Chemical reactions of the alkanes Flashcards

1
Q

Are alkanes reactive?

A

No - don’t react with most common reagents

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2
Q

What are the three reasons for why alkanes lack reactivity?

A

1) C-C and C-H sigma bonds are strong
2) C-C bonds are non polar
3) The electronegativity of carbon and hydrogen is so similar that the C-H bond can be considered non-polar

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3
Q

What type of reaction do alkanes undergo?

A

Combustion

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4
Q

How do alkanes combust?

A

They react with a plentiful supply of oxygen to produce carbon dioxide and water

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5
Q

What do combustion reactions give out?

A

Heat

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6
Q

Why are alkanes used as fuels? (3 reasons)

A

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

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7
Q

What do alkanes do in a plentiful supply of oxygen?

A

They burn completely to produce carbon dioxide and water - complete combustion

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8
Q

What do alkanes do in a limited supply of oxygen?

A

Hydrogen atoms are oxidised to water, but combustion of carbon may be incomplete, forming carbon monoxide and sometimes carbon itself as soot - incomplete combustion

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8
Q

Why do alkanes not react fully in incomplete combustion?

A

There isn’t enough oxygen for complete combustion

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9
Q

How many additional oxygen molecules are required for complete combustion as you descend down the homologous series?

A

1.5 oxygen molecules

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10
Q

What is the equation for complete combustion of heptane?

A

C7H16 (l) + 11O2 (g) –> 7CO2 (g) + 8H2O (l)

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11
Q

What is the equation for incomplete combustion of heptane when CO is formed?

A

C7H16 (l) + 7.5O2 (g) –> 7CO (g) + 8H2O (l)

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12
Q

What is the equation for incomplete combustion of heptane when C is formed?

A

C7H16 (l) + 4O2 (g) –> 7C (s) + 8H2O (l)

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13
Q

What do alkanes react with in the presence of sunlight?

A

The halogens

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14
Q

Why do alkanes react with halogens only in the presence of sunlight?

A

The high-energy UV radiation present in sunlight provides the initial energy for a reaction to take place

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15
Q

What is a reaction mechanism?

A

A series of steps showing how electrons are thought to move during the reaction

16
Q

What is the mechanism for bromination of methane an example of?

A

Radical substitution

17
Q

What are the three steps of bromination of methane?

A

1) Initiation
2) Propagation
3) Termination

18
Q

What happens in the initiation stage?

A

The reaction is started when the covalent bond in a bromine molecule is broken by homolytic fission - each bromine takes one electron from the pair, forming two highly reactive bromine radicals

19
Q

Where is the energy for initiation provided from?

A

UV radiation

20
Q

What is a radical?

A

A very reactive species with an unpaired electron

21
Q

How is a radical shown?

A

With a single dot to represent the electron

22
Q

What happens in the propagation stage?

A

The reaction propagates through two propagation steps, a chain reaction

23
Q

What happens in the first propagation step?

A

A bromine radical reacts with a C-H bond in methane, forming a methyl radical, and a molecule of hydrogen bromide

24
What happens in the second propagation step?
Each methyl radical reacts with another bromine molecule, forming the organic product bromomethane, together with a new bromine radical
25
What does the new bromine radical do?
Reacts with another CH4 molecule as in the first propagation step
26
Why is propagation a chain reaction?
The two steps cycle through in a chain reaction
27
When is propagation terminated?
When two radicals collide
28
What happens in the termination stage?
Two radicals collide, forming a molecule with all electrons paired
29
Why does termination stop the reaction?
When two radicals collide and react, both radicals are removed from the reaction mixture, stopping the reaction
30
What are the two limitations of radical substitution in organic synthesis?
1) Further substitution 2) Substitution at different positions in a carbon chain
31
What is further substitution?
Another bromine radical can collide with a bromomethane molecule, substituting a further hydrogen atom to form dibromomethane - further substitution can continue until all hydrogen atoms have been substituted, resulting in a mixture
32
When does substitution at different positions in the carbon chain occur?
If the carbon chain is longer - there will be a mixture of monosubstituted isomers by substitution at different positions in the carbon chain