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HOMEWORK GUIDE

CHAPTER 22: Alkanols

Summary

A homologous series

• The alkanols are a homologous series with the general formula CnH2n+1OH. The names
always end in -ol. All have the hydroxyl group –OH, which gives the alkanols similar
chemical properties.
Note: The hydroxyl group --OH is covalent, and differs from OH-, which is the hydroxide
ion.
• The first two alkanols are methanol CH3OH and ethanol C2H5OH or CH3CH2OH.
Structural formulae of ethanol

• Ethanol is the most important alcohol.

Preparation of ethanol

• By fermentation of sugars found in plants, e.g. grapes, barley, rice. Fermentation is the
conversion of large molecules (e.g.. starch, sugars) to smaller molecules (e.g., ethanol) by
micro-organisms (e.g. yeast). For example, the fermentation of a sugar (glucose):
enzymes in
C6H12O6(aq) -------------------> 2C2H5OH(aq) + 2CO2(g)
yeast
glucose ethanol carbon dioxide
O
The process works best at about 37 C; higher temperatures kill the yeast. The maximum
concentration of ethanol is about 18%. This is because the yeast dies at higher
concentration and fermentation stops. The concentration can be increased by fractional
distillation.
• By the catalytic hydration of ethene
Ethanol and steam are passed over a catalyst of phosphoric acid at 300OC and high
pressure.
phosphoric acid
C2H4(g) + H2O(g) ------------------------>
O C2H5OH(g)
300 C

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Uses of lower alkanols

• As solvents: E.g. In perfumes and cosmetics to dissolve fragrant oils.


Methylated spirit is a mixture of methanol and ethanol.
• As fuels: E.g. Ethanol in spirit burners, as a fuel for cars in some countries (e.g. Brazil). In
other places, gasohol (ethanol mixed with petrol) is used.
• In alcoholic drinks: E.g. Ethanol in beers (from barley / prepared by fermentation), wines
(from grapes or rice / prepared by fermentation), brandy (from grapes / prepared by
fermentation plus distillation).
• Production of vinegar from ethanol. (See below.)
• Production of esters: (See below.)

Properties and reactions of alkanols

• Solubility: Lower alkanols (C1 – C3) are soluble in water (due to the hydroxyl group) and
in non-aqueous solvents (due to the hydrocarbon part of the molecule). Hence the are
used for mixing oils and water in cosmetics.
• Burning: Alkanols burns completely with hot clean blue flames. E.g. ethanol:
C2H5OH(l) + 3O2(g) ----> 2CO2(g) + 3H2O(l)

• Oxidation: Alkanols can be oxidised to alkanoic acids with potassium dichromate


solution acidified with dilute sulphuric acid. For example, oxidation of ethanol:

CH3CH2OH(l) + 2[O] ----> CH3COOH(aq) + H2O(l)


from the oxidising agent ethanoic acid
• Esterification: This is the reaction of an alkanol with an alkanoic acid to form an ester
and water. For example:
CH3COOH + CH3CH2OH -----> CH3COOCH2CH3 + H2O
ethanoic acid + ethanol ------> ethyl ethanoate + water
The lower esters are liquids with a sweet fruity smell. They are used as artificial flavours,
as fragrances for perfumes and cosmetics, and as solvents e.g. in nail polish remover and
some glues.

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Organic acids

• Organic acids are a homologous series with the general formula CnH2n+1COOH. All have
the -COOH group. The most common example is ethanoic acid CH3COOH.

Structural formula of ethanoic acid

Vinegar is a dilute solution of ethanoic acid. It is prepared industrially by adding suitable


micro-organisms to ethanol and exposing the mixture to air for 1 or 2 weeks.
• Ethanoic acid is a weak acid. It reacts slowly with some metals to give hydrogen, and with
carbonates to give carbon dioxide.

Problems associated with drinking alcohol

• Drinking even small amounts of alcohol can affect a person’s behaviour. For example, a
person is unable to see or speak clearly and unable to stand or walk properly.
• Continual drinking over a long period (e.g. several years) can cause health problems.
For example:
-- damage to the brain, liver and stomach.
-- some cancers, e.g. mouth, throat and gullet.
-- high blood pressure.
-- alcohol can pass from a mother to her unborn child and harm the baby.
• There are social and economic problems associated with alcohol. For example:
-- alcohol addiction.
-- family and work problems.
-- alcohol is a major cause of road accidents.
-- economic costs include hospital costs, legal costs and costs from lost work.

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22.1 – 22.4

Multiple-choice questions

1. The chemical name for the substance ‘alcohol’ is


A ethane
B ethene
C ethanol √
D ethanoic acid.

2. Which of the following are uses of ethanol?


(1) In alcoholic drinks.
(2) As a solvent for perfumes and cosmetics.
(3) As an alternative fuel for motor cars.
A (1) only
B (1) and (2) only
C (2) and (3) only
D (1), (2) and (3) √

3. Which of the following are examples of alcoholic drinks?


(1) Coca cola.
(2) Beer
(3) Wine
A (1) only
B (2) only
C (2) and (3) only √
D (1), (2) and (3)

4. What is the general formula for the alkanols?


A CnH2n+2
B CnH2n+1OH √
C CnH2n+2OH
D CnH2n+1COOH

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5. The diagram shows a ball-and-stick model of an alkanol. What is its name?

A Methanol.
B Ethanol. √
C Propanol.
D Butanol.

6. What is the systematic name of the alkanol with the following structural formula?
CH3 – CH2 – CH2 – CH2 – OH
A butanol.
B butanol-1.
C butan-1-ol. √
D butan-4-ol.

7. What compound is reacted with steam in the manufacture of ethanol?


A Ethene. √
B Ethane.
C Ethanoic acid.
D Glucose.

Questions 8 to 10 relate to the following alcoholic drinks:

A Beer.
B Wine.
C Brandy.
D Whisky.

8. Which drink is made by fermentation using grapes? B

9. Which drink is made by the fermentation of grapes followed by distillation of the


fermentation mixture? C

10. Which drink contains the lowest concentration of alcohol? A

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11. In the fermentation of a sugar, what are the final products?
A Water and carbon dioxide.
B Ethanol only.
C Ethanol and water.
D Ethanol and carbon dioxide. √

12. Methylated spirit is an industrial solvent and fuel. What does it consist of?
A Methanol.
B Ethanol.
C Methanol and ethanol. √
D Methanoic acid.

13. Some micro-organisms are added to a dilute solution of ethanol. The mixture is exposed
to the air for a few weeks. What is produced?
A Ethane.
B Ethane.
C An ester.
D Vinegar. √

14. Which of the following statements about esters is INCORRECT?


A They are found naturally in many fruits.
B They can be made from alkanols.
C Synthetic esters are added to foods and drinks as flavourings.
D They can be used as fuels instead of petrol. √

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Structured questions

1. The alkanols are a homologous series.


(a) (i) What is another name for the alkanols? __The alcohols.__________________
(ii) What is their general formula? _____CnH2n+1OH.______________________
(b) Name the first two alkanols and write the condensed structural formulae for each.
___1. Methanol, CH3OH. 2. Ethanol, CH3CH2OH._________________________
(c) What is common about the names of the alkanols?
__They all end in –ol.__________________________________________________
(d) What functional group do all alkanols have?
__The hydroxyl group, -OH.___________________________________________
(e) The third alkanol, C3H7OH exists as two isomers.
(i) What are isomers?
___Compounds with the same molecular formula but different structural formulae._
(ii) Write the name and structural formula for each of these isomers.
1.

2.

2. Ethanol can be manufactured from ethene.


(a) What other reactant is used? ____Steam._____________________________
(b) Write the equation for the reaction.
___C2H4(g) + H2O(g) -----> C2H5OH(g)______________________________
(c) What are the conditions for the reaction?
__High temperature (~300OC), high pressure, and a catalyst (phosphoric acid)._____

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3. Ethanol (alcohol) can also be prepared from the starch and sugars in plants. This method is
used to prepare alcoholic drinks.
(a) What is the process called?
___Fermentation.________________________________________________________
(b) Name TWO plants used for this process and the kind of alcoholic drink prepared from
each.
___E.g. 1. Grapes to make wine.____________________________________________
_______2. Barley to make beer._____________________________________________
(c) To prepare ethanol, a solution of glucose (a sugar) is mixed with some yeast.
(i) What is the purpose of the yeast?
___The yeast contains an enzyme which speeds up the process of the
fermentation._______________________________________________________
(ii) Write the equation for the formation of the ethanol.
___C6H12O6(aq) ----> 2C2H5OH(aq) + 2CO2(g)______________________________
(iii) Only a dilute solution of ethanol can be formed. What is the reason for this?
___At higher concentrations, the yeast dies and the fermentation stops.______________
_______________________________________________________________________
(iv) What can be done to increase the concentration of the ethanol?
___The fermentation mixture can be distilled to increase the concentration of the ethanol._

4. Some uses of alkanols.


(a) Alkanols can be used as solvents. State some uses of ethanol as a solvent.
___It is used as a solvent for perfumes, cosmetics, paints and dyes.___________________
(b) Briefly describe how vinegar is prepared from ethanol.
__Some suitable micro-organisms are added to a dilute solution of ethanol. The mixture is
exposed to the air for a few weeks. The ethanol is converted into ethanoic acid /
vinegar._______________________________________________________________
(c) In some countries, ethanol is used as a fuel instead of petrol.
(i) Name one such country. __Brazil.________________________________
(ii) State an advantage of ethanol over petrol.
__Ethanol burns more cleanly / causes less air pollution than petrol._________________
(iii) How is the ethanol produced?
__By the fermentation of sugar from sugar cane._________________________________

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5. Esters are naturally-occurring compounds and can also be made synthetically.
(a) State a property of esters that makes them important compounds.
__They have a strong, pleasant/sweet smell. _________________________________
(b) State where esters occur naturally.
__In many fruits and flowers.___________________________________________
(c) State THREE uses of synthetic esters.
__E.g. As solvents (e.g. nail polish remover), as flavouring for foods and rinks (e.g. jellies,
milk shakes), and to provide fragrance/ a sweet smell in perfumes. _____________

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22.5 – 22.6

Multiple-choice questions

1. Which of the following statements about the properties of alkanols is INCORRECT?


A The chemical properties of all alkanols are similar.
B The chemical properties of alkanols are due to the hydroxyl group, -OH.
C The lower alkanols are insoluble in water but soluble in non-aqueous solvents. √
D As the hydrocarbon part of the alkanol molecule increases, there is a gradual change in
physical properties.

2. Ethanol has the formula C2H5OH. Which of the following statements concerning this
formula is/are correct?
(1) The –OH part is responsible for all the properties of ethanol.
(2) The –OH part is soluble in water but not in oils.
(3) The C2H5- part is soluble in non-aqueous solvents such as oils.
A (1) only
B (1) and (2) only
C (2) and (3) only √
D (1), (2) and (3)

3. Which of the following statements about the combustion of alkanols is/are correct?
(1) They burn with a clean flame.
(2) The combustion is a redox reaction.
(3) Carbon dioxide and water are always formed.
A (1) only
B (1) and (3) only
C (2) and (3) only
D (1), (2) and (3) √

Questions 4 and 5 refer to the following types of reactions:

A Displacement.
B Redox.
C Esterification.
D Neutralisation

4. Some ethanol is added to acidified potassium dichromate solution. What type of reaction
occurs? B

5. What is the type of reaction between an alkanol and an alkanoic acid called? C

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Questions 6 and 7 refer to the ester formed when methanol and ethanoic acid react.

6. What is the name of the ester?


A Methyl methanoate.
B Methyl ethanoate. √
C Ethyl methanoate.
D Ethyl ethanoate.

7. What is the formula of the ester?


A CH3COOCH3 √
B CH3COOCH2CH3
C CH3CH2COOCH3
D CH3CH2OOCH2CH3

8. Which of the following is NOT a homologous series?


A Alkanes.
B Alkanols.
C Alkanoic acids.
D Esters. √

9. What substance is represented by the model in the diagram

A Ethanol.
B Ethanoic acid. √
C Methanoic acid.
D Ethyl ethanoate.

10. What is the name of the compound with the formula HCOOH?
A Methanol.
B Methanoic acid. √
C Ethanoic acid.
D Methyl methanoate.

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Structured questions

1. Alkanol molecules are made up of two parts.


(a) Name the two parts.
__1. The hydroxyl group, -OH. ____________________________________________
__2. A hydrocarbon part. / (Alkyl group.)____________________________________
(b) Identify the two parts in a molecule of ethanol, C2H5OH.
__C2H5- (the hydrocarbon part) and –OH (the hydroxyl group).___________________
(c) Which part is soluble in (i) water and (ii) oils?
__(i) The hydroxyl group. (ii) The hydrocarbon part._________________________
(d) Which part is mainly responsible for the chemical properties of an alkanol?
__The hydroxyl group._________________________________________________

2. The picture shows after-shave lotion. The lotion is a clear solution of water, oils and ethanol.

(a) Why are oils used in the after-shave lotion?


__To give the lotion a fragrance / pleasant smell._______________________________
(b) Why is ethanol included in the mixture?
__The ethanol dissolves both the water and the oils to give a clear mixture. Without the
ethanol, the oils would not mix with the water. ______________________________
_______________________________________________________________________

3. (a) What is an ester?


___A compound formed when an alkanol reacts with an alkanoic acid.___________
(b) Write the word equation for the formation of an ester.
__alkanoic acid + alkanol ---> ester + water_______________________________
(c) Do esters form a homologous series? ___No._____________________________
(d) State TWO properties of esters.
_1. They are liquids (at room temperature). __________________________________
__2. They have a sweet/pleasant smell. __________________________________
(e) Some esters occur naturally. Give TWO examples of where they are found.
__They occur in many fruits and flowers._________________________________

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(f) Some esters are made synthetically. Give some uses of these esters.
_E.g. 1. As flavourings in some foods and drinks. 2. To provide fragrance in perfumes and
other cosmetics. 3. Some are used as solvents, e.g. as nail polish remover.__________
_______________________________________________________________________

4. One ester is ethyl ethanoate.


(a) What alkanol is used to form this ester? __Ethanol.__________________________
(b) What alkanoic acid is used? __Ethanoic acid.____________________________
(c) Write the formula for the ester.
____CH3COOCH2CH3 ______________________________________________
(d) Write the chemical equation for the formation of this ester.
__ CH3COOH + CH3CH2OH -----> CH3COOCH2CH3 + H2O_____________
(e) There are many other esters.
(i) Write the name and formula for any ONE other ester.
__E.g. Methyl propanoate. CH3CH2COOCH3 ______________________________
(ii) Write the names and formulae of the alkanol and the alkanoic acid from which it is
formed.
__Methanol, CH3OH and propanoic acid, CH3CH2COOH_____________________

5. Write chemical equations for each of the following reactions:


(a) The combustion of (i) ethanol and (ii) methanol in air.
___(i) C2H5OH(l) + 3O2(g) ----> 2CO2(g) + 3H2O(l)________________________
___(ii) 2CH3OH(l) + 3O2(g) ----> 2CO2(g) + 4H2O(l)________________________
(b) Magnesium and ethanoic acid.
__2CH3COOH(aq) + Mg(s) ---> Mg(CH3COO)2(aq) + H2(g)_________________
(c) The formation of the ester you named in part (e) on Question 5.
__ CH3CH2COOH + CH3OH -----> CH3CH2COOCH3 + H2O________________

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22.7

Multiple-choice questions

1. Which part of the body removes alcohol?


A Brain.
B Stomach.
C Liver. √
D Muscles.

2. Approximately what volume of alcohol can the body remove per hour?
A 0.1 cm3
B 1.0 cm3
C 10 cm3 √
3
D 100 cm

Questions 3 and 4 relate to a person who drinks 3 cans of beer at a meal.

3. Approximately what volume of alcohol does the person consume?


A 3 cm3
B 30 cm3 √
C 60 cm3
D 600 cm3

4. How might this amount of alcohol affect the person? The person:
(1) has a relaxed feeling.
(2) become dizzy and cannot stand.
(3) is less alert.
A (1) only
B (2) only
C (1) and (3) only √
D (2) and (3) only

Questions 5 and 6 relate to the blood alcohol level (measured in mg per 100 cm3 of blood).

5. For driving in Hong Kong, what is the legal limit of the blood alcohol limit?
A 10
B 20
C 50 √
D 80

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6. This level can be reached by consuming how much alcoholic drink within an hour?
(1) 2 to 3 cans of beer.
(2) About 2 glasses of wine.
(3) About 2 small glasses of whisky
A (1) only
B (1) and (2) only
C (2) and (3) only
D (1), (2) and (3) √

7. What health problems can be caused by drinking alcohol over a long period of time?
(1) Liver damage.
(2) Heart and brain damage.
(3) Skin cancer.
A (1) only
B (1) and (2) only √
C (2) and (3) only
D (1), (2) and (3)

8. What social problems are associated with the drinking of alcohol?


(1) Addiction to alcohol.
(2) Family problems.
(3) Road accidents.
A (1) and (2) only
B (1) and (3) only
C (2) and (3) only
D (1), (2) and (3) √

9. What is the safe limit alcohol limit for a pregnant woman?


A No alcohol at all. √
B 1 to 2 cans of beer a day.
C 2 to 3 cans of beer a week.
D One bottle of wine a week.

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Structured questions

1. (a) State TWO negative effects of consuming a small amount of alcohol at one time.
__E.g. Speech can become slower. Decrease in alertness (increasing the chance of an
accident).__________________________________________________________
(b) State TWO effects of consuming a large amount of alcohol at one time.
_E.g. Unable to stand. Speech becomes difficult/slurred. May become unconscious.
__________________________________________________________________
(c) List some health problems that can occur with drinking over several years.
_E.g. Damage to body organs such as the liver, brain, heart and stomach. Cancer of the
mouth, throat and gullet. High blood pressure. Weight problems/obesity.
______________________________________________________________________
(d) Why is it harmful for a pregnant woman to consume alcohol?
__The alcohol can pass through the placenta from the mother to the unborn child. The
alcohol can damage the baby’s body and brain._____________________________
(e) List some social problems associated with alcohol.
_E.g. People can become addicted to alcohol. A heavy drinker can be aggressive to his
family. Some people with alcohol problems commit crimes.
______________________________________________________________________

2. (a) What is meant by ‘blood alcohol level (or concentration)’?


__The mass of alcohol (in milligrams) present in 100 cm3 of blood._________________
(b) What happens to this level as a person continues to drink?
__The level/concentration increases.__________________________________________
(c) (i) For driving in Hong Kong, what is the legal limit for blood alcohol level?
__50 mg/100 cm3 ________________________________________________________
(ii) Give an example of how much alcohol can be consumed within an hour to reach this
level?
__E.g. 2 to 3 cans of beer. / 2 glasses of wine.__________________________________
(iii) What is the instrument used by the Police to check a person’s blood alcohol level?
___A breathalyser.________________________________________________________

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