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Synthesis - organic Flashcards

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1
Q

Bond fission

A

Where bonds are broken in a chemical reaction

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2
Q

Homolytic fission definition

A

When a covalent bond breaks and each atom gets one electron from the former bond meaning free radicals are formed.

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3
Q

Types of bond fission

A

Homolytic + heterolytic

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4
Q

Why are free radicals unsuitable for synthesis

A

Because free radical reactions form complex mixtures of products.

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5
Q

Free radical reaction stages

A

Initiation
Propagation
Termination

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6
Q

Initiation

A

A stable molecule breaks down into two free radicals under UV.

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7
Q

Propagation

A

Where a free radical bonds with a stable and forms a free radical and a stable. Then this happens again forming the original free radical.

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8
Q

Termination

A

Where two free radicals bond forming a stable molecule.

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9
Q

Arrows in free radical reactions

A

Initiation: arrow goes away from both stable atoms.
Propagation: free radical towards stable, stable towards free radical, stable away from free radical.
Termination: free radicals towards each other.

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10
Q

Heterolytic fission

A

Where a covalent bond breaks and one atom retains both electrons from the covalent bond, meaning oppositely charged ions are formed.

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11
Q

When does heterolytic fission occur

A

When the bond between atoms is a polar covalent bond.

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12
Q

Why is heterolytic fission suitable for synthesis

A

Heterolytic fission results in fewer products.

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13
Q

Homolytic versus heterolytic fission

A

Homolytic forms free radicals
Heterolytic forms ions
Homolytic is suitable for synthesis
Heterolytic is unsuitable for synthesis
Homolytic occurs with non polar bonds
Heterolytic occurs when bonds are polar.

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14
Q

Haloalkanes types

A

Primary , secondary and tertiary

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14
Q

Haloalkanes

A

A halogen bonded to an alkane at a hydrogen.

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15
Q

What type of reaction is undergone by monohaloalkanes

A

Nucleophilic substitutions

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15
Q

Nucleophile definition

A

A chemical species which is an electron rich, negatively charged ion containing a non bonding electron pairs that it donates to form dative bonds.

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16
Q

Electrophile

A

A chemical species which is electron deficient and a positively charged ion which receives non bonding electron pairs from a nuleophile forming a dative bond.

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17
Q

Carbon halogen bond properties in haloalkanes

A

Carbon halogen bonds are polar and the carbon is delta positive and halogen is delta negative, this makes the carbon susceptible to nucleophilic attack.

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18
Q

Nucleophilic attack

A

Where a nuleophile bonds with a delta positive atom involved in a polar covalent bond by pushing out the delta negative atom.

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19
Q

Formation of alcohol from haloalkane

A

KOH + haloalkanes —> alcohol + KCl

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20
Q

Formation of ether from haloalkane

A

CH3O- + haloalkane —> ether + ionic substance

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21
Q

Ether

A

A molecule with C-O-C

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22
Q

Formation of carboxylic acid from haloalkane

A

Haloalkane + CN- ——> nitrile alkane
Nitrile alkane + H2O/H+—-> carboxylic acid

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23
Q

Acid hydrolysis

A

Where H2O/H+ is added to an alkane nitrile and forms a carboxylic acid

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24
Q

Types of reaction mechanism

A

SN1
SN2

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25
Q

SN1 stands for

A

First order nucleophilic substitution

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26
Q

SN2 stands for

A

Second order nucleophilic substitution

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26
Q

When does SN1 occur

A

When the haloalkane is tertiary

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27
Q

When does SN2 occur

A

When the haloalkane is primary

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28
Q

SN1 step 1

A

Tertiary haloalkane —> carbocation +halogen ion.
Heterolytic fission

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29
Q

SN1 step 2

A

Carbocation + OH- —-> tertiary alcohol

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30
Q

SN2 step 1

A

Primary haloalkane —> negative ion intermediate —-> primary alcohol

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31
Q

Features of SN1

A

The tertiary haloalkane will have more steric hinderance which means there isn’t enough space for the attacking nucleophile.

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32
Q

Features of SN2

A

The primary carbocation is less stable than the tertiary carbocation and therefore more unlikely to form.

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33
Q

Carbocation

A

A carbon molecule with a positive charge which a nuleophile will bind with

34
Q

Steric hindrance

A

Where there is a large bulk of non polar atoms on the molecule.

35
Q

Reagent of alcohol formation in nucleophilic substitution

A

KOH

36
Q

Solvent of alcohol formation in nucleophilic substitution

A

Water (H2O)

37
Q

Reagent for ether formation in nucleophilic substitution

A

KCH3O
K+(CH3O)-

38
Q

Solvent for ether formation

A

ethanol

39
Q

Process for producing carboxylic acid from haloalkane

A

Haloalkane reacts with cyanide ions (solvent ethanol) to form nitrile.
Nitrile reacts with H+/H2O to form carboxylic acid.

40
Q

Nucleophile charge

A

Negative (similar to ligands)

41
Q

Electrophile charge

A

Positive

42
Q

Arrows on SN1

A

In stage 1 double head arrow to halogen
In stage 2 double head arrow towards carbocation

43
Q

Arrow heads for SN2

A

Double head arrow to carbon in centre.

44
Q

SN1 mechanism kinetics

A

1st order overall nucleophilic substitution

45
Q

SN2 mechanism kinetics

A

2nd order overall nucleophilic substitution

46
Q

Alcohols melting and boiling points

A

Higher than other homologous series due to hydrogen bonding in the hydroxyl group.

47
Q

Alcohols solubility rule

A

Short chain alcohols are soluble in water, as the chain length increases the solubility decreases due to non polar bonds.

48
Q

Methods of alcohol preparation

A

Acid hydration of Alkenes
Reduction of aldehydes and ketones using lithium aluminium hydride
Nucleophilic substitution of haloalkanes.

49
Q

Lithium aluminium hydride

A

Li+[AlH4]-

50
Q

Alcohol condensation

A

Alcohol + carboxylic acid - -> ester + water

51
Q

Ester naming rule

A

Alcohol becomes branch, carboxylic acid or acid chloride becomes branch.

52
Q

Condensation of alcohol by more effective method

A

Alcohol + acid chloride —> ester + HCl

53
Q

Acid chloride

A

A carboxylic acid with Cl instead of OH

54
Q

Alcohols primary oxidation

A

Aldehyde then carboxylic acid

55
Q

Alcohols secondary oxidation

A

Ketone

56
Q

Alcohols dehydration

A

Alcohol —->Alkene
Concentrated sulphuric acid or phosphoric acid catalyst.
Lithium aluminium hydride

57
Q

Alcohol reaction with alkali metals

A

Alcohol + alkali metal —.> metal alkoxide + Hydrogen
Ch3OH + Na - > CH3ONa + H2

58
Q

Ether naming formula

A

Alkoxy - main chain.

59
Q

Ethers physical properties

A

Lack of hydrogen bonding will decrease mp + bp and decrease solubility in water.

60
Q

Elimination reaction

A

A reaction where a small molecule is removed from another molecule.

61
Q

Elimination reaction reagent (alcohol)

A

KOH

62
Q

Elimination reaction solvent

A

Ethanol

63
Q

Alkenes mechanism

A

Electrophilic addition

64
Q

Markovnikov’s rule

A

During addition of an alkene the hydrogen will bind to the carbon with more hydrogens bonded.

65
Q

Hydrohalogenation process

A

Double arrow from alkene double bond to delta positive hydrogen
Double arrow from bond to delta negative halogen.
Bromine nucleophile arrow to positive carbocation.

66
Q

Acid catalysed hydration process

A

Double arrow from double bond on alkene to H+
Carbocation intermediate formed with markovnikovs rule.
Water arrow to positive carbocation to form positive oxygen ion
Hydrogen oxygen bond arrow to oxygen.

67
Q

Halogenation mechanism

A

Di-halogen molecule will become temporarily delta positive and negative
Arrow goes from double bond to delta positive halogen
Arrow from halogen bond to delta negative bond.
Forms a triangle structure with bromine and bromine nucleophile.
Arrow to positive bromine ion
Arrow from bromine nucleophile to carbon.

68
Q

Oxidation of aldehydes

A

Carboxylic acid

69
Q

Oxidation of ketones

A

None

70
Q

Oxidising agents for carbonyl compounds

A

Fehlings solution
acidified dichromate ions
Tollens reagent

71
Q

Reducing agent for carbonyl compounds

A

Lithium aluminium hydride

72
Q

Preparation of carboxylic acids

A

Primary alcohols and aldehydes oxidation
Hydrolysis of esters
Acid hydrolysis of nitriles

73
Q

Carboxylic acid reaction with metal and base

A

Carboxylic acid + base - - salt + water
Carboxylic acid + metal makes salt + hydrogen

74
Q

Amines

A

Molecules with NH2 functional group

75
Q

Primary secondary and tertiary amine

A

The nitrogen is bonded to 1 2 or 3 carbons

76
Q

Amines physical properties

A

Higher mp and bp due to hydrogen binding in primary and secondary amines
The solubility of amines that are primary and secondary in water is also higher.

77
Q

PH of amines explanation

A

The line pair on the nitrogen allows for dative covalent binds to be formed with H+ ions, which shifts the water equilibrium to produce OH- ions

78
Q

Amines reaction with inorganic acid

A

Acid + amine —-> ionic compound
CH3NH2 + HCl —> CH3NH3+CL-

79
Q

Amines reaction to form amides

A

Amine + carboxylic acid —> ammonium salt + carboxylic ion —-> amides

80
Q

Benzene structural formula

A

C6H6
Alternating single and double carbon bonds

81
Q

Benzene bonding and reactions explanation

A

Benzene has sp2 hybridisation which allows for delocalised π electrons. This means it resists electrophiclic addition.
Benzene does undergo electrophilic substitution by replacing hydrogen with other molecules due to the polarity of the bond.

82
Q

Electrophilic substitution process

A

Cl2 + AlCl3 —-> Cl+ + [AlCl4]-
Cl+ + benzene —-Chlorobenzene

83
Q

Alkylation process

A

RCl + AlCl3 —-> R+ + [AlCl4]-
R+ + benzene —-> R benzene

84
Q

Nitration

A

Electrophilic substitution of benzene when a nitronium ion is used
nitric and sulphuric acid are used
HNO3 + 2H2SO4 - -> 2HSO4- + H3O+NO2+

85
Q

Sulphonation

A

Electrophilic substitution of benzene when a sulphonium ion is used.
Conc sulphuric acid is used
H2SO4 + H2SO4 —> H2O + HSO4- HOSO2+
Sulphonium ions + benzene —-> sulphonium benzene

Advanced higher chemistry (8 decks)

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