12- Alkanes Flashcards

1
Q

What are alkanes?

A

-main components of natural gas, crude oil
-amongst the most stable organic compounds
-lack of reactivity has allowed crude oil deposits to remain the the earth for millions of year

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2
Q

What are alkanes mainly used as?

A

fuels, exploiting their reaction with oxygen to generate heat

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3
Q

What is the general formula of alkanes?

A

CnH2n+2.

(double carbon number and add two to get hydrogen number)

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4
Q

What are the properties of alkanes we look into?

A

-Bonding
-Shape
-Variations in boiling points
-Effect of chain length on boiling points
-Effect of branching on boiling point

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5
Q

What is the bonding in alkanes?

A

-saturated hydrocarbons, containing only carbon and hydrogen atoms joined together by single covalent bonds
-each carbon atom is joined to four other atoms by a single covalent bond called a sigma bond (σ)
-σ bond is the result of the overlap of two orbitals, one from each bonding atom. Each overlap contains 1 electron, so σ bond has 2 electrons that are shared between the bonding atoms
-σ bond is positioned on a line directly between bonding atoms
-each carbon atom has 4 σ bonds (C-C or C-H)

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6
Q

What is the shape of alkanes?

A

-each carbon atom is surrounded by 4 electron pairs in 4 σ bonds which all repel each other
-repulsion results in a 3D tetrahedral arrangement around each atom
-each bond angle is approx 109.5°
-the σ bonds act as an axes around which the atoms can rotate freely, so the shapes are not rigid nut distance between bonds remains relatively the same
-evenly spaced carbon and hydrogen atoms

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7
Q

What is crude oil, how is it separated?

A

-contains hundreds of different alkanes
-oil refiners separate the crude oil into different fractions by fractional distillation in a distillation tower
-each fraction contains a range of alkanes
-this is possible due to the range of boiling points of different alkanes

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8
Q

What are the variations of boiling points of alkanes?

A

-all alkanes have different boiling points
-the greater the intermolecular forces (londons forces) the higher the boiling points
-once the forces are broke the molecules move apart from each other and the alkanes become a gas

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9
Q

In alkanes how does the length of the chain effect the boiling point?

A

-as the chain length increases, the molecules have a large surface area so more surface contact is possible between molecules
-the longer the chain = the greater the londons forces so more energy is required to overcome the forces

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10
Q

In alkanes how does branching have an effect on the boiling point?

A

-branched isomers of alkanes have lower boiling points then straight chain isomers
-the more branching there is = the fewer the surface points of contact between molecules, giving fewer lands forces
-the branches get in the way and prevent branched molecules getting as close together as straight chain molecules, decreasing the intermolecular forces further

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11
Q

What are the reasons for the lack of reactivity of alkanes?

A

-C-C and C-H σ bonds are strong
-C-C bonds are non-polar
-the electronegativity of carbon and hydrogen is so similar that the C-H bond can be considered to be non-polar

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12
Q

Why are alkanes used as fuels?

A

-give out heat
-readily available
-easy to transport
-burn in plentiful supply of oxygen without releasing toxic fuels

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13
Q

What is the equation that is used to balanced the complete combustion of alkanes?

A

CxHy + (x + y/4) O2 → xCO2 + y/2 H2O

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14
Q

What happens in the complete combustion of alkanes?

A

-react with a plentiful supply of oxygen to produce CO2 and H2O

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15
Q

what is the equation for the complete combustion of methane?

A

CH4 + 2O2 → CO2 + 2H20

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16
Q

What is the equation for the complete combustion of ethane?

A

C2H6 + 3.5 O2 → 2CO2 + 3H2O

17
Q

What is the equation for the complete combustion of hexane?

A

C6H14 + 9.5 O2 → 6CO2 + 7H20

18
Q

What happens during incomplete combustion of alkanes?

A

-limited supply of oxygen so alkanes burn incompletely
-forms carbon monoxide or soot (carbon itself)

19
Q

What is the complete combustion and also the incomplete combustion to form CO and C in heptane?

A

Complete combustion (CO2 formed) - C7H16 + 11O2 ➝ 7CO2 + 8H2O
Incomplete combustion (CO formed) - C7H16 + 7.5 O2 ➝ 7CO + 8H20
Incomplete combustion (C formed) - C7H16 + 4O2 ➝ 7C + 8H2O

20
Q

Where is a limited supply of oxygen most common?

A

In closed spaces: car engines, faulty heating systems, inadequate ventilation in living areas

21
Q

What is the reaction of alkanes with halogens?

A

-only react with halogens in the presence of ultraviolet radiation
-UV light provides the initial energy for a reaction to take place

22
Q

What is the reaction of methane with bromine?

A

-substitution reaction
-hydrogen atom is substituted by a halogen atom

CH4 + BR2 → CH3Br + HBr

23
Q

What is the mechanism for the bromination of methane?

A

Radical Substitution

24
Q

What are the three stages of the bromination of alkanes?

A

Initiation
Propagation
Termination

25
Q

What happens during initiation (stage 1)? Use bromine as an example

A

-covalent bond is broken down by homolytic fission
-each atom (bromine) takes one electron from the pair forming two highly reactive (bromine) radicals
-energy for fission is provided by UV radiation

Br-Br → Br• + •Br

26
Q

What happens during propagation (stage 2)? Use bromine as an example

A

-goes through two steps, a chain reaction
-radical is used and regenerated
-radical reacts with methane forming a methane radical and a molecule of HBr
-methyl radical reacts with another Br2 forming CH3Br and a new bromine radical
-in theory propagation steps could continue until all the reactants have been used up

Step 1: CH4 + •Br → •CH3 + HBr
Step 2: •CH3 + Br2 → CH3Br + Br•

27
Q

What happens during termination (stage 3)? Use bromine as an example

A

-two radicals collide, forming a molecule with all electrons paired
-there are a number of possibilities of termination steps with different radicals in the reaction mixture
-when two radicals collide and react both radicals are removed from the reaction mixture, stopping the reaction

•Br + Br• →Br2

•CH3 + •CH3 → C2H6

•CH3 + •Br → CH3Br

28
Q

What are the limitations of radical substitution in organic synthesis?

A

Further substitution
Substitution at different positions on a carbon chain

29
Q

Why is initiation an example of homolytic fission?

A

one electron from the bond pair goes to each atom