Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

Advanced higher chemistry > Synthesis - organic > Flashcards

Synthesis - organic Flashcards

You may prefer our related Brainscape-certified flashcards:
Periodic Table flashcards Chemistry 101 flashcards AP® Chemistry flashcards Organic Chemistry 101 flashcards
1
Q

Bond fission

A

Where bonds are broken in a chemical reaction

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

Types of bond fission

A

Homolytic + heterolytic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

Why are free radicals unsuitable for synthesis

A

Because free radical reactions form complex mixtures of products.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

Free radical reaction stages

A

Initiation
Propagation
Termination

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

Initiation

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Termination

A

Where two free radicals bond forming a stable molecule.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

When does heterolytic fission occur

A

When the bond between atoms is a polar covalent bond.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Why is heterolytic fission suitable for synthesis

A

Heterolytic fission results in fewer products.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Haloalkanes types

A

Primary , secondary and tertiary

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Haloalkanes

A

A halogen bonded to an alkane at a hydrogen.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

What type of reaction is undergone by monohaloalkanes

A

Nucleophilic substitutions

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

Formation of alcohol from haloalkane

A

KOH + haloalkanes —> alcohol + KCl

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

Formation of ether from haloalkane

A

CH3O- + haloalkane —> ether + ionic substance

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
21
Q

Ether

A

A molecule with C-O-C

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
22
Q

Formation of carboxylic acid from haloalkane

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
23
Q

Acid hydrolysis

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
24
Q

Types of reaction mechanism

A

SN1
SN2

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
25
Q

SN1 stands for

A

First order nucleophilic substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
26
Q

SN2 stands for

A

Second order nucleophilic substitution

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
26
Q

When does SN1 occur

A

When the haloalkane is tertiary

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
27
Q

When does SN2 occur

A

When the haloalkane is primary

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
28
Q

SN1 step 1

A

Tertiary haloalkane —> carbocation +halogen ion.
Heterolytic fission

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
29
Q

SN1 step 2

A

Carbocation + OH- —-> tertiary alcohol

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
30
Q

SN2 step 1

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
32
Q

Features of SN2

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions