⚫️ Topic 6: Organic Chemistry Flashcards

1
Q

How many bonds can a carbon atom form?

A

4 covalent bonds

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2
Q

What is the order of carbons?

A
1 - meth-
2 - eth-
3 - prop-
4 - but-
(Pent-, hex-, hept-, oct-, non-, dec-, …)
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3
Q

What is a straight (or branched) chain of molecules called?

A

Aliphatic

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4
Q

What is a closed ring of molecules called?

A

Alicyclic

A cycloalkane will have the same general formula as an alkene

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5
Q

What does a saturated molecule mean?

A

Contains only C-C single bonds (contains as much hydrogen as possible)

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6
Q

What does an unsaturated molecule mean?

A

Has C=C double bonds (/triple) - (has room for more hydrogens)

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7
Q

What does a molecular formula mean?

A

Gives exact number of each atom present with all of the same atoms grouped together

Eg. C3H6O2 NOT C2H5COOH

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8
Q

What is a structural formula?

A

Written in groups of the bonds around each carbon atom (Displayed formula ‘displays’ it all out), but use skeletal formula most of the time (ends of lines = carbons)

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9
Q

What is a functional group?

A

An atom or group of atoms that gives the compound some distinctive and predictable (chemical) properties/ reactions

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10
Q

What is a homologous series and what are the features of it?

A

A family of chemicals with the same functional group which differ by CH2 from the next member

  • similar chemical properties (eg. All alkanes form carbon dioxide and water when burnt completely in air)
  • trends in physical properties (eg. Increase in boiling temp.)
  • next member differs by CH2
  • same general formula
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11
Q

What does nomenclature mean?

A

Naming organic compounds

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12
Q

What do you first look for when naming organic compounds?

A

The longest carbon chain - make sure to check every chain to find the longest (may not be horizontally)
(This goes at the end of the name)
This also contains the functional group (the lowest locant number should be used for functional group)

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13
Q

What is a locant number?

A

Shows positions of atoms or groups (methyl, ethyl, bromo, hydroxyl) - the numbers represent the carbon atoms in the longest chain that the atoms or groups are attached to (eg. 2-, 3-, 2,2-)
- the lowest locant numbers possible should be used
- remember di, tri if multiple of a group or atom
Then add this before the longest chain name, making sure in alphabetical order (eg. Ethyl before methyl)

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14
Q

If something is written with brackets (eg. CH3CH(CH3)CH(CH3)2) how would the displayed formula look?

A

The parts in brackets would be drawn coming off the sides of the central carbon chain (side chains) - remember carbon atoms need 4 bonds (4 lines coming off it)

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15
Q

What are the two types of isomers?

A
  • structural isomers

- stereoisomers

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16
Q

What is a structural isomer?

A

A molecule with the same molecular formula, but a different structural formula. There are three different types:

  • chain isomerism
  • position isomerism
  • functional group isomerism
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17
Q

What are the three different types of structural isomerism, and explain what they are, with properties?

A
  • chain isomerism - carbon chain is different (eg. Straight chain and branched chain) — similar chemical properties, slightly different physical properties (eg. The more branching, the lower the boiling point)
  • position isomerism - the functional groups are in different locations on the carbon chain, but same carbon skeleton + same functional group (eg. Propan-1-ol and propan-2-ol) — similar chemical + physical properties
  • functional group isomerism - different functional group, but same molecular formula — different chemical + physical properties
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18
Q

What is stereoisomerism?

A

Compounds with the same molecular formula and structural formula, but with atoms arranged differently in 3D. The two types are geometric isomerism and optical isomerism

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19
Q

What are geometric isomers and why does it only occur in certain molecules?

A

(There are only ever two geometric isomers) Compounds with a C=C double bond with atoms/groups attached to it at different positions (switch the atoms or groups that are attached to ONE C around)

C=C double bond has restricted rotation - ‘freezes’ groups on either side of the bond. Single bonds can rotate, so geometric isomerism does not occur in alkanes.

ALSO,
However it does not occur in all alkenes - BOTH C atoms of the C=C must have two different groups/atoms attached
(Present with C=C in the middle and the other two bonds coming out of the ‘corners’)

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20
Q

How do you name geometric isomers?

A
  • the group/ atom with the highest mass takes priority - look at atomic numbers of atoms directly bonded to each carbon - if the same, move to the next atom in the chain
    - if priority values are opposite side: E
    - if priority values are the same side: Z (zame zide)
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21
Q

When can you use cis/trans notation?

A

If the two priority groups in a molecule are the same
Z = cis
E = trans

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22
Q

What is crude oil and how is it involved with fractional distillation?

A
  • obtained by drilling into the ground
  • crude oil is a mixture of mostly alkanes of different chain lengths, and therefore different boiling points (which is what determines the fraction it will be in - short chain hydrocarbons have low boiling point so are at the top of the fractionating column [petrol, paraffin], long chain hydrocarbons have high boiling points so are at the bottom [bitumen]) (cool at top, hot at bottom)
  • crude oil is heated as it enters the column - vapours rise and condense at their boiling point
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23
Q

Why is fractional distillation necessary?

A

(Alkane fuels are obtained from the fractional distillation, cracking and reforming of crude oil)
As a mixture, crude oil isn’t very useful, but the different hydrocarbons that make up the mixture (fractions) are useful - each fraction has different applications (eg. Heating, cooking, road surfaces)

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24
Q

After the fractional distillation process, how are the products made even more useful?

A

Cracking - some excess heavier fractions (long chain alkanes) are broken down into smaller, more useful compounds which are in higher demand (eg. petrol)
- produces a smaller alkane and one or more alkene molecules (which can be used to make plastics)
Conditions: high temp. (to vaporise?) + catalyst (Al2O3)

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25
Q

How can you confirm that cracking has been successful?

A
  • use bromine water to test for presence of an alkene (yellow —> colourless) — (the C=C will break and the Br2 will add across the double bond)
  • smaller molecules should have been made - look for bubbles (gas being produced) which shows the product has a lower boiling temp.
26
Q

Why does the chamber used for cracking not contain oxygen?

A

To prevent combustion of the hydrocarbon to water and carbon dioxide

27
Q

What is reforming?

A

Converting straight chain hydrocarbons into branched and/or cyclic hydrocarbons for efficient combustion (straight chain molecules burn less efficiently than branched or cyclic hydrocarbons)
Conditions: heat + pressure
Products: a hydrocarbon with the same number of carbons, but cyclic or branched (may be less hydrogens) and hydrogen

28
Q

What are the products of combustion of alkane fuels?

A

Complete: (all atoms in fuel are fully oxidised)

  • water (all H atoms are completly oxidised to water)
  • carbon dioxide
  • sulfur oxides (impurities)

Incomplete: (some atoms in fuel are not fully oxidised)

  • water (all H atoms are completely oxidised to water)
  • carbon
  • carbon monoxide
  • unburned hydrocarbons
  • sulfur oxides (SOx)
  • nitrogen oxides (NOx)
29
Q

What are some issues arising from the production of pollutants from burning fossil fuels (alkanes)?

A
  • sulfur and nitrogen oxides cause acid rain when dissolved in water which makes water supplies too acidic for some aquatic wildlife to survive, and damages buildings and statues
  • carbon monoxide is toxic
30
Q

How can a catalytic converter be used to solve some problems caused by burning hydrocarbons?

A

Converts toxic gases (eg. CO, unburned hydrocarbons, NOx) into less toxic gases (eg. H2O, CO2, N2) - but still dangerous/contribute to global warming
(The honeycomb structure of the catalytic converters increases the surface area and allows gases to flow through)

31
Q

What is a alternative fuel to fossil fuels, and what does it entail?
(Alternatives are needed due to the depletion of natural resources and global warming and climate change)

A

Biofuel: biodiesel and biethanol (alcohol) - derived from renewable resources (living matter which has died recently) + contribute less to global warming, but uses a lot of land and lots of energy required for manufacture + transportation
Biodiesel: made from natural oils (eg. animal fats, vegetable oils)
Bioethanol: derived from sugarcane, wheat, corn and biomass - but has to be blended with fossil fuels (petrol), so only compatible with selected petrol cars

32
Q

What does carbon neutral mean?

A

No net release of carbon dioxide into the atmosphere - the rate carbon dioxide is released from combustion, equal to the rate it is taken back in by plants by photosynthesis

33
Q

Describe the process of free radical substitution

A

Free radical substitution - alkanes are generally very unreactive, but under right conditions (UV) alkanes will undergo substitution reactions
( products formed will be the alkane with one less hydrogen and a halogen to substitute ) - any hydrogen can be substituted so different structures/mixture of products will actually form)
INITIATION - the halogen (eg. Cl2) will form two free radicals (species with unpaired electron) through homolytic fission of a covalent bond (bond breaking) (remember to write under UV on the arrow) - these are highly reactive (can be shown by two half head arrows - movement of one electron)
PROPAGATION - alkane + free radical —> alkane radical + hydrogen halide (Remove a hydrogen to produce a free radical, then add the halogen)
alkane radical + halogen —> desired product + free radical
(Chain reaction - continued use of products to repeat reaction or carry out further substitutions)
TERMINATION - combining free radicals to end reaction

34
Q

How do multiple free radical substitutions work?

A

Eg. Difluoroethane, trifluoroethane, tetra-
Propagation occurs in pairs, so need a new pair for each substitution
By-product will always be eg. HF or HCl (so will need eg. 2HF, 3HF for multiple substitutions)
Hydrogens decrease as the halogen atoms in the product increase

35
Q

How would you show that eg. 2-chloropropane has been made (in free radical substitution)

A

Use structural formula and show the radical and chlorine on the desired carbon atom

36
Q

Why are alkenes more reactive than alkanes?

A

They contain a double bond so have a pi bond which is a sideways overlap of p-orbitals which is weaker and less effective than end-on overlap sigma bonds (as there is a smaller overlap between the orbitals). This breaks first.
(Need to know diagram for pi bonds)

37
Q

What is an electrophile?

A

An electron pair acceptor (an electron-deficient chemical - positive ion, or delta +, or just electron deficient)

38
Q

What is the most stable carbocation?

A

Tertiary carbocation - the carbon with the positive charge is bonded to three other carbon atoms

39
Q

What’s the difference between minor and major products?

A
  • For unsymmetrical alkenes in electrophilic addition there will be two possible products
  • Both will be made, but majority is the major product
  • major product = the most stable carbocation
40
Q

Why are addition polymers unreactive?

A

The carbon chain is saturated (single bonds) and the side chains are usually non-polar - makes disposal of polymers a challenge (as well as their formation of harmful combustion products when burnt, and non-biodegradability)

41
Q

Define volatility and viscosity and how they differ between short and long chain alkanes

A

Volatility - how easily it evaporates (short chain alkanes are more volatile than long chain alkanes as they have a lower boiling point)
Viscosity - how easily it flows (short chain alkanes flow more easily than long chain alkanes - they are quite thin/runny)

42
Q

What do you need to consider when comparing fuels?

A
  • renewability / finite resources
  • land use
  • energy (due to manufacturing + transportation)
  • carbon neutrality
  • production of toxic gases
  • yield (eg. how long will it take to produce the same amount)
43
Q

Describe the bonding in alkenes

A

Alkenes have a double bond which is made up of a sigma bond and a pi bond.
A sigma bond is a covalent bond formed when electron orbitals overlap end-on (axially)
A pi bond is a covalent bond formed when electron p-orbitals overlap sideways
A pi bond is weaker than a sigma bond as due to the smaller overlap, but when with a sigma bond it is much stronger, so double bonds are stronger than single bonds.

44
Q

Describe a real life use for an alkene reacting with H2 in the presence of a nickel catalyst to form an alkane

A

The manufacture of margarine by catalytic hydrogenation of unsaturated vegetable oils

45
Q

Define heterolytic fission

A

Unequal sharing of the electrons in the covalent bond when it breaks (both electrons shift to one of the atoms and forms two ions - one with a ‘lone pair’ of electrons showing) - presented with a full headed arrow from the bond to the atom

46
Q

Define polymer

A

A chain of monomers

47
Q

What can waste polymers be used for, and what are the pros and cons?

A
  • recycling
  • incineration to release energy
  • use as a chemical feedstock for cracking

PROS

  • all reduce landfill
  • incineration releases energy which can generate electricity
  • recycling decreases use of crude oil

CONS

  • all release toxic gases
  • all require lots of energy
  • recycling - different polymers must be separated from each other - difficult + expensive
  • incineration produces CO2 which is greenhouse gas, CO if incomplete combustion, polymers containing chlorine (eg. PVC) release hydrogen chloride gas (toxic)
48
Q

How do chemists limit the problems caused by polymer disposal?

A
  • they develop biodegradable polymers

- they remove toxic waste gases caused by incineration of plastics

49
Q

Are halogenoalkanes reactive, and why/why not?

A

They are reactive (unlike alkanes) due to the high electronegativity of the halogen. This makes the molecule slightly polar. (The delta + carbon attracts nucleophiles)

50
Q

How could you compare the rates of hydrolysis of halogenoalkanes in a practical?

A

Usually: halogenoalkane + water —> alcohol + hydrogen halide
But, water and alcohol are colourless, so difficult to tell when reaction has occurred.
Therefore use aqueous silver nitrate meaning a silver halide (insoluble) precipitate will form which will be visible. (Water still acts as a nucleophile)
Use equal amounts of each halogenoalkane, and measure the time for a precipitate to form for each one.
Ethanol must also be used, as a solvent as halogenoalkanes are insoluble in water - using ethanol ensures that the halogenoalkane dissolves so it can react with the water molecules.
Use a water bath to control a raised temperature.

Chloroalkane - white precipitate
Bromoalkane - cream precipitate
Iodoalkane - yellow precipitate

51
Q

What are the most reactive halogenoalkanes?

A
  • Iodoalkanes (react quickest/fastest rate) - due to them having the weakest bonds (C-I) (despite flouro- and chloro- having the greatest polarity due to electronegativity)
  • tertiary halogenoalkanes
52
Q

Why would a reaction be faster with KOH than with H2O?

A

This is because :OH- is a stronger nucleophile than H2O (as it is an ion and has a lone pair of electrons)

53
Q

How could you synthesise more complex (larger) compounds?

A

React (halogenoalkane) with potassium cyanide (:CN-), which increases the length of the carbon chain

54
Q

Why does halogenoalkane + ammonia need to be heated in a sealed tube?

A

Ammonia is a gas so excess ammonia gas would escape

55
Q

What is the test for a carboxylic acid?

A

Add a metal (hydrogen)carbonate (HCO3-) which will form a salt, water and carbon dioxide which is observed by fizzing (CO2), which can be confirmed by the limewater test

56
Q

What does heating under reflux involve?

A

The use of a vertical condenser held above the mixture being heated. Cool water goes in at the bottom and out at the top to condense any vapours (reagents with low bp) and stop them escaping.
This is used rather than an open test tube or distillation as the vapours need to be condensed back into the flask so the reaction can continue.

57
Q

What is an elimination reaction?

A

A reaction in which a molecule loses atoms attached to adjacent carbon atoms, forming a C=C double bond

58
Q

What is oxidation (in terms of reactions of alcohols)?

A

The loss of hydrogen from an alcohol molecule (removal of the H in the OH group and the H from the carbon atom joined to the OH group). The organic product formed contains a C=O (carbonyl group)

59
Q

Why can tertiary alcohols not be oxidised?

A

They don’t have a H adjoining the C-OH

60
Q

How can you tell if an alcohol has been oxidised?

A

Colour change from orange to green

61
Q

How can you test for purity?

A

Determine boiling temperature - impurities raise boiling temperature