Amines and polymers

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81 Terms

1
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If its a primary amine what does it look like?

<p></p>
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How to name amines?

-amine

e.g. methylamine

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<p>What is the name?</p>

What is the name?

ethylamine

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<p>What is the name?</p>

What is the name?

dimethlyamine

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<p>What is the name?</p>

What is the name?

phenylamine

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What does the nitrogen atom in amines accept?

proton H

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What do amines therefore act as?

Bases in aq solutions as they donate lone pair of electrons to proton in form of dative bond

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e.g. of ammonia + HCl

NH3 +HCl —> NH4+Cl-

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e.g. of how amine (C2H5NH2) react with HCl and what forms?

C2H5NH2 + HCl —> C2H5NH3+Cl-

amine salts e.g. ethylammonium chloride

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What is the solubility of amine salts?

soluble ionic compound

when alkyl group is small they are water soluble but become less so as carbon chain increases

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What are the ways amines can be prepared:

  • Reaction between hallogenoalkanes with ammonia

  • Reduction of nitriles

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What type of reaction is halogenoalkanes with ammonia?

Nucleophilic substitution in which lone pair in ammonia acts as nucleophile and replaces halogen in halogenoalkane

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What are the conditions needed for reaction of halogenoalkanes and ammonia?

Excess, hot ethanolic ammonia under pressure

—> primary amine

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e.g. of haloalkane with ammonia

knowt flashcard image
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What type of reaction is nitriles forming amines?

Nitriles contain a -CN group which is reduced to a -NH2

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Conditions for nitrile reduction?

nitrile vapour and hydrogen gas are passed over ni cat/ LiAlH4 in dry ether

—> primary amine

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e.g. of reduction of nitrile

knowt flashcard image
18
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What type of reaction is halogenoalkane with primary amine?

Nucleophilic substitution reaction in which nitrogen in primary amine acts as nucleophiles and replaces the halogen in the halogenalkane

19
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What conditions for halogenoalkanes with primary amine?

Primary amine in ethanol and heated in sealed tube under pressure a secondary amine is formed

20
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e.g. of reaction

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21
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How are tertiary amines formed?

further reaction of secondary amine

e.g. triethylamine (CH3CH2)N

22
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What is phenylamine?

organic compound made of benzene ring and amine (NH2) functional group

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What can be reduced to pheylamine, C6H5NH2?

Nitrobenzene, C6H5NO2

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Step 1:

Reduction of nitrobenzene:

  • Nitrobenzene, C6H5NO2, is reacted with tin and conc HCl (both act as reducing agents)

  • Reaction mixture is heated under reflux in boiling water bath

  • Phenylammonium ions, C6H5NH3+ are protonated due to the acidic conditions

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Step 2:

Formation of phenylamine:

  • phenylammonium ions, C6H5NH3+, are deprotonated by the addition of excess sodium hydroxide solution, NaOH (aq)

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Summary:

knowt flashcard image
27
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What functional group does amino acids have?

  • Basic amino (-NH2) group

  • Carboxylic acid (-COOH) group

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What can amino acids act as + what is this known as?

Act as both acids and bases

Amphoteric

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Amino acids make up _____

proteins

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What is the arrangment of 2-aminocarboxylic acids?

Type of amino acids in which amine (NH2) group is bonded to carbon atom next to COOH group

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General strucutral formula of amino acids:

RCH(NH2)COOH

R group can be acidic, basic or neutral

<p>RCH(NH<sub>2</sub>)COOH</p><p>R group can be acidic, basic or neutral </p>
32
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Reactions of amine group with acids- amino acids

Amine is basic and reacts with acids to make salts

e.g. amino acid reacts with HCl to form ammonium salt

<p>Amine is basic and reacts with acids to make salts </p><p>e.g. amino acid reacts with HCl to form ammonium salt </p>
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Reaction of carboxylic acid group with aqueous alkalis

  • Amino acid reacts with aq alkali to form salt and water

  • eg. general amino acid reacts with soidum hydroxide to form a sodium salt

<ul><li><p>Amino acid reacts with aq alkali to form salt and water </p></li><li><p>eg. general amino acid reacts with soidum hydroxide to form a sodium salt</p></li></ul><p></p>
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Reaction of carboxylic acid group in esterification with alcohols

conditions needed?

  • Amino acids are esterified by heating with alc in presence of conc sulphuric acid

  • Carboxylic acid group is esterified whilst basic amine group is protonated due to acidic conditions:

<ul><li><p>Amino acids are esterified by heating with <strong>alc in presence of conc sulphuric acid</strong></p></li><li><p>Carboxylic acid group is esterified whilst basic amine group is protonated due to acidic conditions:</p></li></ul><p></p>
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How are amides formed?

Condensation reaction with carboxylic acids or acyl chlorides with ammonia or amines

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General structure of amides

RCONR2

<p>RCONR<sub>2</sub> </p>
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term image
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What are primary, secondary and tertiary amides?

  • Primary amide - one carbon bonded to the amide nitrogen 

    • R' and R'' are both hydrogen atoms so one "ammonia" hydrogen has been substituted with the carbonyl group from the RCO portion of the molecule

  • Secondary amide - two carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)

  • Tertiary amide - three carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)

<ul><li><p>Primary amide - one carbon bonded to the amide nitrogen&nbsp;</p><ul><li><p>R' and R'' are both hydrogen atoms so one "ammonia" hydrogen has been substituted with the carbonyl group from the RCO portion of the molecule</p></li></ul></li><li><p>Secondary amide - two carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)</p></li><li><p>Tertiary amide - three carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)</p></li></ul><p></p>
39
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How to name primary amides?

add -amide to the stem

e.g. ethanamide

40
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Secondary amides:

  • secondary amides, the alkyl chain attached to the nitrogen is added at the start of the chemical name

  • This alkyl chain is prefixed with N-

  • The chain containing the carbonyl group is named the same as a primary amide

e.g. N-propylethanamide

<ul><li><p>secondary amides, the alkyl chain attached to the <strong>nitrogen</strong> is added at the start of the chemical name</p></li><li><p>This alkyl chain is prefixed with N-</p></li><li><p>The chain containing the carbonyl group is named the same as a primary amide</p></li></ul><p>e.g. N-propylethanamide</p>
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Naming tertiary amides:

  • naming of these chains is the same as secondary amides

  • As with standard nomenclature, these chains are listed in alphabetical order and the prefix 'di-' is used if necessary

  • N-methyl-N-propylethanamide

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What type of isomer is optical and other type?

Stereoisomerism:

Geometrical (E/Z)

Optical

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stereoisomers definition

molecules with same structural formula but atoms arranged differently in space

<p>molecules with same structural formula but atoms arranged differently in space </p>
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Compounds with a chiral centre (chiral molecules) exist as two optical isomers which are also known as _________

enantiomers

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enantiomers definition

non-superimposable mirror images of each other just like your left and right hand

<p><strong>non-superimposable</strong><span> </span><strong>mirror images </strong><span>of each other just like your left and right hand</span></p>
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chiral:

  • Whether a particular carbon is bonded to four different atoms or groups of atoms and therefore is chiral

  • Whether a particular carbon is bonded to two of the same atoms or groups of atoms and therefore cannot be chiral

47
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What are condensation polymers?

polymer is produced by repeated condensation reactions between monomers

condensation polymerisation involves the elimination of a small molecule

48
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Condensation polymers can be identified because the monomers are linked by _____

ester or amide bonds

49
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Condensation polymers can be formed by:

  • dicarboxylic acids and diols

  • dicarboxylic acids and diamines

  • amino acids

50
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How is polyester formed + what bond forms?

dicarboxylic acid monomers and diol monomers —> one of the -OH groups on the diol and the hydrogen atom of the -COOH are expelled as a water molecule (H2O)

ester bonds

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What polyester looks like?

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e.g. of polyester

poly(ethylene terephthalate) or PET/Terylene

53
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What PET looks like

knowt flashcard image
54
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Formation of polyesters - hydroxycarboxylic acids

hydroxycarboxylic acids

  • They contain an alcohol group (-OH) at one end of the molecule while the other end is capped by a carboxylic acid group (-COOH)

55
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What are polyamides?

polymers where repeating units are bonded together by amide links

formula of an amide group is -CONH

<p>polymers where repeating units are bonded together by amide links</p><p><span>formula of an amide group is -CONH</span></p>
56
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What forms polyamide?

diamine (contains 2 -NH2 groups) and a dicarboxylic acid (2 -COOH groups)

OR

Dioyl dichlorides (Contains 2 -COCl groups) instead of the acid (it is more reactive monomer but more expensive)

57
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What polyamides look like?

knowt flashcard image
58
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Formation of proteins- amino acids

proteins are made up from amino acid monomers

Amino acids have an aminocarboxylic acid structure

properties are governed by a branching side group - the R group

<p>proteins are made up from amino acid monomers </p><p>Amino acids have an aminocarboxylic acid structure</p><p><span>properties are governed by a branching side group - the R group</span></p>
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How are dipeptides formed?

polymerising 2 amino acids together

amine group (-NH2) and acid group (-COOH) of each amino acid is used to polymerise with another amino acid

<p><span>polymerising 2 amino acids together</span></p><p><span>amine group (-NH</span><sub>2</sub><span>) and acid group (-COOH) of each amino acid is used to polymerise with another amino acid</span></p>
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How are polypeptides formed?

polymerising more than 2 amino acids together

61
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Both polyesters and polyamides can be broken down using ____ + what is the advantage?

hydrolysis reactions- at landfill can be easily broken down and products used for other applications

advantage over polymers produced from using alkene monomers

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How is acidic hydrolysis done?

an acid (such as hydrochloric acid) acts as the catalyst

  • Polyamides such as Kevlar are heated with dilute acid

  • This reaction breaks the polyamide into a dicarboxylic acid and ammonium ions

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What is alkaline hydrolysis?

  • polyamide is heated with a species containing hydroxide ions (eg. sodium hydroxide)

  • This breaks the polymer into the sodium salts of its monomers (dicarboxylic acid salt and diamines)

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polyamide-hydrolysis

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Hydrolysis of polyesters:

  • Ester linkages can also be degraded through hydrolysis reactions

    • The acidic and alkaline hydrolysis of polyethylene terephthalate (PET) is shown below

  • Acid hydrolysis forms the diol and dicarboxylic acid that were used to form the polyesters

  • Alkaline hydrolysis forms the diol and dicarboxylic acid salt 

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haloalkane —> amine ( primary)

haloalkanes undergo nucleophilic substitution with ethanoic ammonia to form primary amine:

  1. RX + NH3 —> RNH2 + HX

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How do you reduce unwanted side reactions:

excess ammonia

as it deacreases probability of amine reacting with haloalkane rather than ammonia

RX + 2NH3 —> RNH2 +NH4X

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How is secondary amine formed?

knowt flashcard image
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What is another way to form amines?

reduction of nitriles

H2 + Ni cat

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What is a nitrile?

knowt flashcard image
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how to make aromatic amines

reduction of aromatic nitro- compound

using tin and conc HCl + reflux

equation is + 6(H) —> H20

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As phenylamine is basic what will happen

react with acid to produce ammonium ion can be converted to phenyl-amine by treatment with alkali

C6H5NH3 + OH- —> C6H5NH2 + H20

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How amines behave like bases

accept proton

lone pait on N donates a pair forming ammonium salt via datice cov bond

RNH2 + HNO3- —> RH3+ + NO3-

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What is alpha amino acid?

NH2 is attached to second carbon atom

2-AMINO ACIDS

<p>NH2 is attached to second carbon atom </p><p>2-AMINO ACIDS</p>
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Amino acid acting as acid in aq

H2NCHRCOOH + OH- —> H2NCHROO- + H20

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Amino acid acting as base in aq

H2NCHRCOOH + H+ —> H3N+CHRCOOH

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acidic condition for esterfication of amino acids are needed to ____

protonate amino group

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properties of enantiomers

  • identical chemical properties and same b.p and solubilities

  • have different biochemical reactions (react with enantiomers of other substance)

  • rotate the plane of polarisation of plane polarised light

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ammonium ion shape

tetrahedral

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ammonia shape

pyramidal