4.2 Alcohols, Haloalkanes And Analysis Flashcards
Alkane to alkene?
Cracking
Alkene to alkane?
Hydrogenation
Ni H2
Alkane to haloalkane?
Radical substitution
Alkene to haloalkane?
Halogenation/electrophilic addition
HBr or Br2
Alkene to polymer?
Addition polymerisation
Alkene to alcohol?
Hydration
Steam
H3PO4
Alcohol to alkene?
Dehydration
Heat
H3PO4
Haloalkane to alcohol?
Hydrolysis
NaOH
Heat
Alcohol to haloalkane?
Halide substitution
NaBr
H2SO4
Alcohol to ketone?
Secondary alcohol oxidisation
Cr2O7-
H+
Reflux
Alcohol to aldehyde?
Primary alcohol oxidation Cr2O7-
H+
Distil
Alcohol to carboxylic acid?
Primary alcohol oxidation
Cr2O7-
H+
Reflux
Carboxylic acid to ester?
Esterification
Unsaturated hydrocarbon test
Bromine water, shake, bromine water decolourises
Test for haloalkane
Silver nitrate, ethanol and water
Tests for carbonyl?
Acidified potassium dichromate, fehlings solution, tollens reagent
Results when adding acidified potassium dichromate to test for functional group?
Ketones- no change
Aldehydes go from orange to green
Results after adding fehlings solution to test for functional group
Ketones no change
Aldehydes-dark red precipitate
Results after adding tollens reagent to test for carbonyl
Ketones- no silver mirror
Aldehydes-silver mirror
Tests for carboxylic acid?
Universal indicator or ph probe
Reactive metal
Or metal carbonate
What does universal indicator do in carboxylic acid?
pH of weak acid
What does a reactive metal do when afford to carboxylic acid?
Hydrogen effervescence
What does a metal carbonate do when added to carboxylic acid?
Co2 effervescence
Test for alcohol functional group
Warm with an equal volume of carboxylic acid and a few drops of H2SO4
Sweet smell
Define dehydration
A chemical reaction in which water molecules are eliminated from an organic compound
Define elimination
Organic reaction in which one reactant forms two products, usually a small molecule like water is released
What is nucleophilic substitution?
A chemical reaction in which an atom or a group of atoms is exchanged for a nucleophile
Why are there still CFC concerns even though they are banned?
There are other ozone depleting substances
They take many years to reach the ozone layer
They are not banned everywhere
What makes CF3Cl a suitable propellant?
Gas Volatile Nontoxic Non flammable Unreactive Liquified under pressure
How can we get rid of polymer waste?
Landfill Combustion Reusing Recycling Organic feedstock
Which alcohols are soluble?
Methanol
Ethanol
Propanol
How do you make a aldehyde with oxidation?
Gentle heating
How do you make a carboxylic acid with oxidation?
Heating under reflux
Excess potassium dichromate
How do you make a ketone with oxidation?
Heat under reflux
What is hydrolysis?
A chemical reaction in which water is a reactant.
There are alkali hydrolysis reactions where -OH is the reacting species
How can you measure the rate of hydrolysis?
Measure halide ions but looking at coloured precipitated when acidified silver nitrate is added
Measure how long it takes to form
Initiation step of homolytic fission of C-Cl bonds
C2F2Cl2 -> C2F2Clr + Cl
Propagation steps of chlorine radicals
Clr + O3 -> RClO + O2
RClO + O3 -> Clr + 2O2
Steps of nitrogen monoxide decomposing ozone
RNO + O3 -> rNO2 + O2
RNO2 + O -> rNO + O2
What is distillation?
A technique used to separate miscible liquids or solutions
What is reflux?
A technique used to stop reaction mixtures boiling away into the air
What two factors affect the reactivity of hydrolysis reactions of haloalkanes?
- Strength of the C-X bond (larger atoms = stronger shielding= easier to break)
- Polarity of the C-X bond (polarity decreases down the group)
Colour of AgCl
white
Colour of AgBr
cream
Colour of AgI
yellow
Which haloalkane has the highest rate of hydrolysis?
C-I because the bond is weakest and easiest to break
What do you need when investigating the speed of hydrolysis of haloalkanes?
ethanol as solvent
AgNO3
Common drying agents
CaCl2 and MgSO4
6 ways to separate compunds
Distillation Solvent extraction Washing Drying Filtration Recrystallisation
Describe recrystallisation
Product dissolved in minimum volume of hot solvent Filter (removes insoluble impurities) Cool Crystals should form Filter to remove soluble impurites
Describe melting point determination
- place solid in capillary tube
- place in liquid which has a biling point above our solids melting point
- place alongside thermometer and watch how melting occurs
- compare MP to known value
Describe boiling point determination
Measure BP
Impurities would increase this
What are the three types of distillation?
Simple
Steam
Fractional
Describe steam distillation
-separates insoluble liquid from aqueous solution
-steam lowers BP of immiscible liquid and causes it to evaporate and condense
WE GET A MIXTURE OF IMMISCIBLE LIQUID AND WATER
Test for unsaturated hydrocarbon
Few drops of bromine water and shake
Bromine water will become decolourised
Orange brown - colourless
Test for haloalkanes
Silver nitrate
Ethanol
Water, different colour precipitates due to AgX being formed
First test for carbonyl group
acidified potassium dichromate goes orange to green with aldehydes
orange solution with dichromate (VI) ions is reduced to a green solution containing chromium (III) ions
Last test for carbonyl group
Fehlings solution, aldehydes go dark red (from blue)
The blue copper (III) ions are reduced to give a precipitates of copper (I) oxide
What does degree of vibration depend on?
- Bond strength (stronger = higher frequency)
- Bond length
- Mass of atoms
Applications of IR spectroscopy
- Breathalysers (-OH functional group)
- Air quality (levels of pollutants, such as CO and NO are measured)
- Forensics (chemicals present at crime scenes, fuels, accelerants, plastics)
What are absorptions in the fingerprint region caused by?
Bending rather than stretching
How do you determine relative molecular mass with mass spectrometry?
By looking at the molecular ion peak
What is the m+1 peak?
Appears in the presence of C-13
Appear in more significant percentages in larger molecules
Uses of mass spec outside the lab
breathalysers
monitoring air pollution
MOT emission testing
Conditions for yeast fermentation
anaerobic
aqueous
temp range 25-40 degrees
Whats reduced in the oxidation of alcohols?
Cr (VI) to Cr3+