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iB Chemistry > Topic 10 : Organic Chemistry > Flashcards

Topic 10 : Organic Chemistry Flashcards

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1
Q

Organic Chemistry

A
  1. Organic chemistry is the chemistry of carbon compounds
  2. Carbon forms a vast number of compounds because it can form strong covalent bonds with itself
  3. This enables it to form long chains of carbon atoms, and hence an almost infinite variety of carbon compounds are known
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2
Q

catenation

A

tendency of identical atoms to form covalent bonds with each other and hence form chains

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3
Q

Functional groups

A
  1. A functional group is a specific atom or group of atoms which confer certain physical and chemical properties onto the molecule
  2. Organic molecules are classified by the dominant functional group on the molecule
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4
Q

homologous series

A
  1. Organic compounds with the same functional group, but a different number of carbon atoms, are said to belong to the same homologous series
  2. As a homologous series is ascended, the size of the molecule increases
    This has an effect on the physical properties, such as boiling point and density

Assumptions about homologous series

  • each member has the same functional group
  • each member has the same general formula
  • each member has similar chemical properties
  • members have gradually changing physical properties, for example, boiling point, melting point and density
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5
Q

Boiling point across homologous series (alkane)

A
  1. The broad trend is that boiling point increases with increased molecular size
  2. Each additional -CH2 adds 8 more electrons to the molecule
  3. This increases the strength of the London Dispersion Forces
  4. Stronger LDF leads to a higher boiling point
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6
Q

Ways that organic compounds can be represented

A
  1. Empirical Formulae
  2. Molecular Formulae
  3. Structural Formulae
  4. Condensed Structural Formulae
  5. Displayed Formulae
  6. Skeletal Formulae
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7
Q

Empirical formula

A
  1. The empirical formula shows the simplest possible ratio of the atoms in a molecule
  2. For example: Hydrogen peroxide is H2O2 but the empirical formula is HO
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8
Q

Molecular formula

A
  1. The molecular formula shows the actual number of atoms in a molecule
  2. e.g. C4H10
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9
Q

Displayed Formula

A
  1. The displayed formula shows the spatial arrangement of all the atoms and bonds in a molecule
  2. It shows all of the atoms and the bonds present in an organic compound
  3. The bonds are represented as lines
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10
Q

Structural formula

A
  1. Similar to displayed formula but not all bonds are shown
  2. All atoms are still indicated using subscripts but carbon hydrogen bonds are often simplified
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11
Q

Condensed formula

A
  1. In a condensed structural formulae enough information is shown to make the structure clear, but most of the actual covalent bonds are omitted
  2. Only important bonds are always shown, such as double and triple bonds
  3. Identical groups can be bracketed together
  4. Side groups are also shown using brackets
  5. e.g. CH3CH2CH2CH3
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12
Q

Skeletal formula

A
  1. In a skeletal formula, most hydrogens are omitted and lines represent carbon atoms
  2. Functional groups are still shown and any other atom that isn’t carbon or hydrogen
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13
Q

Structural isomers

A
  1. Structural isomers are compounds that have the same molecular formula but different structural formulae
  2. Eg. propene and cyclopropane (are both C3H6 but look very different)
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14
Q

Different types of structural isomers

A
  1. Branch-Chain isomerism
  2. Positional isomerism
  3. Functional group isomerism
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15
Q

Branch-Chain isomerism

A
  1. Branch-Chain isomerism is when compounds have the same molecular formula, but their longest hydrocarbon chain is not the same
  2. This is caused by branching
  3. Eg. pentane and 2,2-dimethylpropane : Both compounds are made up of the same atoms (C5H12) however the longest carbon chain in pentane is 5 and in 2,2-dimethylpropane it is 3 (with two methyl branches)
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16
Q

Positional isomerism

A
  1. Positional isomers arise from differences in the position of a functional group in each isomer
  2. The functional group can be located on different carbons
  3. For example, butan-1-ol and butan-2-ol : Both compounds have an alcohol group and are made up of 4 carbon, 10 hydrogen and one oxygen atom however in butan-1-ol the functional group is located on the first carbon and in butan-2-ol on the second carbon
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17
Q

Functional group isomerism

A
  1. When different functional groups result in the same molecular formula, functional group isomers arise
  2. The isomers have very different chemical properties as they have different functional groups
  3. For example, butanol and ethoxyethane : Both compounds have the same molecular formula however butan-1-ol contains an alcohol functional group and ethoxyethane an ether functional group
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18
Q

Saturated hydrocarbons

A
  1. Saturated hydrocarbons are hydrocarbons which contain single bonds only resulting in the maximum number of hydrogen atoms in the molecule
  2. e.g. alkanes
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19
Q

Unsaturated hydrocarbons

A
  1. Unsaturated hydrocarbons are hydrocarbons which contain carbon-carbon double or triple bonds
  2. e.g. alkenes or alkynes
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20
Q

Side chains

A
  1. The hydrocarbon side-chain is shown in brackets in the structural formula
  2. The side-chain is named by adding ‘-yl’ to the normal alkane stem
  3. This type of group is called an alkyl group
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21
Q

Hydrocarbons

A
  1. Hydrocarbons are compounds containing hydrogen and carbon only
  2. There are four families of hydrocarbons: alkanes, alkenes, alkynes and arenes
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22
Q

Alkanes

A
  1. Alkanes have the general molecular formula CnH2n+2.
  2. They contain only single bonds
  3. saturated
  4. The suffix is -ane
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23
Q

Alkane uses

A
  1. Alkanes are quite unreactive but can burn well. This makes them useful fuels.
  2. They are unreactive due to their strong C-H bonds and C-C covalent bonds which are hard to break apart
  3. They also have a lack of polarity as electronegativities of the carbon and hydrogen atoms in alkanes are almost the same so they share electrons fairly equally - thus they do not react with polar reagents
  4. ONLY REACT IN COMBUSTION AND SUBSTITUTION BY HALOGEN
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24
Q

Alkenes

A
  1. Alkenes have the general molecular formula CnH2n
  2. They are said to be unsaturated
  3. Alkenes are named with the suffix -ene
  4. In molecules with a straight chain of 4 or more carbon atoms, the position of the C=C double bond must be specified
  5. The carbon atoms on the straight chain must be numbered, starting with the end closest to the double bond
  6. The lowest-numbered carbon atom participating in the double bond is indicated just before the -ene:
  7. More reactive than alkanes
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25
Q

Alkynes

A
  1. Alkynes have the general molecular formula CnH2n-2
  2. The triple bond makes them unsaturated molecules
  3. Alkynes are named with the suffix -yne
  4. As with alkenes, in molecules with a straight chain of 4 or more carbon atoms, the position of the triple bond must be specified
  5. The carbon atoms on the straight chain must be numbered, starting with the end closest to the triple bond
  6. The lowest-numbered carbon atom participating in the triple bond is indicated just before the -yne:
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26
Q

Halogenoalkanes

A
  1. Halogenoalkanes have the general molecular formula, CnH2n+1X, where X represents a halogen
  2. Haloalkanes are named using the prefix chloro-, bromo- or iodo-, with the ending -ane
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27
Q

Alcohols

A
  1. Alcohols are a family of molecules that contain the hydroxyl functional group, -OH
  2. Their general formula is CnH2n+1OH
  3. If there are two -OH groups present the molecule is called a diol
  4. Alcohols are classified as primary, secondary or tertiary depending on the number of carbons attached to the functional group carbon
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28
Q

Ethers

A
  1. Ethers are a family of molecules that contain the ether functional group, R-O-R, where R is an alkyl group
  2. Their general formula is CnH2n+2O
  3. The nomenclature of ether follows the pattern alkoxy + alkane
  4. The longest carbon chain is assigned the alkane and the shortest carbon chain is assigned the alkyoxy group
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29
Q

Carbonyls

A
  1. Carbonyl is the collective name for compounds containing the functional group C=O
  2. The general formula of a carbonyl is CnH2nO
  3. The two sub-families of carbonyls are aldehyde and ketone
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30
Q

Aldehydes

A
  1. If the carbonyl group is on the end of a chain then it is an aldehyde and has the functional group formula, RCHO the H is written before the O so as not to confuse it with an alcohol
  2. The nomenclature of carbonyls follows the pattern alkan + al
  3. There is no need to use numbers in the name as aldehyde will always be on the number 1 carbon atom
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31
Q

Ketones

A
  1. Ketones have a minimum of three carbons and have the general functional group formula, RCOR
  2. The nomenclature of ketones follows the pattern alkan + one
  3. After butanone, the carbonyl group can have positional isomers, so numbering must be used
  4. For example pentan-2-one and pentan-3-one
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32
Q

Aldehydes and Ketones

A
  1. As they have a very similar functional group arrangement, aldehydes and ketones show similar chemical reactions
  2. Differences in their chemistry are due to the reactions that involve the H on the aldehyde or the nature of the R group
  3. The difference in electronegativity between oxygen and carbon means the C=O is polar, leading to dipole-dipole attractions between the molecules which results in:
    - higher than expected boiling points for small molecules
    - solubility in water for the lower members of the families
  4. Aldehydes and ketones with the same number of carbons are functional group isomers
33
Q

Carboxylic acids

A
  1. Carboxylic acids is the name given to compounds containing the functional group carboxyl, -COOH
  2. The general formula of a carboxylic acid is CnH2n+1COOH which can be shortened to just RCOOH
  3. The nomenclature of carboxylic acid follows the pattern alkan + oic acid
  4. There is no need to use numbers in the name as the carboxyl group will always be on the number 1 carbon atom
34
Q

Esters

A
  1. Esters are functional group isomers of carboxylic acids and contain the functional group, carboxylate, -COOR
  2. The general formula of an ester is usually represented as RCOOR where R can be the same or different on either side of the carboxylate group
  3. The nomenclature of esters follows the pattern alkyl + alkanoate
  4. The alkyl group in the name is the R group attached to the oxygen
35
Q

Carboxylic acids and esters

A
  1. Carboxylic acids and esters contain few similarities in their chemical and physical properties
  2. H-bonds are present between carboxylic acid molecules and not between esters, so this affects the melting point, boiling point and solubility:
  3. Smaller chain carboxylic acids are soluble in water and have higher boiling points than expected (e.g. ethanoic acid is 117C)
  4. Esters are insoluble in water and have lower boiling points than their isomeric carboxylic acids ( e.g. methyl methanoate is 31C)
36
Q

Organic Nitrogen Compounds

A
  1. Amines
  2. Amides
  3. Nitriles
37
Q

Amines

A
  1. Amine is the name given to compounds containing the functional group amino, -NH2
  2. Amines are derived from ammonia where one H in ammonia (NH3)has been replaced by an R (alkyl) group
  3. The general formula of an amine is CnH2n+1NH2 which can be shortened to just RNH2
38
Q

Amides

A
  1. Amide is the name given to compounds containing the functional group carboxamide, -CONH2
  2. Amides are a combination of amino and carbonyl groups
  3. The general formula of an amide is CnH2n+1CONH2 which can be shortened to just RCONH2
39
Q

Nitriles

A
  1. Nitriles are compounds containing the functional group nitrile, -CN
  2. This is the same CN group that is called a cyanide group as an ion, just as hydroxyl group, OH is called hydroxide in inorganic chemistry
  3. The general formula of an nitrile is CnH2n+1CN which can be shortened to just RCN
40
Q

Primary atoms

A
  1. Primary alcohols and halogenoalkanes are those in which the carbon atom bonded to the functional group is attached to one other carbon atom (or alkyl group)
41
Q

Secondary atoms

A
  1. In secondary alcohols and halogenoalkanes the functional group carbon atom is attached to two other carbon atoms (or alkyl groups)
42
Q

Tertiary atoms

A
  1. In tertiary alcohols and halogenoalkanes the functional group carbon atom is attached to three other carbon atoms (or alkyl groups)
43
Q

Benzene

A
  1. Benzene is a planar regular hexagon with bond angles of 120º
  2. The overlap of p orbitals of the double bond forms a ring of delocalised electrons which spreads the electron density and stabilises it
  3. Therefore it does not actually have alternating double bonds but rather all the bonds have a length of 1.5
  4. Thus is can not undergo electrophilic addition but rather undergoes electrophilic substitution
44
Q

Combustion of alkanes

A
  1. Alkanes are combusted (burnt) on a large scale for their use as fuels
  2. They also react in free-radical substitution reactions to form more reactive halogenoalkanes
45
Q

Complete combustion of alkanes

A
  1. When alkanes are burnt in excess (plenty of) oxygen, complete combustion will take place and all carbon and hydrogen will be oxidised to carbon dioxide and water respectively
  2. For example, the complete combustion of octane to carbon dioxide and water
46
Q

Incomplete combustion of alkanes

A
  1. When alkanes are burnt in only a limited supply of oxygen, incomplete combustion will take place and not all the carbon is fully oxidised
  2. Some carbon is only partially oxidised to form carbon monoxide
  3. For example, the incomplete combustion of octane to form carbon monoxide (which is toxic and binds to haemoglobin making it hard for oxygen to travel around the body)
47
Q

Halogenation of Alkanes

A
  1. aka free-radical substitution of alkanes
  2. Alkanes can undergo free-radical substitution in which a hydrogen atom gets substituted by a halogen (chlorine/bromine)
  3. Since alkanes are very unreactive, ultraviolet light (sunlight) is needed for this substitution reaction to occur
48
Q

Steps of free-radical substituion

A
  1. Initiation steps: the halogen bond (Cl-Cl or Br-Br) is broken by UV energy to form two radicals
  2. Propagation steps: These radicals create further radicals in a chain type reaction called the propagation step (the radical is regenerated)
  3. The reaction is terminated when two radicals collide with each other in a termination step
49
Q

Propagation steps of free-radical substitution (alkanes)

A
  1. Free radicals are very reactive and will attack the unreactive alkanes
  2. A C-H bond breaks (each atom gets an electron from the covalent bond)
  3. An alkyl free radical is produced
  4. This can attack another chlorine/bromine molecule to form the halogenoalkane and regenerate the chlorine/bromine free radical
  5. This free radical can then repeat the cycle
50
Q

Reactivity of alkenes

A
  1. Alkenes are hydrocarbons containing a carbon-carbon double bond
  2. The atoms around the carbon-carbon double bond adopt a planar arrangement and the bond angle is 120o
  3. Alkenes can undergo addition reactions (the double bond opens up)
  4. Addition is the combination of two or more molecules to form a single molecule. Addition reactions are generally faster than substitution reactions
  5. The ability of alkenes to undergo addition means that they are much more reactive than alkanes
51
Q

Hydrogenation of Alkenes

A
  1. Alkenes are very useful compounds as they can undergo many types of reactions
  2. They can therefore be used as starting molecules when making new compounds
  3. The reaction between an alkene and hydrogen is known as hydrogenation or reduction
  4. It requires a nickel catalyst, temperature of 200 °C and a pressure of 1000 kPa
52
Q

Halogenation of Alkenes

A
  1. The reaction between alkenes and halogens is known as halogenation
  2. It is an example of an electrophilic addition where an electrophile (‘electron seeker’) joins onto to a double bond
  3. The C=C double bond is broken, and a new single bond is formed from each of the two carbon atoms
  4. The reaction occurs readily at room temperature and is the basis for the test for unsaturation in molecules
53
Q

Testing for saturation

A
  1. Halogens can be used to test if a molecule is unsaturated (i.e. contain a double bond)
  2. Br2 is an orange or yellow solution, called bromine water
  3. The unknown compound is shaken with the bromine water
  4. If the compound is unsaturated, an addition reaction will take place and the coloured solution will decolourise
54
Q

Hydrohalogenation of Alkenes

A
  1. Alkenes will react readily with hydrogen halides such as HCl and HBr to produce halogenoalkanes
  2. This reaction is known as hydrohalogenation
  3. It is also an electrophilic addition reaction that occurs quickly at room temperature
  4. All the hydrogen halides react in this way, but the fastest reaction occurs in the order HI > HBr > HCl due to the increasing bond strength of the hydrogen-halogen bond, so the weakest bond reacts most easily
55
Q

Hydration of Alkenes

A
  1. When alkenes are treated with steam at 300C, a pressure of 60 atmospheres and sulfuric acid (H2SO4) or phosphoric acid (H3PO4) catalyst, the water is added across the double bond in a reaction known as hydration
  2. An alkene is converted into an alcohol
  3. Alkene + steam –> Alcohol
56
Q

Addition polymerisation

A
  1. Addition polymerisation is one of the most important addition reactions of alkenes which form the basis of the plastic industry
  2. Addition polymerisation is the reaction in which many monomers containing at least one C=C double bond form long chains of polymers as the only product
  3. Just like any other addition reaction of alkenes, addition polymerisation gives only one product
57
Q

Polymer

A

A polymer is a long-chain molecule that is made up of many repeating units

58
Q

monomer

A

The small, reactive molecules that react together to form the polymer are called monomers

59
Q

repeat unit

A
  1. A repeat unit is the smallest group of atoms that when connected one after the other make up the polymer chain
  2. poly(alkenes) - alkene is the repeating unit
60
Q

Combustion of Alcohols

A
  1. Alcohols react with oxygen in the air when ignited and undergo complete combustion to form carbon dioxide and water
  2. Lower alcohols burn with an almost invisible flame and make good fuels
  3. e.g. Alcohol + oxygen → carbon dioxide + water
61
Q

Oxidation of Primary Alcohols

A
  1. Primary alcohols can be oxidised to form aldehydes which can undergo further oxidation to form carboxylic acids
  2. The oxidising agents of alcohols include acidified K2Cr2O7 (Potassium dichromate) or acidified KMnO4 (Potassium permanganate)
62
Q

Acidified potassium dichromate(VI)

A
  1. Acidified potassium dichromate(VI), K2Cr2O7, is an orange oxidising agent
  2. Acidified means that that the potassium dichromate(VI) is in a solution of dilute acid (such as dilute sulfuric acid)
  3. For potassium dichromate(VI) to act as an oxidising agent, it itself needs to be reduced
  4. When alcohols are oxidised the orange dichromate ions (Cr2O72-) are reduced to green Cr3+ ions
63
Q

Acidified potassium manganate(VII)

A
  1. Acidified potassium manganate(VII), KMnO4, is a purple oxidising agent
  2. As with acidified KMnO4 the potassium manganate(VII) is in an acidic medium to allow reduction of potassium manganate(VII) to take place
  3. When alcohols are oxidised, the purple manganate ions (MnO4-) are reduced to colourless Mn2+ ions
64
Q

Further oxidation of primary alcohols

A
  1. If the aldehyde is not distilled off, further oxidation with excess oxidising agent will oxidise it to a carboxylic acid
  2. The reaction takes some time to complete and requires sustained heating
65
Q

Test for alcohols

A
  1. The oxidation using acidified dichromate provides the basis for the test for alcohols as the reaction gives a strong colour change from orange to green
  2. Unfortunately, it does not work for tertiary alcohols, which cannot be oxidised
66
Q

Oxidation of secondary alcohols

A
  1. Secondary alcohols can be oxidised to form ketones only
67
Q

Oxidation of tertiary alcohols

A
  1. Tertiary alcohols do not undergo oxidation
  2. This is because there must be a hydrogen on the functional group carbon, which breaks off to form water
  3. There are only C-C bonds on the functional group carbon in a tertiary alcohol
68
Q

Fractional Distillation (oxidation of alcohols)

A
  1. To produce an aldehyde from a primary alcohol the reaction mixture must be heated
  2. The aldehyde product has a lower boiling point than the alcohol ( since it has lost the H-bonding) so it can be distilled off as soon as it forms
  3. Distillation can be carried out using a simple side arm arrangement which acts as an air condenser or the vapours can be made to pass through a condenser
69
Q

Heating under reflux

A
  1. For reactions that require sustained heating the apparatus has to be modified
  2. To prevent loss of volatile reactants the apparatus includes a condenser in the vertical position which returns components back into the reaction flask
  3. This is known as heating under reflux (reflux means re-boiling)
70
Q

Esterfication of alcohols

A
  1. Esters are compounds with an -COOR functional group and are characterised by their sweet and fruity smells
  2. They are prepared from the condensation reaction between a carboxylic acid and alcohol with concentrated H2SO4 (sulfuric acid) as catalyst
  3. This is also called esterification
71
Q

Reactions of Halogenoalkanes

A
  1. Halogenoalkanes are much more reactive than alkanes due to the presence of the electronegative halogens
  2. The halogen-carbon bond is polar causing the carbon to carry a partial positive and the halogen a partial negative charge
  3. A nucleophilic substitution reaction is one in which a nucleophile attacks a carbon atom which carries a partial positive charge
  4. An atom that has a partial negative charge is replaced by the nucleophile
72
Q

Halogenoalkane to form an alcohol

A
  1. The reaction of a halogenoalkane with aqueous alkali results in the formation of an alcohol
  2. The halogen is replaced by the OH-
  3. The aqueous hydroxide (OH- ion) behaves as a nucleophile by donating a pair of electrons to the carbon atom bonded to the halogen
  4. Hence, this reaction is a nucleophilic substitution
  5. The reaction is slow at room temperature so to ensure a high yield it is heated under reflux
  6. Since haloalkanes are not usually soluble in water, a polar solvent such as ethanol is often used as it will dissolve haloalkanes as well as sodium hydroxide
73
Q

Arene

A
  1. Arene is the collective name given to compounds with one or more rings that are delocalised throughout the ring(s)
  2. e.g. benzene
  3. Compounds with this feature are said to be aromatic
  4. This doesn’t mean they are necessarily smelly, although a lot of naturally occurring arenes do have distinctive smells!
  5. The functional group in benzene is known as a phenyl group when attached to other molecules
74
Q

CFCs

A
  1. Chlorofluorocarbons (CFCs)

2. nontoxic, nonflammable chemicals containing atoms of carbon, chlorine, and fluorine.

75
Q

Ozone

A
  1. Allotrope of oxygen gas
  2. Made naturally in the atmosphere
  3. It is also made by photocopiers and laser printers
76
Q

Ozone formation

A
  1. Oxygen gas molecules are bombarded by high energy UV light from the sun
  2. This causes them to break and form oxygen radicals
  3. The oxygen radicals react with more oxygen gas molecules making ozone (O3)
77
Q

Ozone destruction

A
  1. The ozone gas molecules are hit by other UV radiation from the sun
  2. They break up to form oxygen gas molecules and oxygen radicals
  3. Oxygen radicals join up to form O2 molecules (termination step)
78
Q

How do CFCs remove ozone

A
  1. The stable CFCs last long enough in the atmosphere to reach the stratosphere. Very reactive chlorine radicals are formed under UV
  2. The chlorine radicals react with ozone molecules in the stratosphere
  3. They remove them from the ozone cycle
  4. The ozone goes back to being oxygen gas.
  5. The ClO. radical takes oxygen radicals out of the ozone cycle.

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