Chem ch10

Worked solutions to student book questions
Chapter 10 Organic reactions: pathways to new

products
Q1.
Write balanced equations to represent the formation of all possible products of the
reactions of chlorine with methane.
A1.
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)
CH3Cl(g) + Cl2(g) CH2Cl2(g) + HCl(g)
CH2Cl2(g) + Cl2(g) CHCl3(g) + HCl(g)
CHCl3(g) + Cl2(g) CCl4(g) + HCl(g)
Q2.
Draw the structural formulas and name all the possible products that can be formed by
the reaction of chlorine with ethane. Which substances are isomers?
A2.
chloroethane: 1,1-dichloroethane; 1,2-dichloroethane; 1,1,1-trichloroethane

1,1,2-trichloroethane: 1,1,1,2-tetrachloroethane; 1,1,2,2-tetrachloroethane
1,1,1,2,2-pentachloroethane: hexachloroethane
Isomers are 1,1-dichloroethane and 1,2-dichloroethane
1,1,1-trichloroethane and 1,1,2-trichloroethane
1,1,1,2-tetrachloroethane and 1,1,2,2-tetrachloroethane
Heinemann Chemistry 2 4th edition Enhanced

Copyright Pearson Australia 2010 (a division of Pearson Australia Group Pty Ltd)

products
Q3.
Name the products formed when ethene reacts with:
a hydrogen chloride
b chlorine
c water
d hydrogen
A3.
a
b
c
d
chloroethane
1,2-dichloroethane
ethanol
ethane
Q4.
Use structural formulas to write equations and name the products for the reactions of:
a but-1-ene with chlorine
b but-2-ene with hydrogen bromide
A4.
a


products
Q5.
Polyethenol is used to make soluble hospital laundry bags. The structure of the
monomer ethenol is shown in Figure 10.9. Draw the structure of a section of the
polymer.
Figure 10.9
Structure of ethenol.
A5.
Q6.
Draw molecular structures and refer to the electronegativities given in the periodic
table at the end of this book to work out whether each of the following substances has
a dipole or is non-polar.
a CH3F
b CH3CCl3
c CCl3CH2CCl3
A6.
a
b
c
polar
polar
non-polar
Q7.
Write unbalanced equations for the production of:
a methanol from chloromethane
b chloromethane from methane
c propan-1-ol from 1-chloropropane
A7.
a
b
OH
CH3Cl(g)
CH3OH(aq)
Cl2
CH4(g)
CH3Cl(g)
UV light
OH
CH3CH2CH2Cl(l)
CH3CH2CH2OH(l)


products
Q8.
Write a sequence of reactions that shows the production of:
a ethanoic acid from ethane
b ethanoic acid from ethene.
A8.
a
b
Cr2 O7
Cl 2
OH
CH3CH3(g)
CH3CH2Cl(g)
CH3CH2OH(aq)
heat or UV light
H+
CH3COOH(aq)
Cr2 O7 2
H2O
CH3COOH(aq)
CH2CH2(g)
CH3CH2OH(g)
H3 PO 4 catalyst
H+
Q9.
Label each step in Question 8 to show whether it is an addition, substitution or
oxidation reaction.
A9.
a
b
substitution, substitution, oxidation

addition, oxidation
Q10.
Write balanced equations for the reaction between ethanoic acid and:
a sodium hydroxide solution
b magnesium metal
c sodium carbonate solution.
A10.
a
b
c
CH3COOH(aq) + NaOH(aq) CH3COONa(aq) + H2O(l)

2CH3COOH(aq) + Mg(s) (CH3COO)2Mg(aq) + H2O(l)
2CH3COOH(aq) + Na2CO3(aq) 2CH3COONa(aq) + CO2(g) + H2O(l)


products
E1.
A condensation polymer used in medical sutures is made from glycolic acid
monomer. The semi-structural formula of glycolic acid is HOCH2COOH.
a What is meant by the term condensation polymer?
b Name the functional groups present in glycolic acid.
c Write an equation to represent the formation of a section of the polymer.
d Draw the structural formula for a section of the polymer and circle the ester bond.
AE1.
a
b
c, d
When condensation polymers are formed, small molecules such as water are
eliminated when the monomer molecules combine.
hydroxyl,OH and carboxyl, COOH functional groups
Q11.
Draw the structural formulas of the following esters and name them.
a CH3COOCH3
b CH3COOCH2CH3
c CH3CH2COOCH2CH3
A11.
a


products
c
Q12.
Write equations that describe the formation of an ester that smells like:
a pineapple (ethyl butanoate)
b rum (ethyl methanoate).
A12.
a
b
2SO4
CH3CH2CH2COOH(l) + CH3CH2OH(l) H
CH3CH2CH2COOCH2CH3(l) + H2O(l)
H2SO4
HCOOH(l) + CH3CH2OH(l) HCOOCH2CH3(l) + H2O(l)
Q13.
Devise reaction pathways for the following reactions:
a ethylamine from ethene
b butan-1-ol from butane
c pentanoic acid from 1-chloropentane
A13.
a
NH 3
H2O
Ethene
ethanol
ethylamine
Cl2
OH
1-chlorobutane
Butane
butan-1-ol
Cr2 O7 ,H
OH
1-Chloropentane
pentanoic acid
1-pentanol
Q14.
Name these esters and provide the systematic name of the alkanols and carboxylic
acids used to form them.
a CH3CH2CH2CH2COOCH3
b CH3CH2COOCH2CH2CH2CH2CH2CH3
A14.
a
b
methyl pentanoate, from methanol and pentanoic acid

hexyl propanoate, from hexanol and propanoic acid
Q15.
Propose the shortest reaction pathway that will synthesise the following:
a methanoic acid from methane
b ethanol from ethene
c propyl methanoate from propane and methane


products
A15.
a
b
c
i
Cr2 O7 ,H
Cl2 ,UV light
OH
methane
chloromethane
methanoic
methanol
acid
H2O
ethene
ethanol
This synthesis can be carried out in three stages: (i) synthesis of propan-1-ol,
(ii) synthesis of methanoic acid and (iii) synthesis of 1-propyl methanoate
Cl2
OH
propene
1-chloropropane
and
propan-1-ol
Cr2 O7 ,H
Cl2
OH
chloromethane
methanoic acid
methane
methanol
then
H+
iii propan-1-ol + methanoic acid
1-propyl methanoate + water
ii
Q16.
Describe a reaction pathway to synthesise 1-butyl ethanoate using the appropriate
alkanes or alkenes as starting materials.
A16.
This synthesis is carried out in three parts: (i). synthesis of 1-butanol, (ii) synthesis of
ethanoic acid and (iii) synthesis of 1-butyl ethanoate.
Cl2
OH
i butane
1-chlorobutane
butan-1-ol
2
Cr2 O7 ,H
H2O
ii ethene
ethanoic acid
ethanol
iii ethanoic acid + butan-1-ol 1-butyl ethanoate + water
Q17.
Calculate the percentage yield if 5.0 g of ethanol is oxidised to produce 4.8 g of
ethanoic acid.
A17.
2
Cr2 O7 ,H
CH3CH2OH
CH3COOH
Theoretical yield (100% conversion of ethanol)
n(CH3COOH) = n(CH3CH2OH)
5
mol
=
46
5
60 g = 5.2 g
m(CH3COOH) =
46
actual mass product obtained
% yield
=
100%
theoretical mass product
4.8
=
100
5.2
= 92%


products
Q18.
Compound D can be synthesised using a reaction pathway that involves a number of

intermediate steps. The yield for each step is shown.
A B C D
70%
a
b
50%
90%
Determine the overall yield for the preparation of compound D from

compound A.
How would the overall yield be affected if the yield for B C was only 10%?
A18.
a
b
yield = 0.7 0.5 0.9 = 0.32; Yield = 32%

yield = 0.7 0.1 0.9 = 0.063; Yield = 6.3%
Q19.
Briefly describe the principles of fractional distillation.

A19.
In fractional distillation, the components of a mixture of volatile liquids are separated

by what can be considered to be a succession of simple distillations. The temperature
gradient in the fractionating column allows this to occur. Fractional distillation relies
on the phenomena that the concentration of the low boiling point component in the
vapour over a mixture of volatile liquids is higher than in the liquid.
As the mixture of liquids is heated in the distillation flask, the vapours that move up
the fractionating column contain a higher concentration of the more volatile liquid.
The vapours eventually reach a height in the fractionating column where the
temperature is low enough for condensation to occur. As the condensed liquid moves
back down the column it is reheated by vapours rising from the distillation flask.
Some of this condensed liquid evaporates and the resulting vapour has an even higher
concentration of the low boiling point substance. This process of evaporation and
condensation is repeated many times. The concentration of the more volatile
substance increases in each evaporationcondensation cycle. Once the vapour reaches
the top of the fractionating column it will ideally consist of only the more volatile
component. When the relatively pure component reaches the top of the fractionating
column, the temperature remains relatively stable. The material that condenses over a
small temperature range near the boiling point is collected once it has passed through
the condenser.
Q20.
Methane undergoes a series substitution reactions with bromine to form a number of

compounds with the following boiling points: bromomethane (3.6C),
dibromomethane (97C), tribromomethane (150C) and tetrabromomethane (190C).
Describe how you would obtain pure samples of each compound from the mixture.


products
A20.
The mixture of volatile liquids can be separated by fractional distillation. The mixture
is placed in the distillation flask and heated. The most volatile compound
(bromomethane) is the first to reach the top of the fractionating column and condense.
The fraction condensing in a narrow range of temperatures around the boiling point
3.6C is collected. Because this temperature is below that of room temperature, the
receiving flask should be surrounded by ice to condense the liquid bromomethane.
The next fraction to be collected at around 97C will contain dibromomethane.
Tribromomethane will be found in the fraction collected at 150C.
Tetrabromomethane will found in the fraction collected at 190C.
Chapter review
Q21.
Write unbalanced equations for the production of:

a chloroethane from ethane
b ethanol from ethene
c ethanol from chloroethane
d ethanoic acid from ethanol.
A21.
a
b
Cl2 ,UV light

CH3CH3(g)
CH3CH2Cl(g)
H2 O
CH2CH2(g)
CH3CH2OH(g)
H3 PO 4 catalyst
OH
CH3CH2Cl(g)
CH3CH2OH(aq)
Cr2 O7 ,H
CH3CH2OH(aq)
CH3COOH(aq)
Q22.
Classify the reactions in your answers to Question 21 as addition or substitution.

A22.
a
b
c
d
substitution
addition
substitution
oxidation
Q23.
Write the structural formulas of the products of the following reactions:

a


products
b
A23.
a

10

products
Q24.
Write an unbalanced chemical equation for the reaction between:

a butane and chlorine
b 1-chlorobutane and sodium hydroxide solution
c butan-1-ol and acidified potassium dichromate solution
d propan-1-ol and acidified potassium permanganate solution
e ethane and oxygen.
A24.
a
Cl2 ,UV light

CH3CH2CH2CH3(g)
CH3CH2CH2CH2Cl(l)
OH
CH3CH2CH2CH2Cl(l)
CH3CH2CH2CH2OH(aq)
Cr2 O7 ,H
CH3CH2CH2CH2OH(aq)
CH3CH2CH2COOH(aq)
MnO 4 ,H
CH3CH2CH2OH(aq)
CH3CH2COOH(aq)
2C2H6(g) + 7O2(g) 4CO2(g) + 6H2O(g)
Q25.
Write chemical equations in the form of a flow diagram (similar to Figure 10.31) to
describe the preparation of propanoic acid from an:
a alkane
b alkene.
A25.
a

11

products
Q26.
Consider the following compounds:

I
II
III
IV
a
b
c
d
e
Write the names of each of these compounds.

Which of these compounds is a member of the alkane homologous series?
Give one important difference in chemical behaviour between compounds I
and V.
What important chemical is manufactured from compound II?
Which of these compounds dissolves in water to form an acidic solution?

12

products
A26.
a
b
c
d
e
I methane, II chloroethane, III propane, IV ethanoic acid, V propene

I, III
Compound V will decolourise bromine almost immediately, whereas compound I
will not. In general, compound I participates in substitution reactions (e.g.
chlorination by chlorine gas to form chloromethane) whereas compound V
participates in addition reactions (e.g. addition of HCl across the double bond to
form chloropropane).
ethanol
IV
Q27.
Complete the following reactions:

a
A27.
a
b
c
CH3CH2COOCH3(l) + H2O(l)
CH3COO(CH2)4CH3(l) + H2O(l)
HCOOCH(CH3)2(l) + H2O(l)
Q28.
a
b
c
Write a chemical equation to describe the preparation of propyl ethanoate from an

alkanol and a carboxylic acid.
What name is given to this type of reaction?
Sulfuric acid would be present in the reaction mixture. Why?
A28.
a
b
c
2SO4
CH3COOH(l) + CH3(CH2)2OH(l) H
CH3COO(CH2)2CH3(l) + H2O(l)
condensation and esterification
catalyst

13

products
Q29.
Write equations to show the production of:

a methyl ethanoate
b ethyl propanoate.
A29.
a
b
2SO4
CH3COOH(l) + CH3OH(l) H
CH3COOCH3(l) + H2O(l)
2SO4
CH3CH2COOH(l) + CH3CH2OH(l) H
CH3CH2COOCH2CH3(l) +
H2O(l)
Q30.
Write the formula of the alkanol and carboxylic acid used to make the following
esters:
a CH3COOCH2CH3
b CH3CH2COOCH2CH3
A30.
a
b
CH3CH2OH, CH3COOH
CH3CH2OH, CH3CH2COOH
Q31.
In an experiment, the reaction of chlorine with ethane resulted in a mixture containing

a number of products with the following boiling points: chloroethane (12C),
1,1-dichloroethane (57C), 1,2-dichloroethane (84C), and 1,1,2-trichloroethane
(97C). Describe how you could obtain a pure sample of 1,2-dichloroethane from this
mixture.
A31.
The mixture of volatile liquids can be separated by fractional distillation. The mixture
is placed in the distillation flask and heated. The components in the mixture are
separated in order of their boiling points with the most volatile component,
chloroethane, being the first fraction to condense. This is followed by the fraction
containing1,1-dichloroethane. The fraction condensing in a narrow range of
temperatures around the boiling point of 1,2-dichlorethane, 84C, is then collected in
a new receiving flask.
Q32.
Complete the missing structural formulas and name the compounds A, B and C.

14

products
A32.
A
B
C
NaOH(aq)
Q33.
Give the semi-structural formulas for substances P and Q and the systematic names
for substances R and S in the following equation:
A33.
Formula P: CH3OH
Formula Q: H2O
Substance R: propanoic acid
Substance S: methyl propanoate
Q34.
Write a reaction pathway for the synthesis of:

a ethyl propanoate from ethene and propene
b ethyl ethanoate from an alkene.
A34.
a
Preparation of ethanol
H 2 O(g)
ethene
ethanol
Synthesis of propanoic acid
H 2 (g)
Cl2 , UV light
OH
propene
propane
1-chloropropane
propan-1-ol
2
Cr2 O7 ,H
propanoic acid
Preparation of ethyl propanoate

ethanol + propanoic acid ethyl propanol + water
Preparation of ethanol
H 2 O(g)
ethene
ethanol
Preparation of ethanoic acid
Cr2 O7 2 ,H +
H 2 O(g)
ethanoic acid
ethene
ethanol
ethanol + ethanoic acid ethyl ethanoate + water

15

products
Q35.
Fractional distillation is an important laboratory technique.

a What is fractional distillation used for?
b Fractional distillation has been described as a series of simple distillations.
Explain.
A35.
Fractional distillation is used to separate liquids that have different boiling points.
It is commonly used in the laboratory to separate volatile liquids from a reaction
mixture. Industrial applications of fractional distillation include:
Separation of the fractions from crude oil.
Production of oxygen and nitrogen by the fractional distillation of liquid air.
Extraction of ethanol from water in the fermentation of sugar.
b The mixture of liquids is heated in the distillation flask. The vapours that move
up the fractionating column contain a higher concentration of the more volatile
liquid. The vapours eventually reach a height in the fractionating column where
the temperature is low enough for condensation to occur. As the condensed liquid
moves back down the column it is reheated by vapours rising from the distillation
flask. Some of this condensed liquid evaporates and the resulting vapour has an
even higher concentration of the low boiling point substance. This process of
evaporation and condensation is repeated many times. The concentration of the
more volatile substance increases in each evaporationcondensation cycle. At the
same time the concentration of the less volatile (higher boiling point) substance in
the distillation flask will increase. Once the vapour reaches the top of the
fractionating column it will ideally consist of only the most volatile component.
a

16

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Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

chloroethane: 1,1-dichloroethane; 1,2-dichloroethane; 1,1,1-trichloroethane

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

substitution, substitution, oxidation

CH3COOH(aq) + NaOH(aq) CH3COONa(aq) + H2O(l)

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

methyl pentanoate, from methanol and pentanoic acid

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Compound D can be synthesised using a reaction pathway that involves a number of

Determine the overall yield for the preparation of compound D from

yield = 0.7 0.5 0.9 = 0.32; Yield = 32%

Briefly describe the principles of fractional distillation.

In fractional distillation, the components of a mixture of volatile liquids are separated

Methane undergoes a series substitution reactions with bromine to form a number of

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Write unbalanced equations for the production of:

Cl2 ,UV light

Classify the reactions in your answers to Question 21 as addition or substitution.

Write the structural formulas of the products of the following reactions:

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Write an unbalanced chemical equation for the reaction between:

Cl2 ,UV light

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Consider the following compounds:

Write the names of each of these compounds.

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

I methane, II chloroethane, III propane, IV ethanoic acid, V propene

Complete the following reactions:

Write a chemical equation to describe the preparation of propyl ethanoate from an

Heinemann Chemistry 2 4th edition Enhanced

Worked solutions to student book questions

Chapter 10 Organic reactions: pathways to new

Write equations to show the production of:

In an experiment, the reaction of chlorine with ethane resulted in a mixture containing