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Chemistry > Alcohols > Flashcards

Alcohols Flashcards

1
Q

What are the 2 methods of industrially producing ethanol

A

Hydration of alkenes in the presence of an acid catalyst
Fermentation of glucose

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2
Q

What is the functional group of alcohols

A

-OH (hydroxyl group)

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3
Q

What is the general formula for alcohols

A

CnH2n+1OH

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4
Q

What is a primary alcohol

A

The carbon atom that is bonded to the -OH group is attached to one other carbon atom

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5
Q

Structural Isomers

A

Compounds that have the same molecular formula but different structural formula

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6
Q

Why do alcohols have higher boiling points than alkanes

A

There are hydrogen bonds between molecules of the alcohol which are stronger than Van der Waals forces between molecules of the alkane, so more energy is needed to separate molecules of the alcohol

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7
Q

Why are the lower members of alcohols soluble in water

A

They can form hydrogen bonds with water molecules

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8
Q

Why is methanol soluble in water

A

Methanol can form hydrogen bonds with water molecules because it has a polar -OH group

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9
Q

In an alcohol where is the hydrogen bond formed

A

Between the delta positive H atom of an alcohol molecule and the delta negative O atom of a water molecule.

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10
Q

Why are alcohols good solvents

A

They have a polar -OH group and a non-polar hydrocarbon chain so they can form both hydrogen bonds and VdW forces.

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11
Q

Why does the solubility of alcohols decrease as the Mr increases

A

As the molar mass increases, the non-polar hydrocarbon chain which is insoluble becomes larger, hence the solubility decreases.

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12
Q

What shaped molecules are non-polar and why

A

Trigonal planar
Tetrahedral
Octahedral
(and all the bonds are the same)
This is because the molecule is symmetrical and dipoles cancel

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13
Q

What shaped molecules are polar and why

A

Bent, trigonal pyrimidal or trigonal bipyrimidal
This is because the molecule in unsymmetrical and dipoles do not cancel

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14
Q

How is ethanol made by the catalytic addition of steam to ethene

A

By heating ethene with steam at 350 degrees and 60 atmospheres, in the presence of concentrated phosphoric acid as a catalyst

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15
Q

What type of reaction is the catalytic addition of steam to ethene

A

Continuous

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16
Q

Conditions needed for the catalytic addition of steam to ethene

A

High temp (350 degrees)
High pressure (60 atm)
H3PO4 catalyst

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17
Q

What type of reaction is making ethanol by fermentation

A

Batch process

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18
Q

How is ethanol made pure and separated from the reaction mixture

A

Fractional distillation

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19
Q

Reaction for fermentation

A

C6H12O6 (aq) ———–> 2C2H5OH(l) + 2CO2(g)

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20
Q

What are the conditions for fermentation

A

Yeast
Warm temperature (37 degrees)
Anaerobic conditions

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21
Q

Advantages of making ethanol by fermentation

A

Uses renewable resources such as sugarcane
Carbon neutral

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22
Q

Disadvantages of making ethanol by fermentation

A

Slow reaction with low yield
Ethanol not pure so has be separated by fractional distillation
Large areas of land needed to grow sugarcane
Low atom economy process

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23
Q

Advantages of making ethanol by catalytic addition of steam to ethene

A

Continuous process therefore higher yield
Ethanol is pure as only one product formed
Atom economy of 100%

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24
Q

Disadvantages of making ethanol by the catalytic addition of steam to ethene

A

Ethene is made from crude oil which is a non-renewable resource
Expensive as it needs a high temp and pressure
Not carbon neutral

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25
Q

What is ethanol produced by fermentation used as after being separated by fractional distillation

A

A biofuel

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26
Q

Biofuel

A

Fuel produced from a renewable resource

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27
Q

Meaning of carbon-neutral in the context of biofuel

A

The fuel is carbon-neutral as the CO2 given out when the fuel burns almost equals the carbon dioxide that was taken in from the atmosphere by the plants. As a result there is no net carbon dioxide emission to the atmosphere when this fuel is burned.

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28
Q

What is formed when an alkene reacts with steam in the presence of an acid catalyst (concentrated phosphoric acid)

A

An alcohol

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29
Q

Describe the mechanism for the formation of an alcohol when an alkene reacts with steam in the presence of an acid catalyst.

A
  1. Draw the displayed formula of the alkene, with an arrow coming from the double bond to a single H+ ion and this will form a carbocation as the double bond breaks.
  2. Draw the carbocation reacting with a molecule of H2O draw out with the partial charges and the electron pair. There will be an arrow from the electron pair on the O going to the C+ on the carbocation.
  3. The H2O all add onto where the C+ is, on top of it and the O now has a + charge.
  4. There is now an arrow coming from the middle of the OH bond , to the O+ ion.
  5. The H will the arrow coming out of it leaves as a H+ ion and leaves an alcohol with a double bond on the oxygen atom.
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30
Q

What happens when alcohols burn in air/oxygen

A

They produce carbon dioxide and water and liberate heat energy

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31
Q

What 2 other products are formed in the incomplete combustion of alcohols

A

Carbon and Carbon monoxide

32
Q

What observation can be made about the incomplete combustion of alcohols

A

Sooty flame / black smoke / black fumes

33
Q

What is formed when a primary alcohol is oxidised

A

An aldehyde

34
Q

What forms when an aldehyde is oxidised

A

A carboxylic acid

35
Q

What is formed when a secondary alcohol is oxidised

A

A ketone

36
Q

What is formed when a tertiary alcohol is oxidised

A

There is no reaction and no product as they are not easily oxidised

37
Q

What is a suitable oxidising agent

A

Acidified potassium dichromate(VI) / potassium dichromate and dilute sulfuric acid

38
Q

how do you show an oxidant in an equation where alcohols are being oxidised

A

[O]

39
Q

What do aldehydes look like

A

There is a double bond coming off the carbon with an oxygen attached and a hydrogen atom coming off another single bond from the same carbon.

Ends in -al

40
Q

What do ketones look like

A

They are always found in the middle and have just a single double bond coming off the carbon with an oxygen atom attached

ends in -one

41
Q

What do carboxylic acids look like

A

Always on the end and have a double bond coming off the carbon atom with a oxygen atom attached and a single bond also coming off the same carbon atom with an OH attached

42
Q

What is formed when a primary alcohol is oxidised

A

An aldehyde and water

43
Q

Conditions for the oxidation of a primary alcohol to make an aldehyde

A

Heat and distil off the aldehyde as it forms

44
Q

How do you ensure the maximum possible yield of the carboxylic acid is formed

A

Heat the mixture under reflux
Use excess oxidising agent

45
Q

How do you prevent further oxidation of the aldehyde to the carboxylic acid

A

Distil off the aldehyde as it forms
Use excess alcohol

46
Q

Explain how the method used to oxidise a primary alcohol determines whether an aldehyde or carboxylic acid is formed

A

Carboxylic acid :

Use excess acidified potassium dichromate instead of excess alcohol and heat the reacting mixture under reflux instead of distilling off the product.

47
Q

What happens when a tertiary alcohol is oxidised

A

It doesn’t get oxidised and so there is no change and the solution remains orange

48
Q

Describe the set-up for distillation

A

There is a round bottomed flask, whith a thermometer coming out of the top and heat being applied at the bottom ( electric heater)

The thermometer bulb should be level with the side arm leading to the condenser to measure the BP of the liquid that distils out

Attached to the flask is also a Liebig condenser, with water out on the top and water in on the bottom.

There is also a collection flask which is chilled with ice.

49
Q

Why does water go in through the bottom of the condenser

A

To go against gravity to allow more efficient cooling and keep the condenser full of water

50
Q

Why are electric heaters used to heat organic materials

A

Organic chemicals are flammable

51
Q

Describe the setup for the laboratory preparation of an aldehyde / for reflux

A

There is a round bottomed flash with an electric heater at the bottom.

There is a Liebig condenser attached vertically to the flask.

Water in at the bottom and water out at the top.

Make sure the top is open and NOT CLOSED

52
Q

Why is the collecting flask in distillation surrounded by an ice-water mixture

A

To prevent the aldehyde from evaporating as it has a low boiling point

53
Q

Which method do you use to make an aldehyde from a primary alcohol

A

Distillation

54
Q

Which method do you use to make a carboxylic acid from a primary alcohol

A

Heat under reflux and then use distillation

55
Q

What does anhydrous sodium sulphate and anhydrous calcium chloride do / act as

A

It is added to the distillate as it is the drying agent and will remove water and dry the product.

56
Q

When doing reflux, why is the end of the condenser never sealed

A

As the build up of gas pressure could cause the apparatus to explode

57
Q

Primary alcohol + [O] =

A

aldehyde

58
Q

Aldehyde + [O] =

A

Carboxylix acid

59
Q

Secondary alcohol + [O] =

A

Ketone

60
Q

Describe the test to distinguish between an aldehyde and ketone using Tollen’s reagent

A

Add Tollen’s reagent to the compound and warm.
Aldehyde - A silver mirror is formed
Ketone - There is no change. Remains colourless

61
Q

What is Tollen’s reagent

A

A mild oxidising agent, which is a solution of silver nitrate in aqueous ammonia.

62
Q

Why is the reaction of ethanal with Tollen’s reagent a redox reaction

A

Ethanal is oxidised to carboxylic acid and Ag+ ions are reduced to Ag

63
Q

Why does propanone not react with Tollen’s reagent

A

It is a ketone and cannot be oxidised by Tollen’s reagent

64
Q

Describe the test with Fehling’s solution to distinguish between an aldehyde and a ketone

A

Add Fehling’s solution to the compound and warm.
Aldehyde - A brick red precipitate is formed.
Ketone - There is no change. The solution remains blue

65
Q

What is Fehling’s solution

A

A mild oxidising agent, which contains blue copper(II) ions which oxidise aldehydes and not ketones.

66
Q

What is the reason for heating under reflux

A

Reflux allows heating for a long time without losing the volatile reactants and products. Refluxing helps speed up chemical reactions without losing the volatile reactants and products by evaporation.

67
Q

What is the function of the condenser when heating under reflux

A

It condenses the hot vapour into liquid and the liquid drips back into the flask.
This prevents the escape of volatile reactants and products and allows the reaction to continue.

68
Q

What happens and is formed when alcohols are dehydrated

A

When alcohols are dehydrated with excess hot concentrated sulfuric acid, an alkene is formed and water

69
Q

Describe what happens generally in the dehydration of an alcohol (NOT THE MECHANISM)

A
  1. First remove the -OH
  2. Then remove the H from the C next to the C attached to the -OH
  3. An alkene is formed and water
70
Q

What is formed when a secondary alcohol is dehydrated

A

A mixture of alkenes

71
Q

Why is a mixture of alkenes formed when a secondary alcohol is dehydrated

A

Dehydration involves the removal of OH and H to make water, and H can be removed from either C1 or C3 so 2 alkenes and water are formed

72
Q

Describe the mechanism for the dehydration of an alcohol

A
  1. Draw the partial charges on the O and H of the OH and the H+ ion
  2. Draw an arrow from the electron pair of the O on the OH to a H+ ion this forms just an alcohol with a + on the O and the H adds onto the O
  3. From this alcohol structure draw an arrow from the middle of the C-H on the adjacent C, to the C-C and then another arrow from the middle of the C-O bond to the O. (NORMAL ELIMINATION MECHANISM HERE)
  4. This forms an alkene and H+ and water
73
Q

What is the name of the reaction between an alcohol and HBr/Cl/I

A

Nucleophillic substitution

74
Q

What is the name of the reaction between an alcohol with K2Cr2O7 and dilute H2SO4

A

Oxidation/redox

75
Q

What is the name of the reaction between an alcohol with concentrated H2PO4 / H2SO4

A

Elimination

Chemistry (20 decks)

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