12 Basic concepts in organic chemistry Answers to Practice questions

Pages 199–201 Practice questions

1 B [1]
2 A [1]
3 C [1]
4 C [1]
5 C [1]
6 C [1]
7 A [1]
8 C [1]
9 A [1]
10 A [1]
11 The functional group can usually be identified from the last few letters of the name, the
exception to this is the halogenoalkane:
a) dodecane – alkane [1]
b) pentene – alkene [1]
c) propane –alkane [1]
d) propan-2-ol – alcohol [1]
e) 2-bromobutane – halogenoalkane [1]
f) cyclobutane – alkane [1]
12 a) C2H5OH is followed by C3H7OH [1]
b) C3H6 is followed by C4H8 [1]
c) CH3I is followed by C2H5I [1]
d) C7H16 is followed by C8H18 [1]
(Each homologous series has the same general formula and each differs from the next
member in the series by CH2.)
13 a)

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12 Basic concepts in organic chemistry Answers to Practice questions

b)

c)

The OH group should be fully displayed but it is usually acceptable to simply write it as OH.
d)

A displayed formula should show every bond – but it is usually okay to show the methyl group
as a CH3 rather than drawing out the methyl side chain.
e)

The really important feature of this molecule is the alkene C=C double bond that must be fully
displayed; the methyl group can usually be written as CH3. [5 marks – both displayed and
structural
formulae needed for each mark]

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12 Basic concepts in organic chemistry Answers to Practice questions

14 a)

[1]
b)

[1]
c)

[1]
d)

[1]
15 a) i) Compound A:
C:H:O
37.5 12.5 50
: :
12 1 16

3.125 : 12.5 : 3.125

3.125 12.5 3.125
: :
3.125 3.125 3.125

1:4:1
Empirical formula = CH4O [2]
ii) Empirical formula of compound B is C3H7Br. [2]
iii) Empirical formula of compound C is C2H5O. [2]
b) Compound B can be either 1-bromopropane or 2-brompropane. [2]

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12 Basic concepts in organic chemistry Answers to Practice questions

c) Compound C has the empirical formula C2H5O and relative molecular mass = 90.
molecular mass 90
The number of empirical units needed to make up the molecular mass is = =2
empirical mass 45

Hence the molecular formula is made of two empirical units (C2H5O)2 or C4H10O2. [2]
There are lots of possible isomers. [6]

molecular mass of the desired product

16 Atom economy = × 100
sum of the molecular masses of all products

Molecular mass of desired product = 136.9 g mol−1

Molecular mass of all the products = 136.9 + 120.1 + 18.0 = 275.0 g mol–1
136.9
Atom economy = ( ) × 100 = 49.8%. [2]
275

17 a) CH3CH2CH2CH3; butane [1]

b) CH3CHBrCH3; 2-bromopropane [1]
The 2 is not necessary but students often find it easier and logical to include it. Either would
be acceptable in an exam.
c) CH3CHCHCH3; but-2-ene [1]
d) (CH3)4C; 2,2-dimethylpropane [1]
Difficult to work out and students should be advised to draw out the displayed formula.
e) CH3CH2CH(CH3)CH2CH3; 3-methylpentane [1]
This time the number is essential – methyl pentane is ambiguous and would not get a mark in
the exam.
18 a)

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12 Basic concepts in organic chemistry Answers to Practice questions

[1]
b)

[1]

c)

[1]
d)

[1]
e)

[1]
Propan-1-ol is much more difficult as students often draw a skeletal structure showing three
carbons and simple add the OH to the end carbon which immediately converts the structure
to ethanol rather than propan-1-ol]
19

[4]
10
20 a) Relative molecular mass of C6H11OH is 100 therefore the number of mol used is = 0.1 mol
100

and hence the number of mol of C6H10 that could have been made is also 0.1 mol.
0.1 mol of C6H10 has a mass of 8.20 g. The percentage yield is therefore 40%. [2]

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12 Basic concepts in organic chemistry Answers to Practice questions

molecular mass of the desired product

b) Atom economy = × 100
sum of the molecular masses of all products

molecular mass of C6 H10

= × 100
sum of the molecular mass of C6 H10 +molecular mass of H2 O
80
= × 100 = 82% [2]
100

21 a) i) E [1]
ii) C6H14 [1]
iii) C2H5 [1]
b) i) C, D and F [1]
ii) Compounds/molecules with the same molecular formula but a different
structure/structural formula. [1]
−1
c) Molar mass of compound F is C5H12 = 60.0 + 12.0 =72.0 g mol [1]
60.0
Mass of C in compound F = 60.0; hence % C = ( ) x 100 = 83.3% (83%) [1]
72.0

22 a) (CH3)2C(OH)CH3 + HCl → (CH3)2CClCH3 + H2O [1 mark for correct organic formula, 1 mark for
balanced equation]
b) The molar ratio (CH3)2C(OH)CH3 : (CH3)2CClCH3 is 1 : 1 [1]
4.0
4.0 g of (CH3)2CClCH3 is = 0.0432 mol which represents a 40% yield. [1]
92.5
100
Hence the maximum yield that could have been obtained is ( ) × 0.0432 = 0.108 mol. [1]
40

0.108 mol of C4H9OH has a mass of 0.108 × 74.0 = 8.0 g. [1]

88.24
23 Ratio C : H is = 7.35 mol C : 11.76 mol H
12

Which gives 1 mol C : 1.6 mol H (this MUST NOT be rounded). [1]
Multiply by 5 to give 5 mol C : 8 mol H, hence empirical formula is C5H8. [1]
Empirical mass = 68, hence molecular formula is C5H8. [1]
Possible cycloalkenes include:
[1 mark for each correctly identified]

24 a) i) C : H : Br
12.9 1.1 86
: :
12 1 79.9

1.08 : 1.1 : 1.08 [1]

1:1:1
Empirical formula = CHBr [1]
ii) The number of empirical units needed to make up the molecular mass is

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12 Basic concepts in organic chemistry Answers to Practice questions

molecular mass 278.7

= =3
emperical mass 92.9

Hence the molecular formula is made of three empirical units (CHBr)3 or C3H3Br3. [1]
b) i) [12_A_39] [2]
ii) [12_A_40] [2]
(If these exist they are likely to be very unstable, however credit would be given in an
exam.)
iii) 1,2,3-tribromopropene [1]
2.787
c) i) Amount of compound A = = 0.01 mol
278.7
0.843
Amount of 1,1,2-tribromopropane = = 0.003
280.7
0.03
% yield = ( ) × 100 = 30% [2]
0.01

ii) 1,1,2-Tribromopropene C3H3Br3 (credit would be given for either the E- or the Z-isomer)
[2]
iii) 100% [1]

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