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Alevel Chemistry OCR A > Module 6: Amine, Chirality, Amino Acid, Nitriles, Amide > Flashcards

Module 6: Amine, Chirality, Amino Acid, Nitriles, Amide Flashcards

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1
Q

Amines
What is an amine

A

Organic compound derived from ammonia in which one or more h atoms has been replaced by a carbon chain or ring

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2
Q

Amines
What is the nitrogen attached to in an aromatic amine

A

Atleast one alkyl group

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3
Q

Amines
What is the nitrogen attached to in an aromatic amine

A

Directly attached to Aromatic ring

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4
Q

Amines
What are they classifies into

A

Primary secondary tertiary

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5
Q

Amines
Is ammonia an amine

A

No

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6
Q

Amines
General structure for primary

A

R-NH2

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7
Q

Amines
General structure for secondary

A

R-NH-R’

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8
Q

Amines
What is general structure for tertiary

A

R-NR’-R’’

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9
Q

Amines
How do you name primary amine where amine group on end of chain

A

Alkylamine

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10
Q

Amines
How do you name a primary amine where amine in middle of carbon chai.

A

2-aminealkane

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11
Q

Amines
How do you name a secondary or tertiary

A

N-alkyl-N-alkylamine etc

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12
Q

Amines
What can they act as

A

Bases and nucleophiles

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13
Q

Amines
Why can they act as bases

A

Can accept protons (lone pair on N)

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14
Q

Amines
What effect do the R groups have

A

Inducing effect as push electrons towards N atom

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15
Q

Amines
Which classification of amines are the strongest base and why

A

Has more inducing effect

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16
Q

Amines
What is the weakest base and why

A

Phenylamine amine as lone pair is partially delocalised so pulled away so less available to accept proton

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17
Q

Amines
What bond is formed when an amine accepts a proton

A

Dative covalent bond

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18
Q

Amines
What is produced in reaction with acid

A

Alkylammonium salt

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19
Q

Preparation of Amines
What is the single step method to pepare an primary amine

A

Nucleophilic substitution with ammonia

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20
Q

Preparation of Amines
What are the conditions for nucleophilic substitution with haloalkane

A

Excess Ethanoic ammonia, reflux

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21
Q

Preparation of Amines
What is produced in reaction haloalkane and excess ammonia

A

Primary amine + ammonium salt

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22
Q

Preparation of Amines
Mechanism

A

Need to know *

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23
Q

Preparation of Amines
Equation for reaction between chloroethane and NH3

A

CH3CH2Cl + NH3 —> CH3CH2NH2 + NH4+Cl-

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24
Q

Preparation of Amines
Why is ethanol used as solvent

A

To prevent substitution of the haloalkane by water to produce alcohols

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25
Q

Preparation of Amines
Why is excess ammonia used

A

Reduce further substitution of the amine group to form secondary and tertiary amines

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26
Q

Preparation of Amines
What can the primary amine formed now act as

A

A nucleophile to the haloalkane

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27
Q

Preparation of Amines
What does primary amine + halo alkane produce

A

Secondary amine + HCl

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28
Q

Preparation of Amines
How could a tertiary amine then be formed

A

Haloalkane + secondary alkane

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29
Q

Preparation of Amines
What is the two step preparation

A

Nucleophilic substitution between halo alkane and cyanide ion
Reduction of nitrile

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30
Q

Preparation of Amines
Reagents and conditions for halo alkane and cyanide

A

NaCN in ethanol , reflux

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31
Q

Preparation of Amines
Reaction between bromoethane and CN-

A

CH3CH2Br + CN- —> CH3CH2CN + BR-

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32
Q

Preparation of Amines
What is key in adding a cyanide group

A

Carbon chain is extended

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33
Q

Preparation of Amines
Why is there high electron density in CN

A

Unsaturated bond with electrons which are localised

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34
Q

Preparation of Amines
Reagent or condition for nitrile to amine

A

2 H2, Ni catalyst
/4 [H]

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35
Q

Preparation of Amines
What types or reaction is nitirle to amine

A

Reduction.
Electrophilic addition
Hydrogenation

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36
Q

Preparation of Amines
Why might the 1 step method be preferred

A

Less energy required as only one step

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37
Q

Preparation of Amines
Why may the 2 step method be proffered

A

Further substitution doesnt occur

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38
Q

Preparation of phenyl amine
How many steps required from benzene

A

2

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39
Q

Preparation of phenyl amine
Why can’t ammonia just be used

A

Ammonia is a nucleophiles whereas benzene undergoes reactions with electrophiles

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40
Q

Preparation of phenyl amine
Conditions for benzene to nitrobenzene

A

Conc H2SO4
conc HNO3
50’C

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41
Q

Preparation of phenyl amine
Type or reaction for benzene to nitrobenzene

A

Electrophilic substitution

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42
Q

Preparation of phenyl amine
Conditions and reagent for nitrobenzene to phenyl amine

A

Tin, conc HCl, reflux
Then NaOH(aq)

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43
Q

Preparation of phenyl amine
What type of reaction is nitrobenzene to phenyamine

A

Reduction

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44
Q

Preparation of phenyl amine
Equation for nitrobenzene to Phenylamine

A

C6H5NO2 + 6[H] —> C6H5NH2 + 2 H2O

45
Q

Chirality
What type of isomerism are optical isomers

A

Stereoisomerism

46
Q

Chirality
Deifntion for optical isomers (3)

A

Molecule which contains a chiral centre and has non superimposable mirror images where each one rotates a plane of polarised light in opposite directions

47
Q

Chirality
When does optical isomerism occur

A

When there is a chiral centre

48
Q

Chirality
When is there a chiral carbon

A

Asymmetric carbon atom with four different groups and no double bond

49
Q

Chirality
How do you draw two optical isomers

A

Draw molecule in 3D plane
Draw mirror line
Draw reflected 3D molecule

50
Q

Chirality
What are optical isomers also known as

A

Enantiomers

51
Q

Amino acids
What would functional groups do they contain

A

Amine and carboxylic acid

52
Q

Amino acids
When is an amino acid alpha

A

When both functional groups and a H atom are attached to the same group

53
Q

Amino acids
What is the general formula for an alpha amino acid

A

RCH(NH2)COOH

54
Q

Amino acids
What two properties do they have

A

Acidic and basic properties

55
Q

Amino acids
What is a zw itter ion

A

When proton from COOH groups is donated to NH2 to form a dipolar ion

56
Q

Amino acids
What is the isoelectric point

A

Specific pH are you which the zwitter ion is formed from amino acid

57
Q

Amino acids
What state are they in neutral ph

A

Basic non charged compound

58
Q

Amino acids
What happens at Isoelectric point

A

Zwitter ion formed with Positve NH3 and negative COO-

59
Q

Amino acids
What happens at a ph higher then the isoelectric point

A

The NH2 group stays neutral but COO- has charge

60
Q

Amino acids what happens at ph lower then the islelectric point

A

COOH group stays neutral whereas the NH3+ has charge

61
Q

Amino acids
What type of isomer can they form

A

Optical isomers

62
Q

Amino acids
Why do they form optical isomers

A

Have a chiral carbon with four different groups -COOH, -NH2, -R, -R’(H)

63
Q

Amino acids
How many optical isomers are formed

A

Two

64
Q

Amino acids
Which amino acid has no optical isomerism and why

A

Glycine as had two H atoms

65
Q

Amino acids
How are zwitter ions formed

A

Proton from COOH groups moves to NH2

66
Q

Amino acids
Why do zwitter ions have higher melting and boiling points

A

Produces increased intermolecular forces due to charge

67
Q

Amino acids
Why are amino acids bifunctional

A

Have two functional groups one which can act as a base and one which can act as acid

68
Q

Amino acids
Which funtion al group an act as a base

A

NH2

69
Q

Amino acids
Which functional group can act as an acid

A

COOH

70
Q

Amino acids
Equation for reaction with H+

A

HOOCCH(R)NH2 + H+ —> HOOCCH(R)NH3+

71
Q

Amino acids
Equation for reaction with HCl

A

HOOCCH(R)NH2 + HCl —> HOOCCH(R)NH3+Cl-

72
Q

Amino acids
Equation for reaction with OH-

A

HOOCCH(R)NH2 + OH- —> -OOCCH(R)NH2 + H2O

73
Q

Amino acids
Equation for reaction with NaOH

A

HOOCCH(R)NH2 + NaOh —> Na+ -OOCCH(R)NH2 + H2O

74
Q

Reactions of Amino acids
What do you have to be careful of with reactions

A

That R chain wont also react with it

75
Q

Reactions of Amino acids
What is formed when reacted with NaOH

A

Salt + water
COO-Na+

76
Q

Reactions of Amino acids
What is formed when reacted with HCl

A

Salt
NH3+Cl-

77
Q

Reactions of Amino acids
What happens when reacted with alcohol and what conditions needed

A

Esterification
Conc H2SO4

78
Q

Reactions of Amino acids
What is produced when reacted with alcohol with conc H2SO4

A

Ester + water
C(=O)OC

79
Q

Reactions of Amino acids
What happens when reacted with another amino acid

A

Form a condensation polymer

80
Q

Reactions of Amino acid
What formed when reaction wih Acyl chloride

A

Amide bond + HCl
NH-C(=O)C

81
Q

Amides
What funtional group do they have

A

-CONH2

82
Q

Amides
Why do they behave differently from amines

A

Carbonyl group pulls electrons away from rest of -CONH2 group

83
Q

Amides
How can they be classified

A

Primary or secondary depending on how many hydrogens the nitrogen atom is bonded to

84
Q

Preparation of Amides
How can they be formed from carbonxykic acid and what if formed equation

A

Carboxylic acid + amine —> amide + water

85
Q

Preparation of Amides
What type of reaction is carboxylic acid + amine

A

Condensation

86
Q

Preparation of Amides
How can they be prepared from acid anhydride equation

A

Acid anhydrides + ammonia —> amide + carboxylic acid

87
Q

Preparation of Amides
How can they be prepared from Acyl chlorides equation

A

Acyl chloride + amine —> amide + HCl/NH4Cl

88
Q

Reactions of Amides
What does it undergo

A

Hydrolysis

89
Q

Reactions of Amides
What is hydrolysis

A

Splitting a compound using water

90
Q

Reactions of Amides
What two types of hydrolysis do they undergo

A

Acidic
Alkaline

91
Q

Reactions of Amides
What is needed for acidic hydrolysis

A

Heating with dilute acid

92
Q

Reactions of Amides

Reactions of Amides
What is formed in acidic hydrolysis

A

Carboxylic acid and ammonium salt

93
Q

Reactions of Amides
Equation for N-ethylpropanamide with HCL

A

CH3CH2CONHCH2CH3 + HCl(aq) —H2O—> CH3CH2COOH + CH3CH2NH3Cl

94
Q

Reactions of Amides
What is needed for alkaline hydrolysis

A

Heat with sodium hydroxide

95
Q

Reactions of Amides
What is formed in the alkaline hydrolisis

A

Carboxylate salt and amine

96
Q

Reactions of Amides

Reactions of Amides
Equation for N-ethylethanamide and NaOH

A

CH3CH2CONHCH2CH3 + H2O —NaOH(aq) —> CH3CH2COO-Na+ + CH3CH2NH2

97
Q

polymers
What are the two p types of polymers

A

Addition
Condensation polymers

98
Q

polymers
What are addition polymers a and how are the formed

A

Long chain molecules made from joining together many shorter molecules(monomers) together to form a long chain molecule

99
Q

polymers
What are the monomers for addition polymers

A

Alkenes or moleucles with C=C bonds

100
Q

polymers
Why are addition polymers bad for they environment

A

Non biodegradable due to absence of polar bonds in the main chain (all C-C bonds)

101
Q

polymers
What is atom economy like for addition polymers

A

100%

102
Q

polymers
What are condensation polymers and how are they formed

A

Long chain molecules made from joining together many shorter molecules (monomers ) together to form a long chain molecule with water also formed

103
Q

Condensation polymers
What are the monomers

A

Di carboxylic acids a with diols
Di carboxylic acids with diamines
Amino acids
Compound containing an amine and carboxylic acid functional group

104
Q

Condensation polymers
Two examples

A

Polyesters
Polyamides

105
Q

Condensation polymers
Wat is a polyamide

A

When Di carboxylic acid reacts with Di amine polyamide formed and water released

106
Q

Condensation polymers
How do you show one repeating unit

A

Open bonds at either end (…—…)

107
Q

Condensation polymers
How do you show the polymer structure

A

Square brackets with bond at either end with one repeating unit
N at end to show large number

108
Q

Condensation polymers
What is a polyester

A

When Di carboxylic acid react with a diol forms poly ester and water is released

Alevel Chemistry OCR A (14 decks)

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