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Organic Synthesis Pathways for A-level Chemistry OCR F324

Mind map of all the organic synthesis reactions you need to know for the OCR A-level Chemistry syllabus, Unit F324

Charlotte Alsop

on 18 June 2013

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Transcript of Organic Synthesis Pathways for A-level Chemistry OCR F324


Aldehydes and Ketones
Addition of a halogen, such as Chlorine
Carried out at room temperature (25 degrees centigrade or 298K)
Nucleophilic Substitution
Add an excess of NH3
Free Radical Substitution
UV light (or temperature of 300
degrees centigrade)
Add Hydrogen gas, H2
Use a Nickel (Ni) catalyst
Temperature of 150 degrees centigrade
Add water (H2O)
Use H3PO4 catalyst
Temperature of 300 degrees centigrade
Pressure of 60 atm
Add concentration hydrochloric acid, HCl. as a catalyst
Heat the mixture
Nucleophilic substitution
Add sodium hydroxide, NaOH, to provide the OH- ions
Add concentrated sulphuric acid, H2SO4, as a catalyst
Heat the mixture
Add K2Cr2O7 (oxidising agent)
Add K2Cr2O7 (oxidising agent)
Add NaBH4 (source of hydride, H-, ions)
Add K2Cr2O7 (oxidising agent)
Acid hydrolysis
Add water, H2O
Add aqueous hydrochloric acid, HCl
Produces the constituent carboxylic acid and alcohol
Alkaline hydrolysis
Add sodium hydroxide, NaOH
Produces the sodium salt of the constituent carboxylic acid and the constituent alcohol
Add concentrated sulphuric acid, H2SO4
Heat the mixture
Amines are molecules containing a nitrogen atom - e.g. the primary amine functional group - NH2.
Amines are bases since they can accept a proton by using the lone pair of electrons on the nitrogen atom.
Amines react with acids to form salts.
Aliphatic amines may be prepared by the substitution of halogenoalkanes with excess ammonia.
Aromatic amines can be prepared by reducing nitroarenes with tin and concentrated HCl.
Azo dyes are made by reacting an aromatic amine with nitrous acid and then phenol in alkali.
Carboxylic acids
Carboxylic acids are found widely in nature. They are weak acids with the functional group -COOH. Carboxylic acids with between one and four carbon atoms are very soluble in water. The highly polar C=O and O-H bonds allow carboxylic acid molecules to form hydrogen bonds with water molecules. As the number of of C atoms in the carboxylic acids increases, the solubility decreases.
They react with metals to form a salt and hydrogen. They react with bases to for a salt and water. They react with carbonates to form a salt, water and carbon dioxide. The salts formed from carboxylic acids are known as carboxylates.
Aldehydes and Ketones
Aldehydes and Ketones can be detected using the reagent 2,4-DNPH. A solution of 2,4-DNPH in a mixture of methanol and sulfuric acid is called Brady's reagent. When this is added to an aldehyde or a ketone, a yellow or orange precipitate forms.
You can distinguish between aldehydes and ketones by using Tollen's reagent. Tollen's reagent is a weak oxidising agent made by adding NaOH(aq) to aqueous silver nitrate to form a brown precipitate of silver oxide, then adding dilute NH3(aq) until the precipitate dissolves.
Aldehydes can be oxidised to for carboxylic acids, and so will react with Tollen's reagent, producing a 'silver mirror'. (The aqueous Ag+ ions have been reduced to silver metal, Ag(s).) Ketones cannot be oxidised so do not produce a silver mirror.
It is possible to positively identif the carbonyl compound by:
Filtering and recrystallising the impure 2,4-DNPH derivative, which are filtered and allowed to dry. The melting point of this derivative is measured and recorded. It can then be compared to a database or a data table, in order to identify the original aldehyde or ketone.
Esters have many uses, both industrially and in catering. Esters are responsible for the flavour of many foods and the pleasant smell of flowers.
It can be prepared by reacting an alcohol with a carboxylic acid. However by reacting an acid anhydride (rather than a carboxylic acid) with an alcohol. You can also prepare esters. This method has a much higher yield of the ester than the reaction between a carboxylic acid and an alcohol.
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