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Alkene to Alkane
H2, heated, Ni catalyst
Electrophilic addition, hydrogenation
Used in the hydrogenation of vegetable oils into solid margarine (saturated fatty acid)
Alkene to diol
KMnO4(aq), H+ catalyst.
Oxidation reaction
Colour change of potassium manganate
Purple to colourless
Can use KMnO4 to distinguish between alkenes and alkanes
Alkene to alcohol
excess H2O, phosphoric acid catalyst, high pressure, high temperatures
Electrophilic addition, hydration
Alcohol to Alkene
Conc phosphoric acid catalyst, high temp and pressure
Dehydration reaction, produces multiple isomers
Alkene to halogenoalkane
HX or X2, not aqueous i.e. using gaseous HX
Electrophilic Addition, halogenation
Halogenoalkane to alkene
NaOH(eth), reflux
Produces alkene, water and NaX
Acid-base reaction, elimination reaction
Alkane to halogenoalkane
X2, UV radiation
Free radical substitution
Halogenoalkane to amine
Concentrated ethanolic ammonia, heated in a sealed container
Nucleophilic substitution
Halogenoalkane to nitrile
KCN(eth), reflux
Nucleophilic substitution
Halogenoalkane to alcohol
NaOH(aq), reflux
or H20(l), warm
Nucleophilic substitution
Alcohol to halogenoalkane
Cl: 1,2 PCl5 or 3 conc HCl, both at rtp
Br: NaBr + conc H2SO4 → HBr. warmed
I: Phosphorus and iodine, produces side product of H3PO3, under reflux
Alcohol to aldehyde/ketone
Potassium Dichromate, acid, distillation with addition.
Alcohol added drop by drop as reaction is very exothermic
Oxidation
Aldehyde/Ketone to Alcohol
Using Grignard reagent
Reduction
Aldehyde/Ketone to Carboxylic acid
Potassium dichromate, acid, reflux
Oxidation
Carboxylic acid to alcohol
LiAlH4(dry ether)
Reduction, straight from carboxylic acid to alcohol as the aldehyde formed is easily reduced down to an alcohol
Alcohol to ester
RCOOH, acid catalyst or RCOCl, rtp
Acyl chloride method is non-reversible and much faster (does not require catalyst)
Esterification
Ester to alcohol
Acid hydrolysis, H20 with acid catalyst, reflux
Alkali hydrolysis, NaOH, reflux then acid to convert carboxylate salt
In alkali conditions, the OH- is the reactant, in acidic acid is just the catalyst
Carboxylic acid to Acyl chloride
PCl5
Acyl chloride to Carboxylic acid
H2O
Aldehyde/ketone to hydroxynitrile
HCN/KCN (aq), reflux
Nucleophilic addition
Nitrile to carboxylic acid
Acid/Alkali hydrolysis. Reflux
Produces carboxylic acid/ carboxylate salt and ammonium/ammonia
Amide to carboxylic acid
Acid and Alkali hydrolysis. Reflux
side product of amine
Acyl chloride to amide
conc NH3 or RNH2
Amide to amine
acid/alkali hydrolysis or LiAlH4(dry ether). Reflux
side product of carboxylic acid
Amine to amide
Acyl chloride
Addition-elimination reaction
Nitrile to amine
LiAlH4 (dry ether)
or
Add hydrogen with a Nickel catalyst, at 150C
Reduction
Nitrobenzene to phenylamine
Sn + conc HCl, reflux. Produces a phenylammonium ion.
NaOH(aq), converts it into a phenylamine
Reduction reaction
Benzene combustion
Typically incomplete combustion, produces a sooty flame, due to high carbon to hydrogen ratio
Benzene to phenylketone
RCOCl, AlCl3 catalyst(electrophile maker)
electrophilic substitution
Benzene to nitrobenzene
conc HNO3, conc H2SO4 catalyst
electrophilic substitution
benzene to halogenobenzene
X2, FeX3 catalyst (called a halogen carrier)
Benzene does not readily react with bromine water. Evidence against Kekulé’s structure
electrophilic substitution
Benzene to alkyl benzene
RCl, FeCl3 catalyst (called a halogen carrier)
electrophilic substitution
Phenol to Tribromophenol
Br2(aq). N.B. Bromination of benzene requires liquid bromine
electrophilic substitution
Test for alkene
Bromine water
Positive test = brown to colourless
Negative test = remains brown
Test for aldehyde only
Ammonia and silver nitrate (Tollen’s)
First add mix dilute sodium hydroxide with silver nitrate
Add ammonia to dissolve solid silver(I) oxide, then add to suspected aldehyde
Positive test = Silver mirror (solid silver)
Negative test = colourless solution
or
Benedict’s Reagent
Positive test = blue solution to red brick precipitate (Cu(II) complex to Copper(I) oxide)
Negative test = remains blue
Test for carbonyls
2,4 - DNPH
Positive test = Orange precipitate
Negative test = orange solution
Then collect and recrystallise precipitate.
Take melting point, compare the value to data book values
Test for primary, secondary alcohols and aldehydes
Acidified potassium dichromate
Positive test = Orange solution to green solution
Negative test = remains orange
Test for phenols
Bromine (aq/l)
Positive test = Bromine decolourises, white precipitate forms
Negative test = brown solution
Test for organic acids
Sodium carbonate (s or aq)
Positive test = effervescence
Negative test = colourless solution
Test for methylketones
Add Iodine and alkali e.g. sodium hydroxide
Yellow precipitate forms, CHI3
Side products, carboxylate salt, water, iodide
How to prepare Grignard reagent
By adding Mg to R-Br
Warm in water bath and reflux
Grignard Reagent with water
Alkane forms, need to store Grignard reagent in dry ether
Grignard Reagent with carbon dioxide
Forms R-COOMgBr
Then add dilute acid
R-COOMgBr +H2O —→ R-COOH + Mg(OH)Br
Grignard reagent with methanal
Add Grignard reagent, R-Mg-Br then dilute acid
Form R-CH2OH, a primary alcohol
Grignard reagent with an aldehyde
Add Grignard reagent, R-Mg-Br then dilute acid
Form R-R’-CHOH, a secondary alcohol
What is an alkyl group, what is an aryl group
Alkyl - functional group derived from an alkane
Aryl - functional group derived from an aromatic ring
Purpose of anti-bumping granules
Provides small for small bubbles to form on
Prevents violent boiling
Importance of washings
When transferring between containers.
Important to rinse out containers (beakers, measuring cylinder, glass rod) and transfer these washings to the next flask
How to remove alcohol from the organic layer in a separating funnel
Add calcium chloride which reacts with the alcohol pushing it to the aqueous layer
How to remove water from a product
Drying agent e.g. anhydrous magnesium sulfate
Absorbs any remaining water, causing powder to clump.
This residue can be easily removed the pure organic liquid
Key things to remember when using a burette
Rinse burette out with solution being used for the titration
Remove the funnel before titration
Ensure jet space below the tap is filled with fluid
Use a white tile on the conical flask for a clear colour change
Add solution from burette dropwise near the end-point
Why is ethanol used as a solvent in the reaction between water and a halogenoalkane
The halogenoalkane(no hydrogen bonding) and water are not miscible
Ethanol is soluble in both water and halogenoalkane.
Allows the reactants to mix and react
The reactions in CP13b
Delay reaction:
Thiosulfate ions reacting with iodine.
Prevents a starch iodine complex from forming. Only forms when all of the thiosulfate has reacted.
Main reaction:
Peroxodisulfate ions with iodide ions
The reactions in CP14
Delay reaction:
phenol with bromine. Converting bromine back into bromide
Rate reaction:
Bromide, bromate and hydrogen ions reacting to form bromine and water.
End point when bromine bleaches methyl red.
Why is a minimum volume of solvent added during recrystallisation?
When a minimum volume of hot solvent is added this forms a saturated solution.
When the solution cools, it becomes supersaturated as solubility decreases. This allows the maximum mass of crystals of product to form.
Ice is used to extract the most crystals possible
What is homolytic fission
When the electrons split evenly between atoms bonded
Free radicals form
What is heterolytic fission
Electrons go to one species involved in the bond.
Ions form
When steam distillation is used
Use to separate an insoluble liquid with a high boiling point from an aqueous solution
Agitation of the liquid caused by steam passing through pushes the insoluble liquid to the surface of the mixture
The insoluble liquid boils off at a much lower temperature than its boiling temperature. Less chance of decomposition of desired product
When is fractional distillation used
When there is a small boiling point difference between compounds or when several compounds need to be separated
Fractionating beads in the column leading to the undergoing repeat distillations. Better separation, higher purity.
Units of ideal gas law equation
p - Pa
V - m3
T - Kelvin
n - mol
R - ideal gas constant of 8.31
Frequency density
Frequency / class width
Reaction between amine and halogenoalkane
If both primary, produces secondary amine and HX.
Further reaction could occur, creating a tertiary amine
A further reaction could then occur creating a quaternary ammonium ion e.g. (CH3)4N+
Optical isomers effect on light
Rotates the plane of plane-polarised monochromatic light
Why use TMS
Produces a single peak - all C and H in same environment
The peak does not overlap with other peaks
Peak is very strong, so don’t need a lot
Inert, non-toxic
Volatile, so can be easily removed from the sample