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Evaluative Coursework - Identifying Organic Compounds

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by

Chloe Sant

on 26 November 2013

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Transcript of Evaluative Coursework - Identifying Organic Compounds

Proton NMR
Number of peaks= number of proton environments
Hydrolysis of Esters
Image by Tom Mooring
Tests!
Evaluative Coursework - Identifying Organic Compounds
Bromine Water
TEST FOR ALKENES
Sodium Carbonate
TEST FOR CARBOXYLIC ACID
2,4 DNP
Tollens' Reagent
Potassium Dichromate
TEST FOR ALCOHOLS
TEST FOR ALDEHYDES AND KETONES
TEST FOR ALDEHYDES
With an excess of acidified potassium dichromate...
Primary alcohols can be fully oxidised to form carboxylic acids that are then distilled off for separation
Observations:
It goes from orange to colourless
It is an addition reaction that involves the breaking of the carbon carbon double bond to form an alkene with bromine molecules attached
The addition of a carbonate causes fizzing and effervesence as carbon dioxide is given off (observation)
When added to an aldehyde or ketone, a yellow or orange precipitate forms (confirms c=o.)
This precipitate is impure so it is filtered and recrystallised twice to produce yellow crystals.
The melting point of it is tested and compared to a database to identify the exact aldehyde or ketone.
Tollens' is reagent is a weak oxidising agent to identify aldehydes (ketones not oxidised.)

A "silver mirror" precipitate is formed around the test tube (observation)
It is only a test for primary and secondary alcohols, tertiary alcohols do not get oxidised.
Observation: primary and secondary go from orange to colourless
Forms salt, water and carbon dioxide
Functional Groups
Alcohol
Alkene
Aldehyde
Ketone
Carboxylic Acid
Ester
Acid Hydrolysis
Alkaline Hydrolysis
The ester is heated under reflux with dilute sulfuric acid (or HCl)
The ester is broken down by the water, with the acid as a catalyst.
It forms a carboxylic acid and a primary alcohol
e.g Propyl Ethanoate + Water -----> Ethanoic Acid + Propan-1-ol
Aqueous sodium (or potassium) hydroxide is refluxed with the ester.
It is a non-reversible reaction that leads to the formation of a sodium salt of the carboxylic acid.
Propyl Ethanoate + NaOH -------> Sodium Ethanoate + Propanol
Chemical shifts=type of proton environment at each peak
Solvents;
- CDCl(3)
- D(2)O fpr identifying OH or NH
Splitting Pattern = N+1 Rule
(spin spin coupling)
Relative peak areas=the proportions of protons in each environment
Full transcript