Ch.

44 Organic Reactions – Supplementary Exercise 3

1. <AL 1999 Paper I – 5a>
Under certain conditions, methane reacts with chlorine to give chloromethane as the major product.
i) State the conditions for the reaction.

ii) Outline the mechanism and name the mechanistic steps of the reaction.

iii) Is the reaction of methane with chlorine an appropriate method for the preparation of dichloromethane?
Explain. (5 marks)

2. <AL 1994 Paper I – 3b>

Give the major product from the reaction: CH3CH=CH2 + HBr

3. <AL 2009 Paper I – 4a>

Lysergic acid diethylamide (LSD) can be synthesized from lysergic acid in two steps as shown below:

What are reactants D and E?

4. <AL 2000 Paper I – 5b>

Give the reagents and conditions for the two steps of the conversion:

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5. <AL 2001 Paper I – 6b>
After some lessons in organic chemistry, a student remarked, ‘Alkanes are more stable than alkenes,
therefore alkanes do not react with chlorine but alkenes do.’
Do you agree with the student? Explain.
(3 marks)

6. <AL 1998 Paper I Q4>

Alcohol E has the structure CH3CH(OH)C2H5.
a) i) Draw a three-dimensional representation of E.

ii) What type of isomerism can be exhibited by E?

b) Draw the structures of three structural isomers of E, all of which are alcohols.

c) On treatment with H2SO4, E gives mainly two isomeric compounds, F and G, both of which have
the formula C4H8. On treatment with bromine, both F and G give a product H with formula
C4H8Br2.
i) Draw structures for F, G and H.

ii) What is the isomeric relationship between F and G?

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7. <AL 2001 Paper I Q8>
In an experiment to prepare propanal from propan-1-ol,
Na2Cr2O7/H3O+

CH3CH2CH2OH heat CH3CH2CHO

A side-product N (C6H12O2) was formed.

i) What is N? Suggest how N is formed.

ii) Suggest one method to separate propanal from a mixture of propanal and N.

8. <CE: 1994 B6b>

The following paragraph was taken from a student’s laboratory report:
‘A mixture of ethanol, ethanoic acid and several drops of concentrated sulphuric acid was heated under
reflux for some time. The resulting mixture was then cooled and poured into a beaker containing some
saturated sodium chloride solution.’
(i) Draw a labelled diagram of the experimental set-up used for heating the mixture under reflux.

(ii) Why is it necessary

(1) to use concentrated sulphuric acid in the above experiment?

(2) to heat the mixture under reflux?

(iii) What would be observed when the resulting mixture was poured into the saturated sodium chloride
solution?
(6 marks)

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9. <AL: 2002 II 6>
Both compounds K and L are natural fats that exist in human body.

(i) Draw structures of all products formed from the complete hydrolysis of K.

10. <AL: 1997 II Q5>

The following equation represents the acid hydrolysis of a dipeptide D to produce compounds E and F,
one of which is a chiral compound.

H3C O H3O+
E + F
H2NCHC NHCH2CO2H

(i) Name all functional groups in D.

(ii) Give one structure for E and one for F. Draw a suitable representation for the chiral product.

11. <CE: 1995 B7b>

The following flow diagram shows the conversion of a compound X to an acid Y.
oxidation
X Ethanol Y

X can rapidly decolourize a solution of bromine in 1,1,1-trichloroethane.

(i) What is X? Name the industrial process by which X is converted to ethanol.

(ii) Write a chemical equation for the reaction between X and bromine.

(iii) (1) Give the systematic name of Y.

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 (2) Draw a labelled diagram of the laboratory set-up for the conversion of ethanol to Y.

(iv) Ethanol can be detected in the breath of a drunken driver. Suggest ONE chemical test to show the
presence of ethanol in his breath and state the observable change produced by the test.
(9 marks)

12. <CE: 1998 B9a>

A student used the following set-up to prepare propanoic acid:

water out ←

← water in

a mixture ofpropan-1-ol and

pumice stones acidified potassium dichromate solution

heat

(i) Name apparatus X.

(ii) Explain why some pumice stones were added to the reaction mixture before heating.

(iii) Write the chemical equation for the reaction involved.

(iv) Suggest a method to obtain propanoic acid from the reaction mixture.

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 The student used the propanoic acid obtained to carry out the following experiment:

a mixture of propanoic acid,

methanol and a few drops of
concentrated sulphuric acid

sodium carbonate
solution

(v) Why is a water bath, instead of a naked flame, used for heating the test tube and its contents?

(vi) (1) State TWO observable changes when the contents of the test tube were added to the
sodium carbonate solution.

(2) Give the systematic name of the carbon compound formed in the experiment.
(8 marks)

13. <HKALE 2002>

In an attempt to prepare 1-methylcyclopentene, 1-methylcyclopentanol was allowed to react with
phosphoric acid. The reaction mixture was then subjected to simple distillation.
(a) Draw a labelled diagram to show the set-up of apparatus used in a simple distillation.

(b) Suggest a chemical test, giving the expected observation, to show the presence of an alkene in the
distillate.

(c) The distillate was shown to contain a small amount of unreacted 1-methylcyclopentanol. Suggest a
method to separate it from the desirable product.

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14. [HKDSE_2013_q15]
Consider the conversions of organic compounds shown below:

(a) Suggest a chemical test to distinguish between X and Y. (2 marks)

(b) Suggest what reagent R might be. (1 mark)

(c) The mixture Z contains two alkenes with the same structural formula. Draw the respective structures
of these two alkenes, and state their isomeric relationship. (2 marks)

(d) The alkenes in (c) can react with HCl to form an optically active chloroalkane. Write the structural
formula of this chloroalkane. (1 mark)

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