Interpretation:
A stepwise procedure with equations to show how to separate a mixture of
Concept Introduction:
Separation of the components of a mixture of organic compounds is based on the difference in their solubility in water and an organic solvent immiscible with water.
Advantage is taken of the difference in solubility of a basic (or acidic) compound and its conjugate base (or acid) in water.
Conjugate base of an acid or conjugate acid of a base are salts. Their ionic nature leads to a higher solubility in water as compared to a non-polar (or weakly polar) organic solvent. They are extracted into the aqueous phase containing an acid or a base from the solution of the mixture in a suitable organic solvent such as diethyl ether.
The base or the acid can then be recovered from the aqueous phase by neutralizing the conjugate acid (or base) with a strong base such as sodium hydroxide (or a strong acid such as hydrochloric acid). The recovered base (or acid) being insoluble separates out.
A neutral compound remains in ether solution (organic phase) from which it can be recovered by allowing ether to evaporate.
Trending nowThis is a popular solution!
Chapter 22 Solutions
Organic Chemistry - Standalone book
- Several diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be prepared from acrylonitrile.arrow_forwardShow how to convert carboxylic acids to other functional groups, and devisemultistep syntheses using carboxylic acids as starting materials and intermediates.Explain how acid chlorides are used as activated derivatives of carboxylic acidsarrow_forwardWhy is ethyl alcohol and water in liquid form an azeotropic mixture?arrow_forward
- 20. Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCI3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a reasonable mechanism for the dehydration of 2- methylcyclohexanol by POCl 3 in pyridine.arrow_forwardBenzene is often produced as a side product during Grignard reactions using phenylmagnesium bromide. How can its formation be explained? Give a balanced equation for its formation.arrow_forwardSome alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.arrow_forward
- An unknown organic compound P has a molecular formula of CaHi60. P reacts with 2,4- dinitrophenylhydrazine but not with Tollen's reagent. P also reacts with iodine in sodium hydroxide to give yellow precipitate. On reduction, compound P produces a new compound Q. On heating the compound Q with concentrated sulphuric acid produces R which decolourises bromine in tetrachloromethane. Identify P, Q and R. Explain your reasoning. 10.arrow_forwardPrimary amines can be prepared from amides by Hoffman's reaction. Write a general equation for the reaction and give reagents with reaction conditions for this reaction. What property of amines is responsible for them being basic. Suggest one way of Increasing the basicity of an amine and give a specific example of its application.arrow_forward6. The reaction between aniline and nitrous acid at low temperature yields A) an N-nitroso amine B) a diazonium salt C) a nitrile D) an amine nitrite salt 7. An organic nitrogen compound, X, gives ammonia on warming with dilute aqueous sodium hydroxide, X could be A) ethanamide B) ethylamine C) phenylamine D) amino ethanoic acidarrow_forward
- A compound of molecular formula C5H10O forms a yellow precipitate with 2,4-dinitrophenylhydrazine reagent and a yellow precipitate with reagents for the iodoform test. a) Draw the structural formulae b) Name the two (2) compounds that fit these tests.arrow_forwardShow how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoicacid, phenol, benzyl alcohol, anilinearrow_forwardpropanoic acid + methanol (in concentrated sulfuric acid)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning