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AQA A-Level Organic Chemistry > [3.3.1] Introduction to Organic Chemistry > Flashcards

[3.3.1] Introduction to Organic Chemistry Flashcards

Nomenclature, Reaction Mechanisms & Isomerism.

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1
Q

What is a hydrocarbon?

A

A compound consisting of hydrogen and carbon only.

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2
Q

What does saturated mean?

A

Contain single carbon-carbon bonds only.

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3
Q

What does unsaturated mean?

A

Contains a C=C double bond.

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4
Q

What is the molecular formula?

A

Shows the actual number of each type of atom.

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5
Q

What is the empirical formula?

A

Shows the simplest whole number ratio of atoms of each element in a compound.

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6
Q

What is the general formula?

A

Algebraic formula for a homologous series e.g. for alkenes CnH2n.

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7
Q

What is the structural formula?

A

Shows the minimal detail that shows the arrangement of atoms in a molecule e.g. for butane = CH₃CH₂CH₂CH₃.

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8
Q

What is the displayed formula?

A

Shows all the covalent bonds and atoms present in a molecule.

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9
Q

What is the skeletal formula?

A

Shows the simplified organic formula, shown by removing hydrogen atoms from alkyl chains, leaving just a carbon skeleton and associated functional groups.

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10
Q

Draw the skeletal formula for butan-1-ol.

A
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11
Q

What is a functional group?

A

An atom or group of atoms which when present in different molecules causes them to have similar chemical properties.

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12
Q

What is a homologous series? What are the characteristics of one?

A
  • Homologous series are families of organic compounds with the same functional group and same general formula.

CHARACTERISTICS

  • They show a gradual change in physical properties.
    • e.g. boiling point.
  • Each member differs by CH₂ from the last.
  • Same chemical properties.
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13
Q

Give some examples of homologous series.

A
  • Alkane.
  • Alkenes.
  • Alcohols.
  • Halogenoalkanes.
  • Aldehydes.
  • Ketones.
  • Carboxylic acids.
  • Esters.
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14
Q

What are the general rules for naming carbon chains?

A
  1. Count the longest chain and name appropriately.
    • Meth = 1 carbon atom.
    • Eth = 2 carbon atoms.
    • Prop = 3 carbon atoms.
    • But = 4 carbon atoms.
    • Pent = 5 carbon atoms.
    • Hex = 6 carbon atoms.
    • Hept = 7 carbon atoms.
    • Oct = 8 carbon atoms.
    • Non = 9 carbon atoms.
    • Dec = 10 carbon atoms
  2. Find any branched chains and count how many carbons they contain.
  3. Add the appropriate prefix for each branched chain.
    • e.g. CH₃ = methyl, C₂H₅ = ethyl, C₃H₇ = propyl…
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15
Q

What are the general rules for naming functional groups?

A
  1. Functional group is named by a prefix or suffix.
    • If the suffix starts with a vowel, remove the -e from the stem alkane name.
      • e.g. Propan-1-ol, butan-1-amine, ethanoic acid, ethanoylchloride, butanamide.
    • If the suffix starts with a consonant or there are two or more of a functional group meaning di or tri needs to be used then do not remove the -e from the stem alkane name.
      • e.g. Propanenitrile, ethane-1,2-diol, proanedioic acid, propane1,2,3-triol, pentane-2,4-dione.
  2. The position of the functional group on the carbon chain is given by a number counting from the end of the molecule that gives the functional group the lowest number.
    • For aldehydes, carboxylic acids & nitriles, the functional group is always on carbon 1.
  3. We only include numbers if they are needed to avoid ambiguity.
  4. The functional groups take precedence over branched chains in giving the lowest number.
  5. Where there are two or more of the same groups, di-, tri-, tetra-, penta- and hexa- are used.
  6. Words are separated by numbers with dashes, numbers are separated by commas and if there is more than one functional group or side chain, the groups are listed in alphabetical order (ignoring any di, tri etc.).
  7. When compounds contain more than one functional group, the order of precedence determines which groups are named with prefix or suffix forms.
    • The highest precedence takes the suffix (and the lowest number on the carbon chain), with all others taking the prefix form.
    • Order of priority highest first: carboxylic acids > aldehydes > ketones > alcohols > alkenes > halogenoalkanes.
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16
Q

How do you name alkanes?

A
  • Using the suffix -ane.
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17
Q

Write the structural formula and draw the skeletal formula of butane.

A
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18
Q

Draw the skeletal formula for 2-methylbutane.

A
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19
Q

Draw the skeletal formula for cyclohexane.

A
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20
Q

Name this molecule.

A

Methylpropane.

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21
Q

How do you name alkenes?

A
  1. A double bond will be between two carbon atoms. Use the lower number of the two to show the position of the double bond.
    • e.g. But-2-ene.
  2. The name for alkenes may include E or Z at the start to show the type of stereoisomer.
    • e.g. Z-but-2-ene.
  3. If more than one double bond is present, then suffix ends in diene or triene.
    • The stem ends in a.
      e.g. penta-1,3-diene.
  4. The suffix -en for alkenes can go in front of other suffixes.
    • e.g. 2-bromobut-3-en-1-ol and E-but-2-enoic acid.
      • The alcohol and carboxylic acid groups have higher priority than the alkene group so take precedence with numbering.
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22
Q

Draw the skeletal formula for but-2-ene.

A
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23
Q

Draw the skeletal formula for cyclohexene.

A
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24
Q

Draw the skeletal formulae of Z-but-2-ene, penta-1,3-diene and E-but-2-enoic acid.

A
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25
Q

Write the structural formula of 2-bromobut-3-en-1ol

A
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26
Q

Write the structural formula and draw the skeletal formula of propene.

A
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27
Q

How do you name halogenoalkanes?

A
  • Class the halogen as a substituent on the carbon chain and use the prefixes -fluoro, -chloro, -bromo or -iodo.
    • Give the position number if necessary.
    • Multiple functional groups and side chains are listed in alphabetical order ignoring any di, tri etc.)
      • e.g. 2,3-dicholoro-1-fluoro-3-methylpentane.
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28
Q

Draw the displayed formula of 2-bromobutane.

A
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29
Q

Draw the displayed and skeletal formula of 1-chloropropane.

A
30
Q

Draw the skeletal formula of 2,3-dichloro-1-fluoro-3-methylpentane.

A
31
Q

Draw the skeletal formula of 5,5-dibromo-4-iodo-3-methylpent-1-ene.

A
32
Q

Name this molecule.

A

2,3-dibromopentane.

33
Q

Name this molecule.

A

2,2-dichloro-1-fluorobutane.

34
Q

Name this molecule.

A

3-bromo-1-fluoropentane.

35
Q

How do you name alcohols?

A
  1. These have the ending -ol and if necessary the position number for the OH group is added between the name stem and the -ol.
    • e.g. butan-2-ol.
  2. If there are two or more -OH groups then di and tri are used.
    • Add the ‘e’ onto the stem name though.
      • e.g. ethane-1,2-diol & propane-1,2,3-diol.
  3. The OH group has a higher priority than the halogenoalkane group and alkene so takes precedence in numbering.
    • E-3,6-dichlorohex-4-en-1-ol, the OH is on carbon 1.
  4. If the compound has an -OH group in addition to another functional group with a higher priority, then the priority group gets the suffix ending and the OH can be named with the prefix hydroxy-.
36
Q

Draw the displayed and skeletal formulae for propan-1-ol.

A
37
Q

Draw the structural formula of butan-2-ol.

A
38
Q

Draw the structural formula of ethane-1,2-diol.

A
39
Q

Draw the structural formula of propane-1,2,3-diol.

A
40
Q

Draw the skeletal formula of E-3,6-dichlorohex-4-en-1-ol.

A
41
Q

Draw the structural formula of 2-hydroxypropanoic acid.

A
42
Q

How do you name aldehydes?

A
  1. An aldehyde’s name ends in -al.
    • e.g. ethanal.
  2. Aldehydes always have the C=O bond on the first carbon of the chain so it does not need an extra number.
  3. If two aldehyde groups then di is put before -al and an e is added to the stem.
    • e.g. pentanedial.
  4. Aldehydes have a higher priority than alcohol so the -OH group uses the hydroxy prefix.
    • e.g. 4-hydroxybutanal.
43
Q

Draw the displayed and skeletal formulae of ethanal.

A
44
Q

Draw the skeletal formula of pentanedial.

A
45
Q

Draw the skeletal formula of 4-hydroxybutanal.

A
46
Q

How do you name ketones?

A
  1. Ketones end in -one.
    • e.g. propanone.
  2. When ketones have 5 carbons or more, then it needs a number to the show the position of the double bond.
  3. If there are two ketone groups, di is put before -one and an e is added to the stem.
    • e.g. pentane-2,4-dione.
47
Q

Draw the displayed formulae of propanone and pentane-2,4-dione.

A
48
Q

How do you name carboxylic acids?

A
  1. These have the ending -oic acid but no number is necessary for the acid group as it must always be at the end of the chain.
    • e.g. propanoic acid
  2. Numbering always starts from the carboxylic acid end.
  3. If there are carboxylic acids on both ends of the chain then it is called a -dioic acid.
49
Q

Draw the displayed formula of propanoic acid and ethanedioic acid.

A
50
Q

Draw the skeletal formula of 5-hydroxy-4-methylpentanoic acid.

A
51
Q

What is homolytic fission? What are free radicals?

A
  • Each atom gets one electron from the covalent bond.
  • It forms two free radicals.
    • A free radical is a reactive species which possesses an unpaired electron.
    • Freed radicals do not have a charge and are represented by a ·.
52
Q

Show the process of homolytic fission on the molecule below.

A
53
Q

What is heterolytic fission?

A
  • Where one atom gets both electrons.
  • Heterolytic fission produces ions.
  • Most organic reactions occur via heterolytic fission.
54
Q

Show the process of heterolytic fission on the molecules below.

A
55
Q

What does a one-headed arrow represent?

A

Movement of one electron.

56
Q

What does a two-headed arrow represent?

A

Movement of a pair of electrons.

57
Q

How is the formation of a covalent bond represented?

A

The formation of a covalent bond is shown by a curly arrow that starts from the lone electron pair or from another covalent bond.

58
Q

How is the breaking of a covalent bond represented?

A

The breaking of a covalent bond is shown by a curly arrow starting from the centre of a bond.

59
Q

What is a structural isomer? What do they arise from?

A

Same molecular formula different structure (or structural formulae).

STRUCTURAL ISOMERISM CAN ARISE FROM:

  1. Chain isomerism.
  2. Position isomerism.
  3. Functional group isomerism.
60
Q

What is a chain isomer?

A

Compounds with the same molecular formula, but different structures of the carbon skeleton.

61
Q

What is a position isomer?

A

Compounds with the same molecular formula, but different structures due to different positions of the same functional group on the same carbon skeleton.

62
Q

What is a functional group isomer?

A

Compounds with the same molecular formula, but with atoms arranged to give different functional groups.

63
Q

What are stereoisomers?

A

Stereoisomers have the same structural formula, but have a different spatial arrangement of atoms.

64
Q

How do E-Z stereoisomers arise?

A

E-Z STEREOISOMERS ARISE WHEN…

  1. When there is a ristricted rotation around the C=C double bond.
  2. There are two different groups/atoms attached to both ends of the double bond.
65
Q

What type of functional group can exhibit E-Z stereoisomers?

A

Alkenes.

66
Q

What is a priority group?

A

The atom with the bigger atomic number is classed as the priority atom.

67
Q

How do you name E-Z stereoisomers?

A
  1. First determine the priority groups on both sides of the double bond.
  2. If the priority atom is on the same side of the double bond, it is labelled Z from the German zusammen.
    • The Zame Zide!
  3. If the priority atom is on the opposite side of the double bond, it is labelled *E** from the German entgegen.
    • The Epposite side!
68
Q

Does but-1-ene show E-Z stereoisomerism?

A
69
Q

Draw the displayed and skeletal formulae of the E-Z isomerism present in but-2-ene.

A
70
Q

Out of the two E-Z stereoisomers below, which has the highest boiling point?

A

Z-1,2-dichloroethene

  • Boiling point = 60°C
    1. This molecule is polar.
    2. The polar C-Cl bonds are on the same side of the molecule - one side of the molecule is slightly negative.
    3. The intermolecular forces are both van der Waals & permanent dipole-dipole attractions.

E-1,2-dichloroethene

  • Boiling point = 48°C
    1. The molecule is non-polar.
    2. The polar C-Cl bonds are on opposite sides of the molecule - the dipoles cancel out.
    3. The intermolecular forces are only van der walls so lower boiling point.

AQA A-Level Organic Chemistry (6 decks)

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