Elective (analytical chemistry)_Separation and purification methods

[HKDSE_2013_q3(a)]
(a) Outline how hex-1-ene can be obtained from a mixture of hex-l-ene, octane and water by physical
methods.
(Boiling points: hex-l-ene = 63°C, octane = 125°C, water = 100°C) (4 marks)

[HKDSE_2013_q3(ci, ii)]
The main pigments in a certain brand of tomato paste are lycopene (reddish orange) and β-carotene (yellow).
In order to isolate lycopene from the tomato paste, an experiment involving solvent extraction, thin-layer
chromatography (TLC) and column chromatography was performed.
(i) The result of TLC is shown below:

Calculate the Rf value for the lycopene spot. (1 mark)

(a) Answer the following short questions:

(ii) Which of the following chemicals is most suitable for drying ethyl ethanoate ?
anhydrous magnesium sulphate, concentrated sulphuric acid, solid sodium hydroxide
(1 mark)

[HKDSE_2014_q3(c)(i)]
(c) Under room temperature, T (CxHyOz) is a colourless oily liquid and is immiscible with water.
Moreover, T does not react with NaHCO3(aq).
(i) A sample of T contains an organic acid as impurity. Outline the experimental steps for
purifying the sample by using NaHCO3(aq) and pentane.
(2 marks)

[HKDSE_2015_q3(a)(iii)]

(a) Answer the following short questions:

(iii) Suggest how copper powder can be obtained from a mixture of copper powder and iron(III) oxide
by chemical method. (2 marks)
[HKDSE_2016_q3c(ii)]
(c) X and Y are isomeric compounds with their structures shown below:

(ii) The melting point of X is 50oC while that of Y is 77oC. Both of them are insoluble in water but
soluble in dichloromethane. When treated with dilute Na2CO3 (aq), no reaction occurs for X
but reaction occurs for Y to form a soluble salt.
(1) You are provided with dilute Na2CO3 (aq) and dilute H2SO4 (aq). Outline an experimental
procedure, based on solvent extraction, to separate solid Y from a solution of X and Y in
dichloromethane.
(2) Suggest how you can identify that the solid obtained in (1) is pure compound Y.
(5 marks)
[HKDSE_2017_q3(c)(i)]

3. (c) Many plants contain useful organic compounds which can be obtained by extraction using suitable
solvents.
(i) The leaf of a certain plant contains a useful organic compound S. S can dissolve gradually in a
warm organic solvent, and can be extracted from the leaves by using this solvent.
(1) ‘Heating under reflux’ is a method commonly used to carry out this kind of extraction. State
the advantage of this method.
(2) After extraction, the solvent can be removed from the extract by simple distillation. Draw the
labelled diagram for the set-up required for this simple distillation.
(3) S obtained from the extraction may contain other organic impurities. Suggest a method for
separating S from these impurities.
(4 marks)
[HKDSE_2018_q3(c)(i)]
3. (c) A liquid mixture consists of two organic compounds X and Y:

X Y
molecular formula C4H6O C4H8O
boiling point / oC 81.4 79.6

(i) Explain why fractional distillation is NOT a suitable method to separate X from the mixture.
(1 mark)

[HKDSE_2019_q3(a)(ii)(c)]

3. (a) (ii) Organic compounds can be extracted by suitable solvents from their aqueous solutions. The
solvents should dissolve the organic compounds to be extracted without reacting with them. State
one other property these solvents should have. (1 mark)

3. (c) Chlorine reacted with ethylbenzene under sunlight to give a mixture of different
chlorinated compounds.

(i) Thin layer chromatography (TLC) was used to separate a small amount of the mixture.

(1) Explain briefly why chromatography can be used to separate a mixture.

(2) Based on the result in TLC, suggest a method to separate a large amount of the mixture.
(3 marks)