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IB Chemistry SL > Topic 10: Organic Chemistry > Flashcards

Topic 10: Organic Chemistry Flashcards

1
Q

What is Organic Chemistry?

A

The study of carbon-based compounds.

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2
Q

What is a homologous series?

A

A series of compounds of the same family, with the same formula, differing by CH2.

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3
Q

What is the general formula of an alkane?

A

CnH2n+2

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4
Q

What is the general formula of an alkene?

A

CnH2n

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5
Q

What is the general formula of an alkyne?

A

CnH2n-2

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6
Q

What is the general formula of an alkyl?

A

CnH2n+1 (Hydrogen on an end of the hydrocarbon replaced with another group)

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7
Q

What is the general formula of a hydroxyl?

A

CnH2n+1OH

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8
Q

What is the general formula of an aldehyde?

A

CnH2nO

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9
Q

What is the general formula of a ketone?

A

CnH2nO

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10
Q

What is the general formula of a halogenoalkanes?

A

CnH2n+1X (where X is the halogen)

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11
Q

If a homologous group shares a functional group, what else do members of these group share?

A

Similar physical and chemical properties

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12
Q

What is the trend in boiling point as the chain increases and why?

A

As chain increases, boiling point increases:
- each CH2 added means 8 more electrons,
- therefore stronger London forces
- stronger forces require more energy to break so therefore higher temperature

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13
Q

What are Lewis structures useful for?

A

Visualising valence electrons

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14
Q

What are empirical formulas?

A

Simplest ratio of atoms in a molecule

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15
Q

What are molecular formulas?

A

Actual number of atoms present in molecule

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16
Q

What are the three different types of structural formula and how are they displayed?

A
  • Full structural formula: 2D representations showing all atoms and bonds and their positions
  • Condensed structural formula: All atoms and relative positions, without showing bonds
  • Skeletal structure: Carbon and Hydrogen atoms are not shown, end of each line and vertex represents C atom, functional groups shown
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17
Q

What are the 4 steps to naming a compound in Organic Chemistry?

A
  • identify the longest chain and thus the root name
  • identify the type of bonding in chain or ring
  • identify functional or alkyl groups (this may by at beginning or end of name)
  • use numbers to give position of groups or bonds along chain. Always aim to have lowest numbers.
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18
Q

What are the root names for 1-8 carbons?

A
  • 1: meth-
  • 2: eth-
  • 3: prop-
  • 4: but-
  • 5: pent-
  • 6: hex-
  • 7: hept-
  • 8: oct-
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19
Q

What follows the root name if:
- all bonds are single bonds
- one double bond
- one triple bond

A
  • single bonds: -an-
  • double bond: -en-
  • triple bond: -yn-
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20
Q

How would you end the name of a compound containing an alkane group (only hydrogen joined to chain)?

A

-e

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21
Q

How would you end the name of a compound containing a hydroxyl group?

A

-ol

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22
Q

How would you start the name of a compound containing an amine group?

A

amino-

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23
Q

How would you end the name of a compound containing an amide group?

A

-amide

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24
Q

How would you end the name of a compound containing a nitrile group?

A

-nitrile

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25
Q

How would you start the name of a compound containing a halo group?

A

chloro-, bromo- or iodo-

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26
Q

How would you end the name of a compound containing an aldehyde group?

A

-al

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27
Q

How would you end the name of a compound containing a ketone group?

A

-one

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28
Q

How would you end the name of a compound containing a carboxyl group?

A

-oic acid

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29
Q

What goes in the middle of a compound containing an ether group?

A

-oxy-

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30
Q

How would you end the name of a compound containing an ester group?

A

-oate

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31
Q

What is a structural isomer?

A
  • compounds with same chemical formula but a different structural formula
  • have unique physical and chemical properties
32
Q

What is a saturated hydrocarbon?

A

All bonds are single bonds (saturated with hydrogen)

33
Q

What is an unsaturated hydrocarbon?

A

Contains double or triple bond

34
Q

How do you number functional groups within a compound?

A

It is identified by the number of the carbon atom that its attached to

35
Q

When numbering, what takes priority, functional groups or substituents and c-c multiple bonds?

A

Functional groups take priority over substituents and c-c multiple bonds

36
Q

What determines if a compound is primary (1°)?

A

Carbon atom bonded to the functional group is also bonded to ONE other carbon atom

37
Q

What determines if a compound is secondary (2°)?

A

Carbon atom bonded to the functional group is also bonded to TWO other carbon atoms

38
Q

What determines if a compound is tertiary (3°)?

A

Carbon atom bonded to the functional group is also bonded to THREE other carbon atoms

39
Q

What determines the class of an alcohol?

A

The position of the hydroxyl group

40
Q

How do you classify an amine?

A
  • classified depending on number of alkyl groups (CnH2n+1) bonded to the nitrogen atom of functional group
41
Q

What is an aromatic hydrocarbon?

A

Aromatic hydrocarbons are characterized by the presence of benzene

42
Q

What is benzene?

A

Benzene is C6H6 composed of alternating double and single bonds

43
Q

What was Kekulé’s structure for benzene?

A
  • a hexagon with three double bonds
  • therefore equivalent to 3 ethene molecules
44
Q

What were the problems with Kekulé’s structure for benzene?

A
  • has 3 double bonds so should have similar reactivity to ethene but not the case as ethene undergoes addition reactions, benzene rarely does (as harsh condition required), instead undergoes substitution reactions
  • 3 double bonds also suggests that benzene had shorter double and longer single bonds but all bond lengths in benzene were exactly the same
  • benzene is more stable than Kekulé’s structure suggests, less energy required to hydrogenate a benzene molecule compared to 3 ethene molecules, therefore, bonds broken in benzene are stronger than the double bonds in ethene
45
Q

What is an arene?

A

A compound with one or more rings with pi electrons that are delocalised throughout the ring(s)

46
Q

When are compounds said to be aromatic?

A

When they contain an arene (like benzene)

47
Q

Describe the shape of benzene.

A
  • planar regular hexagon with bond angles of 120º
  • all bonds identical due to delocalization of electrons
  • each sp2 hybridised carbon atom in benzene forms: a σ bond with two other carbons and a σ bond with one hydrogen atom
  • the remaining p orbital is overlapping with the p orbitals on both sides of it so to achieve maximum overlap, the benzene ring must be planar
  • this results in the formation of a system of π bonds spread out over the whole ring, therefore the electrons are not bound to specific atoms but can instead freely move around the structure and are said to be delocalised
48
Q

What types of reactions can alkanes undergo?

A

Combustion
- complete with excess oxygen
- incomplete with limited oxygen (produces C and/or CO)
Halogenation
- free radical substitution (to form unsaturated alkenes/alkynes)
- elimination (to form unsaturated alkenes/alkynes)

49
Q

Describe the three stages of free radical substitution.

A
  • Initiation: The homolytic fission of the chlorine molecule in the presence of UV light.
  • Propagation: The radicals react with neutral atoms in attempt to gain stability. The target neutral atom then becomes a radical in the process.
  • Termination: Radicals join together creating new compounds in the process. This occurs either when:
  • emission of UV light is stopped preventing creation of radicals
  • concentration of hydrocarbons decrease because they “mop up” the radicals
50
Q

What is homolytic fission?

A

The two electrons of a covalent bond are split evenly between two atoms resulting in two free-radicals that each have a single electron

51
Q

What is heterolytic fission?

A

The bond creates a cation and an anion because the electrons are unevenly split (both electrons go to one atom)

52
Q

What is the species formed from when a molecule undergoes homolytic fission called?

A

Free-radical

53
Q

What is the condition required for free-radical substitution?

A

Occurs in presence of UV light

54
Q

What are the three types of reactions alkenes can undergo?

A
  • hydrogenation
  • halogenation
  • polymerisation
55
Q

What types of reactions do alkenes undergo?

A

Addition reactions

56
Q

What is the test for alkenes and what are the results?

A
  • bromine water test
  • colour change: brown —> colourless
57
Q

What type of catalyst is needed for the bromine water test?

A

Nickel catalyst

58
Q

What does the electrophilic halogenation of symmetrical alkenes involve the addition of and what does this form?

A
  • elemental halogens (e.g. Cl2, Br2, I2)
  • forms dihalogenated alkane
59
Q

What does the addition of hydrogen halide (HX) to a symmetrical alkene form?

A

Single mono-halogenated alkane

60
Q

What is addition polymerisation?

A

The reaction of many small monomers that contain carbon-carbon double bond, linking together forming a polymer (and losing their double bond in the process)

61
Q

What are the three types of reactions alcohols can undergo?

A
  • complete combustion
  • oxidation
  • condensation
62
Q

What does the complete combustion of an alcohol release?

A

Water and carbon dioxide

63
Q

What is required for the oxidation of alcohols?

A

Acidified potassium dichromate (K2Cr2O7)

64
Q

What does a primary alcohol oxidise into and what can this product oxidise into?

A

primary alcohol —> aldehyde —> carboxylic acid

65
Q

What does a secondary alcohol oxide into?

A

secondary alcohol —> ketone

66
Q

Condensation is a reaction between an alcohol and a _________?

A

Carboxylic acid

67
Q

What is often the catalyst in a condesation of alcohol reaction?

A

Sulphuric acid (H2SO4)

68
Q

What are the products formed from a condensation of alcohol reaction?

A

Ester and water

69
Q

True or false, esterification is a reversible process?

A

True

70
Q

Explain how nucleophilic substitution reactions work.

A
  • Halogenoalkanes contain a polar carbon – halogen bond (C-X)
  • This electron deficient carbon is open to attack by electron rich species known as nucleophiles
  • Nucleophiles contain a lone pair of electrons and sometimes have a full negative charge
71
Q

When is electrophilic substitution used?

A

Used for aromatic or compounds with double/triple bonds

72
Q

Benzene doesn’t readily undergo addition reactions, instead it undergoes __________________________?

A

Electrophilic substitution reactions

73
Q

What is an electrophile?

A

An electron poor species capable of accepting an electron pair

74
Q

What do the arrows show in an electrophilic substitution reaction?

A

The movement of electrons

75
Q

How do you turn acidified potassium dichromate(VI) solution green?

A

Oxidise a primary or secondary alcohol in the presence of potassium dichromate(VI)

IB Chemistry SL (12 decks)

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