Unit 4.8 - Organic synthesis and Analysis Flashcards
What type of reactions do double bond reactions tend to be?
Addition
How are addition polymers produced?
From alkenes, where the double bond id broken to form a repeating unit
Describe a polymer repeating unit
No double bond
Saturated
How should a repeating unit always be shown?
With extended bonds through the brackets showing that it bonds to other repeating units on both sides
When do condensation polymers form?
When a water molecule is removed from the species of a reaction
How are polyesters formed?
In a reaction between dicarboxylic acids and a diol (a dialcohol), producing an ester linkage
Type of linkage in a polyester
Ester
Common example of a polyester
Terylene, known as PET
What is Ethan-1, 2-diol present in?
Antifreeze
What is given off when a dicarboxylic acid and a diol produce an ester linkage in a polyester?
Water
what else can you also make an ester linkage with with an alcohol?
a dioyl chloride
another word for ethan-1,2 - diol
ethylene glycol
what would be eliminated in the reaction between a carboxylic acid and an acid chloride?
HCl
How are polyamides formed?
In a reaction between a dicarboxylic acid (or a diol chloride) and a diamine
What is the removed during the reaction to form polyamides?
A molecule of water
What is left when a molecule of water is removed during a reaction between a dicarboxylic acid (or a dioyl chloride) and a diamine?
An amide linkage
Common examples of polyamides
Nylon - 6,6 and Kevlar
Explain all of the differences between addition polymerisation and condensation polymerisation
If the monomer is an alkene, then addition polymerisation occurs
No small molecule is lost and the polymer is the only product, then addition polymerisation has occurred
If a small molecule e.g - H2Oor HCl is produced along side side the polymer then a condensation polymerisation has taken place
The monomer(s) contain function groups such as -NH2, -COOH, -OH or -COCl then condensation polymerisation occurs
The chain contains the amide link -C(O)N(H) or an ester linkage -OC(O)- then condensation polymerisation has occurred
The chain only consists of carbon atoms then addition polymerisation has occurred
Properties of addition polymerisation
The monomer is an alkene
No small molecule is lost
The chain only consists of carbon atoms
Properties of condensation polymerisation
A small molecule e.g - H2O or HCl is produced
The monomer(s) contain functional groups such as -NH2, -COOH, -OH, -COCl
The chain contains an amide link -C(O)N(H) or an ester linkage -OC(O)-
Why are many of the reaction in organic chemistry laborious?
Since when you react two organic reagents you will produce some undesired products
Impurities
Undesired products
Name for undesired products
Impurities
What will there also be when trying to form something in a reaction except for the usual impurities?
Unreacted starting materials in the mixture
Purification
For a pure sample, we need to separate the product from the mixture
Separating the product from the mixture for a pure sample
Purification
Why do many organic reactions not go to completion as required?
Other products may be produced, and some unreacted starting product may remain
What’s an important part of any organic preparation?
The separation and purification of the products
What will you also have in the reaction products when producing ethyl ethanoate?
Ethanol and ethanoic acid that’s unreacted and some water that also forms
Miscible liquids
Will mix and dissolve in each other
Liquids that will mix and dissolve in each other
Miscible
What’s important to note about the solution produced when making ethyl ethanoate?
All of the four compounds present are miscible with each other
What would we see when making ethyl ethanoate and why?
A colourless liquid
All four compounds are miscible with each other
What conditions could the products be in depending on the reaction?
Could be an insoluble solid, may be present in solution or as immiscible liquids
What does each mixtures of products after an organic reaction need?
A different method of separation
When can distillation be used to separate the products from the other substances present in the reaction mixture?
If the product does not decompose at or below its boiling temperature and the boiling temperature is not too high
What separation technique can we use If the product does not decompose at or below its boiling temperature and the boiling temperature is not too high ?
Distilllation
When can simple distillation be used to separate a product from the other substances present in the reaction mixture?
If the boiling temperature of the product differs by a reasonable amount (perhaps 20 degrees Celsius or more) from the boiling temperatures of the other compounds present
What can simple distillation also be used for?
Separating a volatile liquid from other substances in the mixture that are not volatile
What is used to separate a volatile liquid from other substances in the mixture that are not volatile?
Simple distillation
What separation technique can be used if the boiling temperature of the product differs by a reasonable amount?
Simple distillation
Example of simple distillation
The distillation of 2-chloro-2-methyl propane from its mixture with 2-methylpropan-2-oil and hydrochloric acid
When is fractional distillation used?
If the boiling temperatures are closer together
What is used to separate if boiling temperatures are closer together?
Fractional distillation
What is used during fractional distillation and why?
A fractionating column, which enables more efficient separation of the products to occur
Give 2 examples of using fractional distillation
-the separation of ethanol obtained from the fermentation of sugars is more effective if fractional distilllation is used
-the primary separation of the products present in crude oil (petroleum) is also carried out by fractional distillation
What reaction technique is used to separate compounds that decompose just before or at their boiling temperatures or have very high boiling tempatures?
Distillation is carried out under reduced pressures (vacuum distillation) or steam distillation can be used
When is distillation carried out under reduced pressures (vacuum distillation) or is steam distillation used?
For compounds that decompose just before or at their boiling temperatures or have very high boiling temperatures
What does pressure do to the boiling point of a compound?
The lower the pressure, the lower the boiling point of a compound
What is vacuum distillation?
When there’re less pressure exerted on the vapour since this decreases the compounds boiling temperature
Give an example of reduced pressure distillation working
The alkane dodecane C12H26 boils at 216 degrees under atmospheric pressure (101kpa) but at 92 degrees if the pressure is reduced to 1.3kpa
What do we need to work out when working with miscible liquids?
Which is the organic layer and which is the aqueous layer
Which layer is discarded and which layer is kept with miscible liquids?
Discard the aqueous layer
Keep the organic layer
What are the 2 methods of determining what out organic layer and what our aqueous layer is when working with miscible liquids?
Use density data
Keep adding deionised water
How do we use density data to work out which layer is an organic layer with miscible liquids?
The lower density one will be on top
Explain properly how we would use deionised water to see which layer is an organic layer with miscible liquids
Keep adding deionised water to see which layer grows
There will still be water present in the organic product, which is what we keep
In order to get a dry product (dry = no water) we should add a drying agent for example calcium chloride or magnesium sulphate, which are hygroscopic (absorb moisture)
We could then use this in fractional distillation and compare its boiling point with literature values to know that its been purified well
Drying agents \examples
Calcium chloride
Magnesium sulphate
Why are calcium chloride and magnesium sulphate examples of drying agents?
They’re hygroscopic (absorb moisture)
How can we tell if something has been purified well?
Use it in fractional distillation and compare its boiling point with literature values
Example of organic products that are sensitive to heat
Esters
What do some organic products do upon excessive heating and why?
Decompose
They’re sensitive to heat
Which separation technique do we use if organic products are sensitive to heat and decompose upon excessive heating?
Steam distillation
When do we use steam distillation?
When organic products are sensitive to heat and may decompose upon excessive heating
Which industry is steam distillation very important n?
The perfumery industry
Why is steam distillation so important in the perfumery industry?
Essential oils extracted from plants may decompose if heated to their boiling temperatures at atmospheric pressure
How does steam distillation work?
Steam is passed into the reaction mixture and the volatile compounds present pass over with steam, and condense in the receiving flask
What is one of the most widely used oils in the perfume industry? Explain how it is used
Rose oil
Steam distillation of rose oil gives an oil (containing a number of different compounds) and water from the condensed vapours
What do we look at during solvent extraction?
The solubility of a product in different solvents
What is solvent extraction?
A method that depends on the differing solubility of a compound in two immiscible solvents
Give an example of a differing solubility of a compound in different immiscible solvents
Iodine is about 90x more soluble in tetrachloromethane than in water
What happens if tetrachloromethane is added to an aqueous solution of iodine and the mixture shaken?
Most of the iodine is extracted into the tetrachloromethane layer
How do we separate 2 layers?
Using a separating funnel
What do we need to do if CO2 gas forms in a reaction that requires the use of a separating funnel?
Make sure to release pressure in the funnel periodically
What is used to separate a solid from a liquid?
Filtration
What is filtration used for?
Separating a solid and a liquid
How can filtration be carried out?
Using a filter paper and a funnel or sometimes with a plug of cotton wool to stop the solid
The use of what makes filtration quicker and why?
The use of fluted filter paper
The filtrate only needs to travel through one layer of filter paper and the paper only touches the funnel at the folds
What is fluted filter paper used for?
Making filtration faster
What’s another thing we can use for filtration?
Filtration using a Büchner funnel (vacuum filtration)
What needs to be done once the solid is in the funnel after filtration?
It needs to be washed with an appropriate solvent and dried in the air, or in a drying oven at a temperature below its melting temperature
When are the products obtained by crystallisation?
If the solid is present as a solute in solution
How are the products obtained if the solid is present as a solute in solution?
By crystallisation
Why would a solution be coloured when it’s supposed to be colourless?
Due to the presence of impurities
Why would a solution be coloured when it’s supposed to be colourless?
Due to the presence of impurities
What is used when a solution is coloured when it’s supposed to be colourless?
Decolourising charcoal
What does declourising charcoal do?
Absorbs the coloured impurities
How is decolourising charcoal used?
The solution is boiled with a little decolourisng charcoal to remove the colour and then filtered hot to remove the charcoal that contains the absorbed colour
What do we do after using decolorising charcoal?
The solution is filtered hot to remove the charcoal that contains the absorbed colour
How is a filtrate concentrated?
By boiling and is then cooled
How Dow e know that a solution has been sufficiently concentrated?
Crystals of the solute appear on cooling. These are filtered off and dried.
What does it mean if crystals of a solute appear on cooling?
The solution has been sufficiently concentrated
What is done to crystals of a solute?
They’re filtered off and dried
What does it mean mean if no crystals appear on cooling?
Then the solution needs to be made more concentrated
How do we know that a solution needs to be made more concentrated?
If no crystals appear on cooling
What type of solvent do we need to choose when extracting soluble solids from solution?
Where the solid dissolves poorly when cold but well when hot
When does extra care need to e taken when concentrating a solution?
If the solvent is flammable
What is used when concentrating a solution if the solvent is flammable?
Generally a water bath or some method of electrical heating, for example a hot plate is used