HKDSE CHEMISTRY — A Modern View (Second Edition)

Part XI Chemistry of carbon compounds

Chemistry: Chapter 42 Introduction to selected homologous series

Structured questions

Sections 42.142.4
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Consider the following compounds:

(a) Draw a labelled diagram to show the hydrogen bond formation between
propanoic acid molecules. (2 marks)

*(b) Compare the boiling points of the two compounds above. Explain your answer.
(4 marks)

(c) Propanoic acid can react with propan-1-ol to form an ester. Draw the structure of
the ester. (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

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(a)

hydrogen bond

Correct orientation of molecules 1

Correct labels of hydrogen bond(s) 1
(b) - Propanoic acid has a higher boiling point than propan-1-ol. 1
- In the carboxyl group of propanoic acid, both C=O and OH groups
can participate in hydrogen bond formation. 1
- Hence, more extensive hydrogen bonds form between propanoic
acid molecules than propan-1-ol molecules. 1
- Communication mark 1
(c)

1
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The structural formula of glycerol is shown below.

(a) Give the systematic name of glycerol. (1 mark)

(b) State and explain whether glycerol is miscible with water. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

(c) (i) Write the condensed structural formula of propan-1-ol. (1 mark)

(ii) Compare the boiling points of glycerol and propan-1-ol. Explain briefly.
(3 marks)

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(a) Propane-1,2,3-triol 1
(b) Glycerol is miscible with water 1
as the hydroxyl groups enable glycerol molecules to form hydrogen
bonds with water molecules. 1
(c) (i) CH3CH2CH2OH 1
(ii) Glycerol has a higher boiling point than propan-1-ol. 1
Each propan-1-ol molecule forms one hydrogen bond on average
while each glycerol molecule forms three hydrogen bonds on
average. 1
More energy is needed to overcome the extensive hydrogen bonds
between the glycerol molecules during boiling. 1
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*Consider the following compounds:
Butane, butan-1-ol, butanoic acid, methylpropane
Arrange the above compounds in ascending order of boiling points. Explain your
answer. (6 marks)

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Part XI Chemistry of carbon compounds

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- Methylpropane < butane < butan-1-ol < butanoic acid 1
- Butanoic acid molecules and butan-1-ol molecules are held together by
hydrogen bonds as well as van der Waals’ forces. 1
- However, for butanoic acid molecules, both C=O group and OH group
can participate in hydrogen bond formation. More energy is needed to
overcome the extensive hydrogen bonds among butanoic acid molecules
than those among butan-1-ol molecules. 1
- Butane molecules and methylpropane molecules are held together by van
der Waals’ forces only. 1
- Methylpropane is a branched-chain alkane in which the spherical
molecules have a smaller area of contact than rod-shaped butane
molecules. The van der Waals’ forces between methylpropane molecules
are weaker. 1
- Communication mark 1
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A saturated carboxylic acid has the relative molecular mass of 88.0.

(a) Give the general formula of carboxylic acids. (1 mark)

(b) Deduce the molecular formula of the carboxylic acid.

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(c) Name and draw all the possible structures of the carboxylic acid. (4 marks)

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(a) CnH2n+1COOH 1
(b) (n + 1) × 12.0 + (2n + 2) × 1.0 + 2 × 16.0 = 88.0
14.0n + 46.0 = 88.0
n=3 1
∴ the molecular formula of the carboxylic acid is C3H7COOH. 1
(c)

Butanoic acid 1

2-methylpropanoic acid 1
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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

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The table below shows some information for three carbon compounds.

Butanal Butanone Butan-1-ol

Structural formula CH3(CH2)2CHO CH3CH2COCH3 CH3(CH2)3OH
Molecular mass 72.0 72.0 74.0
Boiling point (C) 74.8 79.6 118

(a) What type of intermolecular forces is present in all three compounds? (1 mark)

(b) Explain why butan-1-ol has a higher boiling point than butanal and butanone.
(2 marks)

(c) With the aid of a diagram, explain which of the above compounds is the most
soluble in water. (3 marks)

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(a) Van der Waals’ forces 1
(b) Butan-1-ol molecules are held together by hydrogen bonds and van der
Waals’ forces while butanal molecules and butanone molecules are held
together by van der Waals’ forces only. 1
The intermolecular forces between butan-1-ol molecules are stronger than

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

those between butanal molecules and butanone molecules. 1

(c) Butan-1-ol is the most soluble in water as the hydroxyl group (OH)
contains both O atom and H atom which can form hydrogen bonds with
water molecules. 1

hydrogen bond

Correct orientation of molecules 1

Correct labels of hydrogen bond(s) 1
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Consider the following compounds:

A B C
(a) Name the homologous series that each of them belongs to. (3 marks)

(b) Which of the above compounds can form hydrogen bonds among its molecules?
(1 mark)

*(c) Arrange the compounds in descending order of boiling points. Explain your
answer. (4 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

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(a) A belongs to aldehydes. 1
B belongs to ketones. 1
C belongs to carboxylic acids. 1
(b) C 1
(c) - C>B>A 1
- The molecules of C are held together by hydrogen bonds and van der
Waals’ forces while the molecules of A and B are held together by
van der Waals’ forces only. Hence, C has the highest boiling point. 1
- Since the molecules of B have a larger molecular size than A, the
van der Waals’ forces among the molecules of B are stronger. 1
- Communication mark 1
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Vanillin is a key ingredient in vanilla ice-cream. The structure of vanillin is shown
below:

(a) Write the skeletal formula of vanillin. (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

(b) Name TWO functional groups of vanillin. (2 marks)

(c) Explain why vanillin is slightly soluble in water. (2 marks)

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(a)

(b) Any TWO:

Hydroxyl group / carbonyl group / benzene ring / ether group 2
(c) The hydroxyl group and carbonyl group enable the molecules to form
hydrogen bonds with water molecules, 1
but the non-polar benzene ring hinders the formation of hydrogen bonds
between its molecules and water molecules. 1
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The aroma of raspberry is primarily due to the presence of raspberry ketone. In
general, only about 4 mg of raspberry ketone can be extracted from 1 kg of raspberry.

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

raspberry raspberry ketone

(a) Estimate the mass of raspberry needed to extract one mole of raspberry ketone.
(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(b) Besides the carbonyl group, state ONE other functional group present in
raspberry ketone. (1 mark)

(c) State the strongest type of intermolecular forces between raspberry ketone
molecules. (1 mark)

(d) State and explain whether raspberry ketone is soluble in water. (2 marks)

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(a) Molar mass of raspberry ketone
= (12.0 × 10 + 1.0 × 12 + 16.0 × 2) g mol1 = 164.0 g mol1 1
Mass of raspberry needed for extracting one mole of raspberry ketone

= × 1000 g = 4.1 × 107 g 1

(b) Hydroxyl group / benzene ring 1

(c) Hydrogen bonding 1
(d) Raspberry ketone is insoluble in water. 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

Although raspberry ketone has a hydroxyl group, the long carbon chain
hinders the formation of hydrogen bonds between its molecules and water
molecules. 1
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Ethyl butanoate can be used to manufacture hand creams. It has a pineapple smell.

(a) Which homologous series does ethyl butanoate belong to? (1 mark)

(b) Write the structural formula for ethyl butanoate. (1 mark)

(c) Explain whether ethyl butanoate is an acid derivative. (1 mark)

(d) Consider the following information:

Hexanoic acid Ethyl butanoate

Boiling point 205C 121C
Relative molecular mass 116 116

Explain briefly why hexanoic acid has a much higher boiling point than ethyl
butanoate. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

(a) Ester 1
(b)

(c) It is an acid derivative as it is made by the reaction of butanoic acid. 1

(d) Hexanoic acid molecules are held together by hydrogen bonds and van
der Waals’ forces while ethyl butanoate molecules are held together by
van der Waals’ forces only. 1
More energy is needed to overcome the hydrogen bonds between
hexanoic acid molecules during boiling process. 1
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Consider the following compounds:
hexan-3-ol, hexanal, hexan-2-amine

(a) Which of the above compounds are soluble in water? Explain briefly. (2 marks)

*(b) Arrange the above compounds in increasing order of boiling points. Explain your
answer. (5 marks)

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(a) They are all soluble in water 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

because their molecules can form hydrogen bonds with water molecules. 1
(b) - Hexanal < hexan-2-amine < hexan-3-ol 1
- Hexan-2-amine molecules and hexan-3-ol molecules are held
together by hydrogen bonds and van der Waals’ forces while hexanal
molecules are held together by van der Waals’ forces only. 1
- Hence, the boiling points of hexan-2-amine and hexan-3-ol are
higher than that of hexanal. 1
- Nitrogen is less electronegative than oxygen. The hydrogen bonds
between hexan-2-amine molecules are weaker than those between
hexan-3-ol molecules. 1
- Communication mark 1
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After an animal dies, bacteria will break down proteins of the body and some amines
are produced. For example, NH2(CH2)4NH2 and NH2(CH2)5NH2 are found in decaying
animal flesh. These amines are partly responsible for the unpleasant smell of dead
bodies.

(a) Give the systematic names of NH2(CH2)4NH2 and NH2(CH2)5NH2. (2 marks)

(b) Compare the boiling points of NH2(CH2)4NH2 and NH2(CH2)5NH2. Explain your
answer. (2 marks)

(c) Draw a labelled diagram to show the hydrogen bond formation between
NH2(CH2)4NH2 molecules. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XI Chemistry of carbon compounds

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(a) NH2(CH2)4NH2: Butane-1,4-diamine 1
NH2(CH2)5NH2: Pentane-1,5-diamine 1
(b) NH2(CH2)4NH2 has a lower boiling point than NH2(CH2)5NH2. 1
NH2(CH2)4NH2 has a smaller molecular size than NH2(CH2)5NH2. The
van der Waals’ forces between NH2(CH2)4NH2 molecules are weaker. 1
(c)

hydrogen bond

Correct orientation of molecules 1

Correct labels of hydrogen bond(s) 1
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