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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
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)
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
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
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
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
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
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%
a
b
50%
90%
A18.
a
b
Q19.
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.
OH
CH3CH2Cl(g)
CH3CH2OH(aq)
Cr2 O7 ,H
CH3CH2OH(aq)
CH3COOH(aq)
Q22.
substitution
addition
substitution
oxidation
Q23.
A23.
a
10
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
II
III
IV
a
b
c
d
e
12
d
e
Q27.
A27.
a
b
c
CH3CH2COOCH3(l) + H2O(l)
CH3COO(CH2)4CH3(l) + H2O(l)
HCOOCH(CH3)2(l) + H2O(l)
Q28.
a
b
c
A28.
a
b
c
2SO4
CH3COOH(l) + CH3(CH2)2OH(l) H
CH3COO(CH2)2CH3(l) + H2O(l)
condensation and esterification
catalyst
13
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.
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
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.
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
15
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