethylamine, a secondary amine - As dimethylamine also has a lone pair on the nitrogen, it can carry out the same mechanism again to form a tertiary amine - The product of the reaction between dimethylamine and chloromethane is trimethylamine, a tertiary amine - As trimethylamine also has a lone pair on the nitrogen, it can carry out the same mechanism one more time - The product of the reaction between trimethylamine and chloromethane is tetramethylammonium chloride, a quaternary ammonium salt
41
draw a mechanism for the reaction between bromoethane and ammonia under reflux
42
draw a mechanism for the reaction between methylamine and bromomethane
43
draw a mechanism for the reaction between bromomethane and dimethylamine
44
draw the mechanism for the reaction between bromomethane and trimethylamine
45
why will there be mixture of products when reacting a haloalkane with ammonia
When reacting a haloalkane, you cannot completely control how much primary, secondary, and tertiary amines, and quaternary ammonium salt, will form. There will be a mixture of all these products
46
why is using nucleophilic substitution not an efficient method of forming a specific amine
When reacting a haloalkane, you cannot completely control how much primary, secondary, and tertiary amines, and quaternary ammonium salt, will form. There will be a mixture of all these products
47
how do you get a higher yield of the primary amine in the nucleophilic substitution of haloalkanes and ammonia
To ensure a higher yield of the primary amine, use excess ammonia, as further substitution requires excess haloalkane
48
how do the products of a further substitution reaction of haloalkanes and ammonia change each time
To find the products of a further substitution reaction, an alkyl group is added to the N each time
49
what are amines used for
Amines can be used to form amides, which in turn can be used to make: polymers like nylon, dyes, drugs and pharmaceuticals
50
what are quaternary ammonium salts used for
Quaternary ammonium salts are used in hair conditioner and fabric softener - cationic surfactants
51
what method is best to produce a primary amine and why
If a primary amine is the desired product, reduce a nitrile as there is no risk of secondary, tertiary, or quaternary products forming
52
explain how haloalkanes become amines via nucleophilic substitution then reduction
- Haloalkanes can undergo a nucleophilic substitution with a cyanide ion, from KCN, in ethanolic and aqueous conditions - The nitrile formed can then be reduced to an amine functional group
53
draw the mechanism for the reaction between KCN and chloromethane
54
draw a displayed equation for the reduction of ethanenitrile
55
what is the reagent for the reduction of nitriles
hydrogen
56
what is the condition for the reduction of nitriles
nickel catalyst
57
compare 2 routes to synthesise amines
58
what are the reagents and conditions required to synthesise phenylamine
conc. HCl and tin catalyst
59
describe the synthesis of phenylamine
- Nitrobenzene is made via an electrophilic substitution reaction using benzene, HNO₃, and H₂SO₄: C6H6 + HNO3 ⇒ C6H5NO2 + H2O - The nitro group can then be reduced to an amine functional group: C6H5NO2 + 6[H] ⇒ C6H5NH2 + 2H2O - Overall equation: C6H6 ‒conc. H₂SO₄, 25-60 degrees⇒ C6H5NO2 ‒Sn, conc. HCl, NaOH(aq)⇒ C6H5NH2 + 2H2O - As this process takes place in the presence of HCl, the product formed can react to form phenyl ammonium chloride (phenylamine is a base, and HCl is an acid): - To prevent phenyl ammonium chloride forming, NaOH can be added which is a stronger base:
60
draw the mechanism for the formation of nitrobenzene
61
write an equation for the reaction between phenyl ammonium chloride and NaOH
C6H5NH3+ Cl- + NaOH ⇒ C6H5NH2 + NaCl + H2O
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