Chapter 12 Alkanes Flashcards

1
Q

What are alkanes?

A

Saturated hydrocarbons which contain carbon and hydrogen atoms only, joined together through C-C single bonds

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2
Q

How are the atoms in an alkane bonded together?

A

Each carbon atom is joined to four other atoms by single covalent bonds known as sigma bonds σ.
Each carbon atom has 4 sigma bonds.

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3
Q

What is a sigma covalent bond (σ)?

A

A sigma bond is the result of the overlap of two orbitals, one from each bonded atom. Each overlapping orbital contains one electron, so the sigma bond has 2 electrons which are shared between the bonding atoms. The sigma bonds are positioned on a line directly between two bonding atoms.

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4
Q

What happens to the boiling point of straight chain alkanes?

A

The boiling points will increase as the Carbon chain gets longer due to the London forces between the molecules. This is because the number of atoms in the chain increases so there are more electrons in the molecule which increases the strength of the London Forces providing a higher boiling point as a larger amount of energy is required to overcome the bonds.
Additionally, as the chain length increases the alkanes will have a larger surface area so there is more surface contact between the molecules increasing the strength of the London Forces.

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5
Q

What does the overlap of Sigma covalent bonds allow in alkanes?

A

Allows free rotation

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6
Q

How do Branched isomers affect the boiling point of alkanes?

A

Branched chain isomers have the same number of electrons, however they have a lower boiling point than straight chain alkanes, this is because branching reduces the surface contact between the molecules. Therefore, the London forces are weaker and don’t require a lot of energy to be overcome.

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7
Q

Why are alkanes unreactive?

A

The C-C and C-H σ covalent bonds are strong, they have high bond enthalpies
C-C bonds are non-polar
The electronegativity of Carbon and Hydrogen is similar so it is also considered non-polar.
Therefore, the σ bonds are low in polarity.

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8
Q

What does the complete combustion of alkanes produce?

A

When alkanes burn in a plentiful supply of oxygen, carbon dioxide and water is produced.

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9
Q

Why are alkanes useful as fuels?

A

Readily available
Easy to transport
Burn in a plentiful supply of oxygen without releasing toxic products

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10
Q

What does the incomplete combustion of alkanes produce?

A

When alkanes burn in a limited supply of oxygen carbon monoxide or carbon and water is produced.

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11
Q

What do alkanes react with halogens in the presence of?

A

UV light provides the initial energy for a reaction to take place.

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12
Q

What mechanism do alkanes proceed through?

A

Free radical substitution

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13
Q

What are the stages of Free radical substitution?

A

Initiation
Propagation
Termination

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14
Q

What happens during the initiation stage of Free radical substitution?

A

Initiation- UV light provides the energy required to break the covalent bond of the halogen via Homolytic fission. Both of the bonded atom will take one of the shared pair of electrons each, so two free radical will be formed.

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15
Q

What happens during the two propagation stages of Free radical substitution?

A

The free radicals are used up and regenerated
First propagation step: the halogen radical reacts with the C—H bond in the alkane, forming a new radical and another molecule.
Second propagation step: the new radical that was formed reacts with another halogen molecule forming an organic product and a halogen radical.
The propagation step is terminated when two free radical collide.

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16
Q

What happens during the termination stage of Free radical substitution?

A

Two radicals collide forming a stable molecule and stopping the reaction.

17
Q

Write the chemical equation for the complete combustion of octane.

A

C8H18 + 12.5 O2 ——> 8CO2 + 9H2O

18
Q

What are the problems when alkanes undergo incomplete combustion?

A

Carbon monoxide or Carbon (soot particulates) is produced

19
Q

What is the problem of Carbon monoxide?

A

Toxic gas

20
Q

What is the problem of Carbon (soot)?

A

Can irritate the respiratory system

21
Q

What type of reaction occurs between the alkane and halogen?

A

Substitution reaction as the one of the hydrogen atoms in the alkane is substituted by a halogen.

22
Q

Write the equation for the substitution reaction between ethane and chlorine.

A

C2H6 + Cl2 —-> C2H5Cl + HCl

23
Q

Write the equation for the substitution reaction between propane and chlorine.

A

CH3CH2CH3 + Cl2 —-> CH3CH2CH2Cl + HCl
Or
CH3CH2CH3 + Cl2 —-> CH3CHClCH3 + HCl

24
Q

What are the issues concerned with the substitution reaction between alkanes and halogens?

A

The substitutions can occur anywhere along the carbon chain, so multiple isomers may be synthesised
If a halogen is in excess than further substitution will occur until all the Hydrogen atoms have been substituted by the halogen.
Therefore, it is not a good synthetic method to produce a single organic compound.

25
Q

What is the problem of an excess halogen in the propagation stage of Free radical substitution?

A

If the halogen is in excess than further substitution can take place, which can continue until all the Hydrogen atoms have been substituted.
Therefore, it is not an ideal method if you only wanted to synthesis one organic product.

26
Q

Explain the Free Radical substitution of the Bromination of Methane.

A

Initiation- Br2 ——> 2Br ⚫️ (radicals created)

Propagation- Br⚫️ + CH4 ——> CH3⚫️ + HBr
Br2 + CH3⚫️ ——> CH3Br + Br⚫️ (radicals are used and than regenerated)

Termination- Br⚫️ + Br⚫️ —-> Br2
Br⚫️ + CH3⚫️ ——> CH3Br
CH3⚫️ + CH3⚫️ ——> C2H6 (Radicals removed)

27
Q

Write the overall equation for the bromination of methane.

A

CH4 (g) + Br2 (l) —-> CH3Br (g) + HBr (g)

28
Q

Demonstrate the further substitution of the Bromination of methane

A

If excess Bromine is present than further substitution can occur:

Dibromomethane- Br⚫️ + CH3Br —-> CH2Br⚫️ + HBr
Br2 + CH2Br⚫️ ——> CH2Br2 + Br⚫️

Tribromomethane- Br⚫️ + CH2Br2 —-> CHBr2⚫️ + HBr
Br2 + CHBr2⚫️ ——> CHBr3 + Br⚫️

Tetrabromomethane- Br⚫️ + CHBr3 —-> CBr3⚫️ + HBr
Br2 + CBr3⚫️ ——> CBr4 + Br⚫️

29
Q

State how the final product of a free radical substitution reaction can be separated

A

By separating individual haloalkanes by fractional distillation

30
Q

What are the reactants and products of the propagation steps in free radical substitution?

A

The reactants will always have a stable molecule and free radical
The products will also have a stable molecule and a free radical

31
Q

How would you prevent excess halogen from continuing to substitute the reaction?

A

Ensuring that the alkane is in excess

32
Q

State two reasons why it is difficult to produce a single organic product from the radical substitution of alkanes.

A

Substitution can occur anywhere along the Carbon chain
Further substitution is possible if halogen in excess

33
Q

By 2020, the EU has regulated that a car must emit less CO2 per kilometre than in 2015. A typical car will need to emit 5.6 x 10^5g less CO2 in 2020, compared with 2015.
Calculate how much less petrol would be consumed by a typical car in 2020 to meet this regulation.
Give your answer in litres of petrol (1 L of petrol has a mass of 700 g)
Assume that petrol is liquid octane, and that complete combustion takes place as in the equation below :
C8H18 + 12.5O2 —-> 8CO2 + 9H2O

A

Moles= mass/Mr
Mole of CO2 reduced= (5.6 x 10^5)/ 44= 12727.27
12727.27/ 8= 1590.91 reduced mole of petrol - use equation
1590.91 x 114= 181363.74g mass of petrol reduced
181363.74/700= 259 litres

34
Q

What is the shape around the central Carbon atom of an alkane?

A

Tetrahedral
Bond angle 109.5
This is because there are 4 electron pairs, no lone pairs.
Electron pairs repel, bond pairs repel equally and lone pairs repel more.

35
Q

Suggest how the C—C—C bond angle in cyclopropane would differ from the C—C—C bond angle in propane

A

The cyclopropane bond angle would be smaller at 60 degrees while propane have a bond angle of 109.5 degrees.

36
Q

When cyclohexane reacts with chlorine under UV light, how many di-substituted halogenycyclohexane isomers could be made?

A

4

37
Q

If you wanted to synthesise the mono-substituted molecule bromocyclopentane C5H9Br, why would you avoid using a radical substitution process to synthesise it?

A

Because substitution can occur anywhere along the carbon chain
It is costly and time consuming to separate