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chemistry > PL lnop: Amines, amides, acyl chlorides, nylons > Flashcards

PL lnop: Amines, amides, acyl chlorides, nylons Flashcards

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1
Q

What are amines?

A

Ammonia where at least one hydrogen is substituted for an alkyl group.

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2
Q
  • Name the following molecules:
    • CH3NH2
    • C2H5NH2​
    • CH3CH2CH2NH2
  • ​What type of molecule are they?
A
  • Methylamine
  • Ethylamine
  • 1-aminopropane/propylamine
  • Primary amines
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3
Q
  • Name CH3CH(NH2)CH3
  • What type of molecule is it?
A
  • 2-aminopropane / methyl ethylamine
  • Primary amine
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4
Q
  • Name CH3NHCH3
  • What type of molecule is it?
A
  • Dimethylamine
  • Secondary amine (2 Hs replaced by alkyl groups)
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5
Q
  • Name CH3N(CH3)CH3
  • What type of molecule is it?
A
  • Trimethylamine
  • Tertiary amine (3 Hs replaced by alkyl groups)
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6
Q
  • Name NH2CH2NH2
  • What type of molecule is it?
A
  • Methanediamine
  • Diamine
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7
Q
  • Name the following molecules:
    • NH2CH2CH2NH2
    • NH2CH2CH2CH2CH2CH2CH2NH2
  • What type of molecule are they both?
A
  • Ethanediamine
  • 1,6-diamino-hexane
  • Diamines
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8
Q

Why do amines have the following properties?

  • Soluble in water
  • Act as bases
A
  • Nitrogen atom has a lone pair of electrons
  • So amines can engage in hydrogen bonding with water
  • Lone pair accepts H+, forming a dative covalent bond

Bonding around N similar to that of ammonia

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9
Q

Explain why amines with longer alkyl groups are less soluble in water.

A

​(For larger alkyl groups:)

Enthalpy change of breaking water-water hydrogen bonds >

enthalpy change of forming intermolecular forces between alkyl group + water

and hydrogen bonds between water + lone pair on N

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10
Q

Give the equation for the reaction between 2-aminopropane and water.

A

CH3CH(NH2)CH3 + H2O → CH3CH(NH3+)CH3 + OH-

Amines act as H+ acceptors

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11
Q

Explain why amines react more strongly with acids than with water.

A
  • Lone pair on N partakes in dative covalent bonding, accepting a H+ (acting as a base)
  • H3O+ ions are more powerful proton donors than water
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12
Q

Write the equation for the reaction of 2-aminopropane and hydrochloric acid.

A

CH3CH(NH2)CH3 + HCl → CH3CH(NH3+Cl-)CH3

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13
Q

Write the symbol and word equation for the reaction of ethylamine with an acid.

A

CH3CH2NH2 (aq) + H3O+(aq) → CH3CH2NH3+(aq) + H2O(l)

Ethylamine + hydronium ion → ethylammonium ion + water

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14
Q
  • What are primary amides?
  • Give their general formula
  • Draw their general structural formula
A
  • Carboxylic acid derivatives where the OH group is substituted by NH2
  • RCONH2
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15
Q
  • How do you name primary amides?
  • Name CH3CONH2
A
  • Replace the “e” on the end of the alkane with “amide”
  • Ethanamide
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16
Q
  • What are secondary amides?
  • Give their general formula
  • Draw their general structural formula
A
  • Carboxylic acid derivatives where the OH group is replaced by NHR’
  • RCONHR’
17
Q
  • How do you name secondary amides?
  • Name CH3CONHCH3
A
  • RCONH2R’
  • Name in format: N-R’ Ramide, i.e. N-_yl _amide
  • N-methyl ethanamide
18
Q

What are acyl chlorides?

Give their general formula.

A

Carboxylic acid derivatives where the OH is substituted for chlorine.

RCOCl or CnH2n+1COCl

19
Q

Name this molecule.

A

Ethanoyl chloride

20
Q

Name this molecule:

CH3CH2CH2COCl

A

Butanoyl chloride

21
Q

All of the reactions below occur via the same mechanism. Using an amine and acyl chloride, draw the mechanism. State what it is called.

  • Amines + acyl chlorides
  • Amides + acyl chlorides
  • Alcohols + acyl chlorides
  • Carboxylic acids + acyl chlorides
  • Condensation polymerisation, forming:
    • Polyesters
    • Polyamides (nylons)
    • Polypeptides
A

Could include intermediate step in which H donates pair of electrons to N+ in NH3, so that it then deprotonates

22
Q

Write an equation for the reaction between 2-aminopropane and ethanoyl chloride.

A

Draw: nucleophilic substitution

CH3CH(NH2)CH3 + CH3COCl → CH3CONH(CH3)2 + HCl

23
Q

Suggest and explain which of amines and amides react with acyl chlorides.

A
  • Would react by nuc attack of δ+ carbon in acyl chloride
  • Amines react. Amides do not because C=O group pulls e- away, making them poorer nucleophiles
24
Q
  • What type of molecule is formed when acyl chlorides react with amines?
  • What mechanism occurs?
  • What type of reaction occurs?
A
  • Secondary amide
  • Nucleophilic substitution
  • Condensation reaction
25
Q

Acyl chlorides react vigorously with alcohols.

  • What type of mechanism occurs?
  • What is produced?
  • What type of reaction occurs?
A
  • Nucleophilic substitution
  • Esters (RCOCl + R’OH → RCOOR’ + HCl)
  • Condensation reaction
26
Q
  • What are polyamides?
  • What is the other name for them?
A
  • Polymers where monomer links are secondary amide groups
  • Nylons
27
Q
  • In what 2 ways can polyamides be made?
  • Which method is quicker?
A
  • Diamine + either dicarboxylic acid or diacyl dichloride
  • Diacyl chlorides react more quickly because Cl- is stabler in solution than OH-, so is better leaving group

  • Diacyl dichloride = symmetrical molecules where both ends are COCl*
  • Stability in solution: Cl- ions > carboxylate ions > OH- ions*
28
Q
  • Explain why 1,6-diaminohexane and hexanedioic acid can undergo polymerisation
  • Which type of polymerisation would occur?
  • Draw the repeating unit for this polymer
  • What type of polymer is this?
A
  • Both molecules have reactive groups in 2 places (amine and carboxyl)
  • Condensation polymerisation
  • A polyamide (nylon)
29
Q

How are nylons named?

A
  • According to the number of carbons in monomers
  • If one monomer with 6 Cs was used, it would be nylon-6
  • If two monomers, with 5 and 6 Cs, were used, it would be nylon-5,6
30
Q
  • Write an equation to show the polymerisation of 1,6-diaminohexane and decanedioyl chloride
  • Name the polymer formed
A
31
Q
  • Name this polymer
  • Explain how it was formed

–(NH(CH2)5CO)–n

A
  • Nylon-6
  • Made from a single monomer containing both an amine and COOH / COCl group: nH2N(CH2)5COOH / nH2N(CH2)5COCl
32
Q

Name the mechanism that occurs during:

  • Condensation polymerisation
  • Addition polymerisation
A
  • Nucleophilic substitution
  • Electrophilic addition
33
Q

Draw the repeating unit of the polymer that can be obtained from 3-aminobenzoic acid.

A
34
Q

Draw a mechanism representing the formation of polypropene.

A

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