Name the following molecules: CH3NH2 C2H5NH2 CH3CH2CH2NH2 What type of molecule are they?

Methylamine Ethylamine 1-aminopropane/propylamine Primary amines

Name CH3CH(NH2)CH3 What type of molecule is it?

2-aminopropane / methyl ethylamine Primary amine

Name CH3NHCH3 What type of molecule is it?

Dimethylamine Secondary amine (2 Hs replaced by alkyl groups)

Name CH3N(CH3)CH3 What type of molecule is it?

Trimethylamine Tertiary amine (3 Hs replaced by alkyl groups)

Name the following molecules: NH2CH2CH2NH2 NH2CH2CH2CH2CH2CH2CH2NH2 What type of molecule are they both?

Ethanediamine 1,6-diamino-hexane Diamines

Why do amines have the following properties? Soluble in water Act as bases

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

PL lnop: Amines, amides, acyl chlorides, nylons Flashcards by isabella rotheram

What are amines?

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

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Name the following molecules:
- CH₃NH₂
- C₂H₅NH₂
- CH₃CH₂CH₂NH₂
What type of molecule are they?

Methylamine
Ethylamine
1-aminopropane/propylamine
Primary amines

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Name CH₃CH(NH₂)CH₃
What type of molecule is it?

2-aminopropane / methyl ethylamine
Primary amine

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Name CH₃NHCH₃
What type of molecule is it?

Dimethylamine
Secondary amine (2 Hs replaced by alkyl groups)

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Name CH₃N(CH₃)CH₃
What type of molecule is it?

Trimethylamine
Tertiary amine (3 Hs replaced by alkyl groups)

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Name NH₂CH₂NH₂
What type of molecule is it?

Methanediamine
Diamine

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Name the following molecules:
- NH₂CH₂CH₂NH₂
- NH₂CH₂CH₂CH₂CH₂CH₂CH₂NH₂
What type of molecule are they both?

Ethanediamine
1,6-diamino-hexane
Diamines

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Why do amines have the following properties?

Soluble in water
Act as bases

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

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

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

Amines act as H⁺ acceptors

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

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

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

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

CH₃CH₂NH_{2 (aq)} + H₃O⁺_(aq) → CH₃CH₂NH₃⁺_(aq) + H₂O_(l)

Ethylamine + hydronium ion → ethylammonium ion + water

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What are primary amides?
Give their general formula
Draw their general structural formula

Carboxylic acid derivatives where the OH group is substituted by NH₂
RCONH₂

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How do you name primary amides?
Name CH₃CONH₂

Replace the “e” on the end of the alkane with “amide”
Ethanamide

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What are secondary amides?
Give their general formula
Draw their general structural formula

Carboxylic acid derivatives where the OH group is replaced by NHR’
RCONHR’

How do you name secondary amides?
Name CH₃CONHCH₃

RCONH₂R’
Name in format: N-R’ Ramide, i.e. N-_yl _amide
N-methyl ethanamide

What are acyl chlorides?

Give their general formula.

Carboxylic acid derivatives where the OH is substituted for chlorine.

RCOCl or C_nH_2n+1COCl

Name this molecule.

Ethanoyl chloride

Name this molecule:

CH₃CH₂CH₂COCl

Butanoyl chloride

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

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

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

Draw: nucleophilic substitution

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

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

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

What type of molecule is formed when acyl chlorides react with amines?
What mechanism occurs?
What type of reaction occurs?

Secondary amide
Nucleophilic substitution
Condensation reaction

Acyl chlorides react vigorously with alcohols. * What type of mechanism occurs? * What is produced? * What type of reaction occurs?

* Nucleophilic substitution * Esters (RCOCl + R'OH → RCOOR' + HCl) * Condensation reaction

* What are polyamides? * What is the other name for them?

* Polymers where monomer links are secondary amide groups * Nylons

* In what 2 ways can polyamides be made? * Which method is quicker?

* 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 ## Footnote * Diacyl dichloride = symmetrical molecules where both ends are COCl* * Stability in solution: Cl^- ions \> carboxylate ions \> OH^- ions*

* 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?

* Both molecules have reactive groups in 2 places (amine and carboxyl) * Condensation polymerisation * A polyamide (nylon)

How are nylons named?

* 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

* Write an equation to show the polymerisation of 1,6-diaminohexane and decanedioyl chloride * Name the polymer formed

* Name this polymer * Explain how it was formed --(NH(CH₂)₅CO)--_n

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

Name the mechanism that occurs during: * Condensation polymerisation * Addition polymerisation

* Nucleophilic substitution * Electrophilic addition

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

Draw a mechanism representing the formation of polypropene.