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Chemistry > 27 - Amines, amino acids and polymers > Flashcards

27 - Amines, amino acids and polymers Flashcards

1
Q

aliphatic amine?

A

nitrogen attached to at least one straight or branched carbon chain

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2
Q

aromatic

A

nitrogen atom is attached to an aromatic ring

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3
Q

how to name amine with a NH2 group on carbon 1

A

alkyl chain - amine

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4
Q

how to name an amine with NH2 not on carbon 1

A

use prefix amino

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5
Q

how to name secondary or tertiary amines containing the same alkyl group on the nitrogen

A

di of tri indicates number of alkyl groups

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6
Q

how to name secondary or tertiary amines with different alkyl groups attached to the nitrogen atom
CH3NHCH2CH2CH3
CH3N(CH2CH3)CH2CH2CH3

A

N-substituted derivative
CH3NHCH2CH2CH3 N-methylpropylamine
CH3N(CH2CH3)CH2CH2CH3 N-ethyl-Nmethylpropylamine

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7
Q

Explain how amines act as bases?

A
  • they have a lone pair on their nitrogen atom and it can accept a proton
  • this forms a dative covalent bond between nitrogen and hydrogen
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8
Q

Amine + Salt
CH3CH2CH2NH2 + HCl

A

-> acids
CH3CH2CH2NH+CL-
neutralisation

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9
Q

CH3CH2NH2 + H2SO4

A

(CH3CH2NH3+)2SO4 2-

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10
Q

forming a primary amine

A

ammonia reacts with a haloalkane, forming an ammonium salt

ammonium salt is mixed with aqueous alkali to generate the amine from the salt

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11
Q

how to form propylamine + sodium chloride

A

salt formation
1-chloropropane + HN3 -> propylammonium chloride (salt)

amine formation
propylammonium + NaOH -> propylamine

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12
Q

what are the conditions to form a primary amine?

A
  • ethanol is used as a solvent - this prevents substitution of the haloalkane by the water to produce alcohols
  • excess ammonia - reduces further substitution of the group to form secondary and tertiary amines
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13
Q

forming a secondary/tertiary amine

A

ammonia and a haloalkane react to form a primary amine- however this reaction isn’t pure as the primary amine can react further with a haloalkane to form a secondary amine.

-> you still need to react with NaOH to generate the mine from its salt

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14
Q

How to form Dipropylamine and NaCl-

A

CH3CH2CH2Cl + CH3CH2CH2NH2 -> (CH3CH2CH2)2NH2+Cl-
Propylamine -> Dipropylammonium chloride

(CH3CH2CH2)2NH2+Cl- + NaOH -> (CH3CH2CH2)2NH + NaCl + H2O

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15
Q

How to form Tipropylamine and NaCl-

A

CH3CH2CH2Cl +(CH3CH2CH2)2NH -> (CH3CH2CH2)2NH+Cl-
Propylamine -> Dipropylammonium chloride

((CH3CH2CH2)2NH+Cl- + NaOH -> (CH3CH2CH2)2N + NaCl + H2O

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16
Q

how to prepare an aromatic amine

A

reduction of nitrobenzene
heat under reflux with tin and HCl (reducing agent)
-> it forms the ammonium salt (phenylammonium)
react with excess NaOH
-> forms phenylamine

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17
Q

what is an amino acid?

A

organic compund containing both amine NH2 and carboxylic acid COOH functional groups
-> body has 20
R is a variable side chain

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18
Q

what is an alpha amino acid
give its general formula

A

the amine group is attached to the alpha carbon - the second carbon atom, next to the carboxylic group
RCH(NH2)COOH

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19
Q

what is a beta amino acid

A

where the amino acid is attached to the third carbon

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20
Q

amino acids with aqueous alkalis

A

amino acid react with an aqueous alkali to form a salt and water

21
Q

how do you esterify a amine acid

A

heat with alcohol in the presence of concentrated sulfuric acid

22
Q

what is an amide

A

the products of reactions of acyl chlorides with ammonia and amines

23
Q

primary amide

A

one carbon bonded to nitrogen

24
Q

what is an optical isomer

A

it is found in molecules that contain a chiral centre (carbon attached to 4 different atoms)

this means there are two molecules that are non-superimosable mirror image structures (enantiomers)

25
Q

what are two important condensation polymers?
give some starting materials

A
  • polyesters and polyamides
  • carboxylic acids and their derivatives are common starting materials
26
Q

what is condensation polymerisation

A

the joining of monomers with loss of a small molecule, usually water or HCl.

27
Q

what do you need for a condensation reaction

A

two functional groups

28
Q

what bond holds monomers in a polyesters

A

monomers are joined by ester linkages
O
∥
C — O

29
Q

two ways polyesters are made

A
  • made from one monomer containing both a carboxylic acid and an alcohol group
  • made from two monomers here one contains a two carboxylic acid groups and the other containing two alcohol groups
30
Q

two examples of polyesters made from two monomers with two functional groups groups

A
  • one monomer is a dial, with wo hydroxyl group
  • one monomer is a dicarboxylic acid with two carboxylic acid groups
31
Q

what is a polyamide

A

condensation polymers formed when monomers are joind by amide linkages in a long chain

32
Q

what is a amide linkage

A

O O
∥
——– C — N ——-
|
H

33
Q

how can polyamides be made

A
  • from one monomer containg both a COOH (or acyl chloride) and an amine group
  • from two monomers one containing two COOH (or acyl chlorides) and the other containing two amine groups
34
Q

(CH3)3CCHBrCH3 has stereoisomers.
Explain the term stereoisomers and name this type of stereoisomerism

A

Same structural formula
AND
Different arrangement (of atoms) in space
OR different spatial arrangement (of atoms)

optical

35
Q

bond angle of a primary amine

A

107- trigonal pyrmidal

36
Q

what is a amine group attached to benzene

A

phenylamine

37
Q

compare melting point of a primary amina and an alkane of a similar chain length

A
  • relatively high due to hydrogen bonding between molecules
    :N-H therefore h bonding

only true to primary, secondary and phenylamine

38
Q

Tm and Tb of primary amines compared to secondary

A

low due to no hydrogen bonds

39
Q

are amines soluble

A

yes

40
Q

producing amines from a haloalkane

A

nucleophilic substitution - where N is the nucleophile in excess to prevent further subs
primary : R-X + NH3 -> R -NH2 + HX
ethanol is needed
secondary : R-X + R-NH2 -> R-NH-R
tertiary: R-X + R-NH-R -> R-N(R)-R

41
Q

producing amines from nitriles

A

Reagents: LiAlH4 (ether) or H2 with Ni/Pt catalyst

R-CN + 2[H] -> R-C-NH2

reduction

42
Q

producing amines from nitrobenzene

A

Reagents: Conc HCL and SN catalyst followed by NaOH

Benzen-NO2 + 6[H] -> benzene-NH2 + 2H2O

product is phenylamine
HCl does the reducing- however it causes a salt forming as lone pair on N accepts
NaOH prevents the salt from forming as it neutralises excess H+

43
Q

amine in water

A

R-NH2 + H2O <=> R-NH3+ + OH-
forming an alkaline solution
lone pair on N accepts H+

44
Q

primary amine and HCl

A

R-NH2 + HCl -> R-NH3+ + Cl-
forms a salt _______ ammonium chloride

45
Q

ethylamine and nitric acid

A

C2H5NH2 + HNO3 -> C2H5NH3+ + NO3-

46
Q

why doe most amino acids have optical isomerism

A

central carbon atom has 4 different groups bonded to it (ie chiral)

47
Q

what is a zwitterion how does it affect properties

A

COOh of an amino acid donates H+ to the amine group. Lone pair on nitrogen accepts the H+. forming a positive and negative end - opositly charged poles so it is very soluble and a very high Tm (due to strong electrostatic attractions-like ionic substances)

overall it is uncharged

48
Q
A

Chemistry (30 decks)

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