Chapter 42 Chapter exercise (p.
42)
A. Fill in the blanks (p.42)
1. (a) chloroform
(b) isopropyl alcohol
(c) formaldehyde
(d) acetone
(e) acetic acid
B. Practice questions (p.42)
2. (a) 2,3-dimethylpent-1-ene
(b) 1,5-dichloro-4-methylpent-2-ene
(c) 3-bromopropene
(d) 3,4-dibromo-4-chlorobut-1-ene
(e) 2-methylpentan-2-ol
(f) 4-chlorohex-4-en-2-ol
(g) 3,4-dimethylpentan-2-one
(h) 3-chlorohexanal
(i) 2,5-dimethylhex-4-enal
(j) 2-methylbutanedioic acid
(k) Ethyl 2-methylpropanoate
(l) But-3-en-1-amine
3.
(a) (i) (ii)
(b) (i) (ii)
(c) (i) (ii)
1
(d) (i) (ii)
(e) (i) (ii)
(f) (i) (ii)
(g) (i) (ii)
(h) (i) (ii)
(i) (i) (ii)
C. Multiple-choice questions (p.43)
4. A
5. D
6. C
7. A
D. Structured questions (p.44)
8. (a) Structure of hexan-1-ol:
Structure of hexane-1,6-diol:
1
2
(b) Hexane-1,6-diol has one more −OH group than hexan-1-ol. 1
Hence, hexane-1,6-diol molecules can form more extensive hydrogen bonding with
water molecules as compared with hexan-1-ol molecules. 1
9. (a) The molecular size of these primary amines increases from CH3NH2 to
CH3(CH2)5NH2. 1
The boiling point of primary amines increases with molecular size. 1
(b) CH3NH2 is very soluble in water. 1
This is because water solubility of primary amines decreases with the number of
carbon atoms in the alkyl group (or decreases as the length of the hydrocarbon chain
increases). 1
10. (a) Propan-2-ol 1
(b) Isopropyl alcohol can be used as a disinfectant for killing bacteria and other
potentially harmful micro-organisms. 1
(c) Propanone 1
(d) Acetone molecules can form hydrogen bonds with water molecules. 1
hydrogen bond
Chapter 42 Exam practice (p.46)
A. Multiple-choice questions (p.46)
1. C
2. D
3. B
(The author is responsible for the solutions and that (a) they have neither been provided nor
approved by AQA and (b) they may not necessarily constitute the only possible solutions.)
4. B
5. D
6. D
7. B
8. C
9. C
3
Each CH3CH2CONH2 molecule has two partially positively charged hydrogen atoms. Each
hydrogen atom can form a hydrogen bond with a lone pair of electrons on the oxygen atom of
another CH3CH2CONH2 molecule.
But for CH3CH2COOH, each of its molecules has only one partially positively charged hydrogen
atom. Hence, CH3CH2CONH2 molecules can form more extensive hydrogen bonding with each
other than CH3CH2COOH molecules.
As the intermolecular forces between CH3CH2CONH2 molecules are stronger than those between
CH3CH2COOH molecules, more energy is needed to overcome the intermolecular forces between
CH3CH2CONH2 molecules than those between CH3CH2COOH molecules during evaporation.
Hence, CH3CH2CONH2 is the least volatile.
10. A
CH3CH2OH and CH3CH2NH2 are both miscible with water. However, as the polarity of O−H
bond is higher than that of N−H bond, CH3CH2OH is more polar than CH3CH2NH2. Hence,
CH3CH2OH molecules interact more strongly with water molecules than CH3CH2NH2 molecules
do. Therefore, CH3CH2OH is the most soluble in water.
B. Structured questions (p.47)
11. (a) R, S and U 1
This is because they are all soluble in water. 1
(Note: molecules of ethanol, propan-1-ol and butan-1-ol can all form hydrogen
bonds with water molecules.)
(b) P and Q 1
This is because their boiling points are below 25C. 1
(c) The boiling point of carbon compounds of the same homologous series increases
with the length of hydrocarbon chain in their molecules (or the molecular size). 1
As the length of hydrocarbon chain (or the molecular size) increases, the van der
Waals’ forces between the molecules of carbon compounds become stronger. 1
(d) P: butane 1
Q: propane 1
R: butan-1-ol 1
S: propan-1-ol 1
T: pentane 1
U: ethanol 1
12. (a) CH3COOCH2CH2CH(CH3)2 1
(b) 3-methylbutan-1-ol 1
4
(c) Isoamyl acetate is a relatively non-polar compound. The intermolecular forces
between its molecules and the molecules of most non-polar organic solvents are of
comparable strength. 1
(Molecules of isoamyl acetate and molecules of most non-polar organic solvents
can be attracted by weak intermolecular forces.)
13. (a) Mole ratio of C atoms to H atoms to O atoms
40.0 6.7 53.3
= : : 1
12.0 1.0 16.0
= 3.33 : 6.7 : 3.33
=1:2:1
∴the empirical formula of X is CH2O. 1
Let the molecular formula of X be (CH2O)n, where n is an integer.
50 < (12.0 + 1.0 × 2 + 16.0) × n < 80
n=2
∴the molecular formula of X is C2H4O2. 1
(b)
and
(c) X has a low boiling point and a pleasant fruity smell. 2
14. (a) Methanal 1
(b)
1
(c) Formaldehyde molecules are held together by van der Waals’ forces, which are
weaker than the hydrogen bonds existing predominantly between methanol
molecules. 1
Thus, a smaller amount of energy is needed to overcome the intermolecular forces
between formaldehyde molecules and separate them during boiling. 1