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chemistry > topic 18B > Flashcards

topic 18B Flashcards

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1
Q

amine functional group

A

-yl
- e.g. propylamine

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2
Q

amide functional froup

A

-amide
- e.g. ethanamide

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3
Q

identifying an amino acid

A
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4
Q

aliphatic amines

A
  • non-aromatic amines are aliphatic amines
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5
Q

how is an aliphatic amine formed

A
  • either by reacting a halogenoalkane with excess ammonia
  • or by reducing a nitrile
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6
Q

why do primary aliphatic amines act as Bronsted-Lowry bases?

A
  • the lone pair of electrons on the nitrogen is readily available to form a dative covalent bond with a H+
  • it is accepting a proton
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7
Q

why are primary aliphatic amines stronger bases than ammonia?

A
  • primary aliphatic amines are stronger bases than ammonia
  • the alkyl groups are electron releasing and push electrons towards the nitrogen atom
  • making it a stronger base
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8
Q

what’s the stronger base - primary or secondary amine and why?

A
  • secondary are stronger
  • they have more alkyl groups
  • more electron density is pushed onto the N atom
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9
Q

what’s the stronger base - secondary or tertiary amine

A
  • secondary
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10
Q

reaction of primary aliphatic amines with water

A
  • small amines can form hydrogen bonds with water
  • forming an alkaline solution
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11
Q

reaction of primary aliphatic amines with water example

A

CH3CH2NH2 + water –> CH2CH2NH3+ + OH-

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12
Q

reaction of primary aliphatic amines with acids

A
  • react with acids to form salts
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13
Q

reaction of primary aliphatic amines with acids - example

A

CH3NH2 + HCl -> CH3NH3+Cl-

methylamine + HCl -> mehtylammonium chloride

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14
Q

reaction of primary aliphatic amines with ethanoyl chloride - type of reaction?

A

addition-elimination reaction
- two molecules join together and a small molecule is eliminated

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15
Q

reaction of primary aliphatic amines with ethanoyl chloride - example

A

CH3CH2NH2 + CH3COCl -> CH3CONH

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16
Q

what does the reaction with ethanoyl chloride lead to

A
  • it leads to the formation of a new functional group
  • carbonyl group is next to the NH group
17
Q

reaction of primary aliphatic amines with halogenoalkanes - type of reaction

A
  • halogenoalkanes undergo nucelophilic substitution
  • form secondary amines
18
Q

reaction of primary aliphatic amines with halogenoalkanes - example

A

butylamine + chloroethane -> N-ethylbutylamine + HCl

19
Q

reaction of primary aliphatic amines with copper (II) ions - what is formed

A

complex ions

20
Q

how are these complex ions formed

A
  • lone pair of electrons on the nitrogen allows amines to act as ligands
  • hence they form dative covalent bonds inot transition metal ions to form coloured complex ions
21
Q

reaction of primary aliphatic amines with copper (II) ions - example

A

4 CH3CH2NH2 + Cu(H2O)6 2+ ⇌ [Cu(CH3CH2NH2)4(H2O2)2]2+ + 4 H2O

22
Q

reaction of primary aliphatic amines with copper (II) ions - example (ammonia as the ligand)

A

4NH3 + Cu(H2O)6 2+ ⇌ [Cu(NH3)4(H2O)2]2+ + 4H2O

light blue solution ⇌ deep blue solution

23
Q

do primary aromatic amines for basic solutions?

A
  • no
  • the lone pair of electrons on the nitrogen delocalise with the ring of electrons on the benzene ring
  • N is less acceptable to protons
24
Q

difference in basicity of ammonia, primary aliphatic amines and primary aromatic amines

A
  • ammonia is more basic than aromatic amines - there is no partial delocalisation of N lone pair
  • aliphatic amines are more basic than both ammonia and aromatic amines - alkyl groups have an inductive effect on the N lone pair
25
Q

what is meant by inductive effect

A

The effect on electron density in one portion of a molecule

26
Q

formation of primary aliphatic amines from halogenoalkanes
- reagents
- conditions
- type of reaction

A
  • excess ammonia
  • ethanol and heat
  • nucleophilic substitution
27
Q

formation of primary aliphatic amines from halogenoalkanes details

A
  • the nitrogen lone pair on the ammonia acts as a nucleophile and replaces the halogen on the halogenoalkane
  • when halogenoalkane is reacted with excess ammonia, hot ethanol under pressure, a primary amine is formed
28
Q

formation of primary aliphatic amines from the reduction of nitriles
- reagents
- conditions
- type of reaction

A
  • aqueous ethanol, LiAlH4 in dry ether, nickel catlayst
  • heat under reflux
  • reduction
29
Q

formation of primary aliphatic amines from the reduction of nitriles details

A
  • nitriles contain a -CN group which can be reduced to an -NH2 group
  • nitrile vapour and H2 gas are passed over a nickel catlayst or LiAlH4 in dry ether and can be used to form a primary amine
30
Q

how can aromatic nitroarenes be reduced to form amines?
- reagents
- conditions
- mechanism

A
  • tin and HCl
  • iron and HCl
  • heating
  • reduction
31
Q

preparing amides
- change in functional group
- reagent
- condition

A
  • acyl chloride to secondary amide
  • primary amine
  • room temperature

chemistry (28 decks)

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