Organic practical work Flashcards
Describe how the student would prepare the standard solution, naming apparatus and method (3 marks)
- Dissolve solid in (distilled) water (less than 250 cm3) in beaker
- Transfer (solution) to volumetric flask AND Transfer washings (from beaker) to flask
- Make up to mark/up to 250 cm3 with (distilled) water AND Invert flask (several times to ensure mixing)
What does recrystallisation do
Purifies solids
What is the first step in recrystallisation
Dissolve solid in the minimum volume of hot solvent
After you’ve dissolved the solid in hot solvent when recrystallising, what is the next step
Allow the solution to cool down slowly, crystals will start to form
What is the name of the flask involved in reduced pressure filtration
Buchner
After allowing the solution to cool when recrystallising, what is the next step
Filter to remove the impurities in the solution and obtain the purified solid crystals
What is used to wash the purified crystals
Very cold solvent
Why must the solvent be cold when washing the crystals after recrystallisation
So solid product doesn’t dissolve again
What is the final step in recrystallisation
Leave crystals to dry
If a substance contains impurities, will the melting point be lower or higher than data book values
Lower
If the substance contains impurities, will the temperature range be smaller or larger than data book values
Larger range
What is the typical reaction of alkanes
Radical substitution
What is the typical reaction of alkenes
Electrophilic addition
What are the properties of alkenes
- Electron rich double bond
- Non-polar bond
What are the properties of aromatic compounds
- Delocalised electron ring
- Stable
What is the typical reaction of aromatic compounds
Electrophilic substitution
What are the 2 properties of alcohols
- Lone pair on oxygen can act as a nucleophile
- Polar C-OH bond
What are the 2 typical reactions with alcohols
- Esterification and nucleophilic substitution
- Dehydration/ elimination and nucleophilic substituion
What is the property of haloalkanes
Polar C-X bond
What is the typical reaction involving haloalkanes
Nucleophilic substitution and elimination
Properties of nitriles
Electron deficient carbon centre
Typical reaction of nitrile
Reduction and hydrolysis
Properties of amines
Lone pair on the nitrogen is basic, can act as a nucleophile
Typical reaction of amines
Nucleophilic substitution and neutralisation
Properties of aldehydes and ketones
Polar C=O bond
Typical reactions of carbonyls (3 things)
- Nucleophilic addition
- Oxidation of aldehydes
- Reduction
Property of carboxylic acids
Electron deficient carbon centre
Typical reactions of carboxylic acids
- Esterification and neutralisation
Properties of esters
Electron deficient carbon centre
Typical reactions of esters
Hydrolysis
Typical reaction of acid anhydride
Esterification
Property of acid anhydride
Electron deficient carbon centre
Typical reactions of acyl chloride
- Nucleophilic addition-elimination
- Condensation
- Friedel-Crafts acylation
Property of acyl chloride
Electron deficient carbon centre.
What 3 functional groups are involved in addition reactions
- Alkene
- Aldehyde
- Ketone
What are the 3 functional groups involved in substitution reactions
- Halogens
- Benzene (H is substituted)
- Alcohol
What 2 functional groups are involved in elimination reactions
- Halogens
- Alcohols
What 4 functional groups are involved in condensation reactions
- Acyl chloride
- Carboxylic acids
- Amides
- Alcohols
What 2 functional groups are involved in hydrolysis reactions
- Esters
- Acid anhydride
What are the 2/3 functional groups that can be oxidised
- Primary alcohol
- Aldehyde
- Secondary alcohol
What is reduction in terms of electrons
The gain of electrons
Explain how TLC could be used to monitor the course of a reaction (2 marks)
Take samples from reaction mixture at regular intervals
Spot/run on a TLC plate, alongside cyclohexanol (and cyclohexanone) controls 9
Plan an experiment to identify the pure organic ketone (3 marks)
React (sample of distillate) with 2,4-dinitrophenylhydrazine
recrystallise AND determine the melting point
Compare melting point to known/library value for
cyclohexanone (derivative)
What are the steps to purify a liquid
- Add a neutralising agent by formula or name e.g.
Na2CO3 - In separating funnel, organic layer is on top (as less dense as stated in original question
- Drying with an anhydrous salt by formula or
name, e.g. MgSO4, Na2SO4, CaCl2 - Redistil
Draw a distillation
distillation flask
heat source
thermometer at outlet (bulb level with outlet)
still-head
water condenser (correct direction of water
flow)
receiving vessel
open system.
A reactant in solution reacts to form a solid. How can the solid be isolated (1 mark)
Filtration
How can the solid be purified (1 mark)
Recrystallisation
How could the purity of the solid be checked (1 mark)
TLC or melting point measurement
How to separate a liquid product (1 mark)
Separating funnel
Organic liquid may still have some water present. How can this be removed before purification (1 mark)
By adding a (solid) drying agent (such as Na2SO4/MgSO4/CaO)
Filtering off the unwanted solid
How can the liquid be purified (1 mark)
Distillation
How could the purity of the dry liquid be checked, after purification (1 mark)
Chromatography
A reaction in aqueous solution forms a slat that is soluble in water. The aim is to isolate the acid of the salt and then purify it. The acid is a liquid that is not soluble in water. How can the acid be formed and then isolated (1 mark)
Add acid then separating funnel
How can the acid be purified (1 mark)
Distillation
How can the purity of the liquid be checked (1 mark)
Chromatography
List the equipment used in a reflux (3 marks)
Round-bottomed or pear-shaped flask (1)
Condenser (1)
Anti-bumping granules (1
How could we carry out a quick test to distinguish an aldehyde from a ketone (2 marks)
Tollens: warm with Tollens reagent (or AgNO3/NH3) (1)
Silver mirror (1)
How could we carry out a quick test to distinguish an alcohol from a ketone (2 marks)
Cr2O72-/H+ (1)
Orange to green (1)
Allow DNPH/organe ppte for (2)
How could we carry out a quick test for a haloalkane that also identifies the halide (3 marks)
AgNO3 (HNO3) (1)
NaOH (1)
White, cream or yellow precipitate (1)
(redissolves in conc. NH3 if AgBr and in dil. NH3 if AgCl)
How could we carry out a quick test for a carboxylic acid (2 marks)
Na2CO3 (1)
Effervescence (1)
How could we carry out a quick test for phenol but not benzene (3 marks)
Br2 (aq) (1)
Decolourised bromine (1)
White precipitate (1)
Esterifcation happens when an alcohol and a carboxylic acid are reacted together. The product ester will often have a boiling point above room temperature and is also often immiscible with water. Esters are typically less dense than water. Carboxylic acids and alcohols will dissolve in water, as will the catalytic acid. Write down the steps required to purify an ester, and to ensure that no alcohol, carboxylic acid or catalytic acid remain in the product (6 marks)
Separating funnel (1)
Collect non-aqueous TOP layer (1) (mark for stating product is the top layer)
Wash in funnel with aq. Na2CO3/NaHCO3 (open tap to allow gas to escape) (1)
Dry organic layer with drying agent (1)
Filter (1)
Distil (1)