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17.5 Flashcards

1
Q

what are amines

A

nitrogen containing compounds

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2
Q

explain the structure of an amine

A

3 bonding pairs with at least one alkyl group
1 lone pair
trigonal pyramidal shape

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3
Q

what is a primary amine

A

nitrogen is attached to 1 alkyl group

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4
Q

what is a secondary amine

A

nitrogen is attached to 2 alkyl groups

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5
Q

what is a tertiary amine

A

nitrogen is attached to 3 alkyl groups

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6
Q

whats the name of the compound C6H5NH2

A

phenylamine

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7
Q

what is the equation for the preparation of a primary amine from a halogenoalkane

A

CH3Cl + NH3 -> CH3NH2 + HCl

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8
Q

what is the equation for the preparation of a secondary amine from a halogenoalkane

A

CH3Cl + CH3NH2 -> (CH3)2NH + HCl

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9
Q

what are the 2 ways of forming amines from halogenoalkanes

A

heating with ammonia under pressure in a sealed container
or mix with aqueous ammonia

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10
Q

how does the formation of amines from halogenoalkanes involve and nucleophilic attack

A

lone pair on ammonia act as nucleophile and attack the electron deficient carbon, the amine formed then acts as a nucleophile and attacks another electron deficient carbon to form a secondary amine

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11
Q

how can the number of secondary amines being formed from the products of halogenoalkanes and ammonia be reduced

A

ammonia is used to excess so that it outnumbers the molecules of primary amines formed and some of the excess ammonia reacts with the HCl to form NH4Cl

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12
Q

what is the equation for the reduction of ethanenitrile

A

CH3CN + 4[H] -> CH3CH2NH2

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13
Q

what are the conditions and the reagent for the reduction of nitriles to primary amines

A

reducing agent - lithiumtetrahydridoaluminate
mixed in dry ether

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14
Q

why must the reduction of nitriles to primary amines be in dry ether

A

so that no water can affect the reaction

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15
Q

whats the equation for the reduction of nitrobenzene

A

C6H5NO2 + 6[H] -> C6H5NH2 + 2H2O

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16
Q

what are the reagents and conditions for reduction of nitrobenzene to phenylamine

A

reducing agent (tin) and concentrated hydrochloric acid
heated under reflux

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17
Q

how does phenylamine react with acids

A

forms phenyl ammonium ion (C6H5NH3+)

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18
Q

how can phenyl ammonium ion be converted back to phenylamine

A

added alkali (sodium hydroxide)
C6H5NH3+ + OH- -> C6H5NH2 + H2O

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19
Q

what are phenylamines commonly used for

A

dying blue jeans
manufacturing polymers
pharmaceuticals

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20
Q

what is the trend in solubility of primary aliphatic amines as hydrocarbon chain decreases

A

as hydrocarbon chain increases solubility decreases

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21
Q

why are amines soluble in water

A

their lone pair on the nitrogen allows them to form hydrogen bonds with the water molecules

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22
Q

how can amines act as a base when mixed with water

A

the nitrogen uses its lone pair to form a dative bond with the hydrogen on the water molecule
CH3NH2 + H2O <=> CH3NH3+ + OH-

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23
Q

how does ammonia act as a base when mixed with water

A

the nitrogen uses its lone pair to form a dative bond with the hydrogen on the water molecule
NH3 + H2O <=> NH4+ + OH-

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24
Q

what is basicity

A

the extent to which a base can donate a lone pair of electrons to the hydrogen atom of a water molecule

25
what is the trend is basicity of amines as the hydrocarbon chain length increases and why
basicity strength increases as chain length increases because the alkyl groups are electron-releasing so increase the density of the nitrogen and make it more open to donate its lone pair
26
is ammonia a stronger or weaker base than alkylamines
weaker
27
is phenyl amine a strong or weak base and why
weak base because the lone pair on the nitrogen are attracted to the delocalized pi bond making the nitrogen less electron rich and making the lone pair less available for donating
28
how do amines react with acids
they all react with strong acids to form ionic salts
29
what is the equation for the reaction between methylamine and nitric acid
CH3NH2 + HNO3 -> CH3NH3+ + NO3-
30
what is the equation for the reaction between butylamine and hydrochloric acid
CH3CH2CH2CH2NH2 + HCl -> CH2CH2CH2CH2NH3+ + Cl-
31
what is an addition-elimination reaction
occurs when 2 molecules join together, followed by the loss of a small molecule
32
what is an amide
carbonyl group next to a NH group
33
why do amines react with halogenoalkanes and what is produced
the electron deficient carbon reacts with the electron rich nitrogen to form a secondary amine a hydrogen halide
34
what is the equation for the reaction between butylamine and chloroethane
CH3CH2CH2CH2NH2 + CH3CH2Cl -> CH3CH2CH2CH2NHCH2CH3 + HCl
35
what happens if the products of the reaction between a halogenoalkane and alkylamine react further
the secondary amine will react with the halogenoalkane and form a tertiary amine and a halogen ion
36
what is a quaternary ammonium salt
an ammonium ion in which all of the hydrogens have been replaced by alkyl groups
37
why is reacting amines with halogenoalkanes not a good way of preparing primary/secondary/ tertiary amines
because the product gives a mixture of similar products
38
give a use on quaternary ammonium salts
fabric softener
39
what is the equation for the reaction of ammonia with hexaaquacopper(II)
[Cu(H2O)6]2+ + 4NH3 -> [Cu(NH3)4(H2O)2]2+ + 4H2O
40
what will be observed when an amine reacts with hexaaquacopper(II)
first a blue precipitate will form then as the amine is added in excess it will dissolve and a deep blue solution will form
41
what is the functional group of an amide
carbonyl group joined to an amino group CONH2
42
what are the properties of amides
solids lower aliphatic amides are soluble low mp & bp
43
why are lower aliphatic amides soluble
because the central carbon atom is attached to an oxygen and a nitrogen which are very electronegative so the bonds are polar and have lone pairs which help to form hydrogen bonds with water
44
what two molecules form a polyamide
a dicarboxylic acid and a diamine
45
draw the structure of an amino acid
46
what is the isoelectric point
the pH of an aqueous solution in which it is neutral
47
what is a zwitterion
a molecule containing positive and negative charges but which have no overall charge
48
are amino acids soluble
yes
49
what is the equation for an amino acid acting as a base
H2NCHRCOOH + H2O <=> H3N+CHRCOOH + OH-
50
what is the equation for an amino acid acting as an acid
H2NCHRCOOH + H2O <=> H2NCHRCOO- + H3O+
51
what does the isoelectric point tell you about the acidity or alkalinity of a zwitterion
low isoelectric point = predominantly acidic high isoelectric point = predominantly basic
52
are amino acids optically active
yes except glycine
53
what is a peptide bond
the bond formed by a condensation reaction between the carbonyl group of one amino acid and the amino group of another amino acid
54
what type of reaction occurs when two amino acids react together
acid-base reaction
55
what is the difference between a long-chain polypeptide and a protein
proteins have more complex 3D structures, primary. secondary, tertiary, quaternary
56
how can a protein be broken down into their individual amino acids
heat with concentrated HCl to break peptide bond
57
how can chromatography be carried out on proteins to identify amino acids
hydrolyse a protein so a mixture of amino acids is produced, spot the protein on chromatography paper and using a suitable solvent the individual amino acids will rise to different heights however amino acids are colourless so the chromatogram must be prayed with a developing agent (ninhydrin) so that the position of the amino acids can be seen
58
what developing agent is used for the chromatography of amino acids
ninhydrin
59
why is ninhydrin not used often
it is toxin

Chemistry (46 decks)

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