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Chemistry > 10 Amines > Flashcards

10 Amines Flashcards

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1
Q

Define ‘amine.’

A

organic derivative of ammonia in which one or more hydrogen atom is replaced with alkyl or aromatic groups

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2
Q

What makes amines both basic and nucleophilic?

A

the nitrogen atom with a lone pair of electrons on the ammonia group

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3
Q

What do amines occur in?

A

both plants and animals

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4
Q

State 3 examples of amines and identify them as primary or secondary.

A

NH₃ (primary)
CH₃NH₂ (secondary)
CH₃NHH₃C (secondary)

(see document for full structures)

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5
Q

Draw and name two examples of neurotransmitters which are amines and state their role.

(i.e. found in the brain)

A

dopamine (double-ringed) and serotonin
an essential role in brain chemistry
(see document for structures)

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6
Q

Draw and name an example of a hormone which is an amine and state its role.

(Hint = can we go back to…)
(Hint for structure = 3x the normal needed for response)

A

adrenaline (now called epinephrine)
triggers fight-or-flight response to stress
(see document for structures )

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7
Q

Draw and name four examples of alkaloids which are amines and state their roles and state the R-groups differ between two of them.

(Hint = 2 heavy pain-relief drugs and 2 available OTC & in shops)

(Hint = one found in drink with 2Os)

A 
morphine and codeine
For morphine R = H and for codeine R = CH₃
plant products used as synthetic drugs 
nicotine and caffeine 
act as stimulants 
(see document for structures)
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8
Q

Describe the bonding in a nitrogen atom and state what it is similar to using a diagram.

(Hint: 3 bonds)

A

3 single bonds and 1 lone pair
bonding in N is similar to that in ammonia
(see document for diagram)

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9
Q

Describe the bonding in aliphatic amines.

A

N is sp3 hybridised

C-N σ-bond is formed by the overlap of nitrogen sp3 and carbon sp3 orbitals

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10
Q

What is the C=N=C bond angle? (Hint: tetrahedral angle with further repulsion)

A

~ 107°

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11
Q

Describe the bonding in aromatic amines using a diagram.

Hint: benzene and 2 p-orbitals and 2 bonds

A

N is sp2 hybridised
lone pair occupies the p-orbital and is delocalised
(see document for diagram)

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12
Q

State, through definitions, how an amine is classified as:

a) primary (1°)
b) secondary (2°)
c) tertiary (3°)

A

a) one alkyl/aryl group is bonded to the nitrogen atom
b) two alkyl/aryl groups as substituents
c) three alkyl/aryl groups as substituents

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13
Q

Draw and classify as 1°, 2° or 3°:

a) trimethylamine
b) methylamine
c) dimethylamine

A

a) 3°
b) 1°
c) 2°
(see document for diagrams)

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14
Q

State the general IUPAC process of naming amines.

A

amines are named as alkanamines

the -e in alkane name of the largest chain is changed to amine

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15
Q

State the IUPAC process of naming secondary amines.

A

the longest carbon chain names the amine

the other alkyl groups are listed in alphabetical order as prefixes as N-alkyl groups

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16
Q

What are the common names of amines and how often are they used?

A

non-standard names are used more frequently than IUPAC

e.g. alkylamine, not alkaneamine; aniline not phenylalanine

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17
Q

For longer alkyl chains or more complex molecules, which prefix is used and what for?

A

the prefix amino-

to indicate the functional group

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18
Q

For the following primary amines state the IUPAC name, the common name and draw the structures:

a) CH₃CH₂CH₂NH₂CH₃
b) CH₃CH₂CH₂CH₂CH(NH₂)CH₃

A 
a) (3C alkane = propanone)
IUPAC name = propanamine
Common name = N-propylamine
b) 
IUPAC name  = hexan-2-amine
Common name = 2-amino hexane 
(see document for drawings)
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19
Q

Name the amine shown on the document in stages.

A

1 - find the longest chain and identify the corresponding alkane. Generate the amine name = propanamine
2 - identify the smaller alkyl groups attached to the nitrogen = methyl, ethyl
prefix the amine name with the names of the smaller alkyl groups listed in alphabetical order, each prefixed with N

You get N-ethyl-N-methyl-propanamine

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20
Q

In terms of physical properties, how soluble are amines and why?

A

low molecular weight, amines are generally soluble

also soluble in organic solvents

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21
Q

In terms of physical properties, what are the general boiling points of amines and why?

A

boiling points are relatively high

they are higher than alkanes but primary and secondary amines have lower boiling points than alcohols of similar mass

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22
Q

In terms of physical properties, what are the characteristic odours of some amines and why?

A

some low molecular weight amines have sharp, penetrating smells similar to ammonia
higher molecular weight amines are often found in decaying animal tissues

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23
Q

Which amines are responsible for the smell of rotting fish?

A

low molecular-weight amines

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24
Q

Where are higher molecular weight (Mr) amines often found?

A

in decaying animal tissues

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25
Q

Explain how hydrogen-bonding occurs in amines.

A

lone pair of electrons on N are hydrogen-bond acceptors

N-H bond in primary and secondary amines = H-bond donors

26
Q

How many hydrogen bonds can:

a) a primary amine form
b) a secondary amine form
c) a tertiary amine form

A

a) up to 3 H bonds
b) up to 2 H bonds
c) usually form 0 H bonds

27
Q

What is the only molecule that is the exception to tertiary amines forming 0 H-bonds and why?

A

water

only water is small enough to avoid steric hindrance here

28
Q

Draw hydrogen bonds between primary, secondary amines and water molecules (including lone pairs).

A

see document

29
Q

In terms of the chemical properties of amines, what are amines a type of and how?

A

weak organic bases

accept H⁺

30
Q

Because of the chemical properties of amines what do they produce when reacted with acids or water?

A

alkylammonium salts

31
Q

Finish the following general reaction between an tertiary amine and water on the document drawing out structures with correct bond types (on document).

A

see document for answer

32
Q

How are salts of amines named?

A

salts of amines are named by changing “amine” to “ammonium”

33
Q

Name the salt formed when trimethylamine reacts with water.

A

trimethylammonium hydroxide

34
Q

In terms of chemical properties, what does the formation of salts change?

A

change solubility, stability and crystallisation

35
Q

How can the change in chemical properties during the formation of salts be used?

A

in pharmaceutical calculations

36
Q

What is adderall and what is it made up of?

ASSS

A 
CNS stimulant used in the treatment of attention deficit hyperactivity disorder and narcolepsy
25% Amphetamine aspartate monohydrate
25% Amphetamine sulfate
25% Dextroamphetamine sulfate
25% Dextroamphetamine saccharate
37
Q

Draw out the chemical structure of Adderall.

A

see document for this

38
Q

State how primary amines are chemically synthesised by ‘reduction of nitro compounds’ including:

a) reagents
b) conditions
c) the general reaction equation

(Hint: N”O₂”)

(Ar = alkyl)

A

a) Ar-NO₂
b) H₂, transition metal catalyst (i.e. Ni, Pt, Pd)
(Hint: N”O₂”= transiti”O”n metal catalyst)
c) Ar-NO₂ → ArNH₂

39
Q

State how primary amines are chemically synthesised by ‘reduction of nitriles’ including:

a) reagents
b) conditions
c) the general reaction equation

(Hint = “Ni”trile compound)

A

a) RC≡N
b) H₂, Ni catalyst
c) RC≡N → RC-NH₂

40
Q

State how primary, secondary and tertiary amines are chemically synthesised by ‘reduction of amides’ including:

a) reagents
b) conditions
c) the general reaction equation

(Hint = not counted as an O)

A

a) RC=ON(R’’)(R’)
b) LiAlH₄
c) (see document for this)

41
Q

State how primary amines are chemically synthesised by ‘Hoffman degradation of amides’ including:

a) reagents
b) conditions
c) the general reaction equation

A

a) RC=ONH₂
b) KOBr
c) RC=O-NH₂ → R-NH₂

42
Q

Provide the reaction for primary amines to be produced from alcohols in industry. State:

a) reagents
b) conditions
c) the general reaction equation (draw out too)

A

a) alcohol and ammonia
b) High temperature and high pressure
c) ROH + NH₃ → R-NH₂ + H₂O (see document for diagrams)

43
Q

In the lab, what can alkyl halides be used as and how often are they used synthetically?

A

an alkylating agent

not often used synthetically, as the reaction is difficult to control

44
Q

Draw out the general reaction equation for alkylamines production from an alkyl halide.

A

see document for this

45
Q

Describe the properties of the lone pair of electrons ammonia molecule and explain why they are present.

(Hint: charge on N atom)

A

electron-rich/basic:
electron-pair donor
H⁺ acceptor

nucleophilic (-):
react with centres of positive charge

46
Q

Provide the reaction for ‘condensation’ with carbonyls. State:

a) reagents
b) the general reaction equation (draw out too)
c) state the functional group created
d) state the type of base created

A

a) NH₃
b) R(R’)C=O → R(R’)=NH
(see document for diagram)
c) imine (=NH)
d) schiff base (with imine group)

47
Q

Provide the reaction for ‘reductive amination’ of carbonyls. State:

a) reagents
b) the 3 different types of conditions
c) the general reaction equation (draw out too)

(Hint: carb”O”nyls)

A 
a) NH₃, H₂
OR NaBH₃CN
OR NaBH(OAc)₃
b) transition metal catalyst 
c) R(R')C=O → R₂C-NH₂
48
Q

What is the chemical importance of reductive amination of aldehydes/ketones?

A

synthesis of primary, secondary and tertiary amines

49
Q

State the biological importance of condensation with carbonyls in nitrogen metabolism drawing out the multi-stage example including enzymes.

A

NH₄⁺ + α-ketoglutarate + amino acid (NADPH₂, glutamate dehydrogenase) → glutamate (NH₃, ATP, glutamine synthetase) → glutamine

(see document for structures)

50
Q

State the biological importance of condensation with carbonyls in the transfer of NH₂ groups drawing out the example including enzymes.

A

glutamate + keto-acid → α-keto glutarate + amino acid
(aminotransferase)
(see document for structures)

51
Q

State the biological importance of condensation with carbonyls in enzyme mechanisms drawing out the example including enzymes.

A

pyridoxal phosphate-dependent enznymes, photosynthesis
pyridoxal phosphate → enzyme
(see document for structures)

52
Q

State the products of the following general ‘acid-base’ reaction and state what the amine group acts as. (draw out on document too)

RR’R”N: + H-A ⇌

(Hint: split reagents 2 into positive and negative ions)

A

amine = base
RR’R”N: + H-A ⇌ RR’R”NH⁺A- + H-A
(see document for equation)

53
Q

State the products of the following general ‘alkylation’ reaction and state what the amine group acts as. (see document for reaction)

(Hint: split reagents 2 into positive and negative ions)

A

amine = nucleophile

see document for equation

54
Q

State the products of the following general ‘acylation’ reaction and state what the amine group acts as. (see document for reaction):

HO₂C-C(CH₃)-NH₂ + RC=OCl →

(Hint: split reagents 2 into positive and negative ions)

A

amine = nucleophile

see document for equation

55
Q

Give a biological example of an ‘acylation’ reaction and state the enzyme involved.

A

(see document for this)

56
Q

State the general reaction for diazonium salt formation.

A

(see document for this)

57
Q

What characteristic do aliphatic diazonium salts (R= alkyl) have and how do they compare with aromatic diazonium (R = Ar) salts; what does this mean?

A

aliphatic are very unstable
aromatic are more, stable
thus aromatic are more useful

58
Q

Finish the following diagram for aromatic amine formation (on document)

A

see document

59
Q

What is Hoffman elimination and what is it used for?

A

used to produce an alkene and a tertiary amine from a tertiary amine
used primarily as a method for the production of alkenes

60
Q

Draw out the Hoffman elimination reaction stages.

A

see document

Chemistry (12 decks)

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