Chapter Four

Organic Chemistry

Chapter Four

Students Guide

Chapter Four
Organic Chemistry
Part (I): Hydrocarbons
Question (1)
(A) Given the following hydrocarbons:

(A)

(B)

(C)

(D)

(E)

1. Classify the above hydrocarbons to saturated and unsaturated.

Solution
Saturated hydrocarbons

Unsaturated hydrocarbons

(C) and (E)

(A), (B) and (D)

2. Classify the unsaturated hydrocarbons to alkenes and alkynes.

Solution
Alkenes

Alkynes

(A) and (D)

(B)

3. Calculate the number of sigma bonds found between:

(i) Carbon atoms in each hydrocarbon.
Solution
Hydrocarbon

No of sigma () bonds

(A)
(B)
(C)
(D)
(E)

3
2
3
6
5

Chapter Four

Students Guide

(ii) Carbon and hydrogen atoms in each hydrocarbon.

Solution
Hydrocarbon

No of sigma () bonds

(A)
(B)
(C)
(D)
(E)

8
4
10
14
14

4. What is the number of pi bonds in each unsaturated hydrocarbon?

Solution
Hydrocarbon

No of pi bonds

(A)
(B)
(D)

1
2
1

5. How many moles of hydrogen molecules are required to saturate each unsaturated
hydrocarbon?
Solution
Hydrocarbon

No of hydrogen molecules (H2) required

(A)
(B)
(D)

1
2
1

6. Which unsaturated hydrocarbon is considered symmetric alkene and which one is

asymmetric?
Solution
Hydrocarbon

Symmetric alkene

(A)
(D)

Asymmetric alkene

7. Give the name of each hydrocarbon according to IUPAC system.

Solution
Hydrocarbon

Name according to IUPAC system

(A)
(B)
(C)
(D)
(E)

2-butene
1-propyne
2-methyl propane
2,3,3-trimethyl-1-butene
3-methyl pentane

Chapter Four

Students Guide

8. Show which hydrocarbon(s) that:

(i) Remove the colour of bromine dissolved in CCl4.
(ii) Reacts by addition.
(iii) Add hydrogen bromide according to Markownikoffs rule.
(iv) Called isobutane.
Solution
Hydrocarbon
(A)
(B)
(C)
(D)
(E)

(i)

(ii)

(iii)

(iv)

(B) Saturated open chain hydrocarbon having 17 atoms in its structure

1. What is the number of carbon and hydrogen atoms in this compound?
Solution
Alkane (CnH(2n + 2)) n + 2n + 2 = 17 n = 5
Number of carbon atoms = 5 atoms
Number of hydrogen atoms = 12 atoms
2. Write the molecular formula of this hydrocarbon.
Solution
The molecular formula is C5H12

Chapter Four

Students Guide

3. Write the expected structural formulas, then name each one according to IUPAC
system.
Solution
Structural formula

Common name

IUPAC name

n-pentane

n-pentane

Isopentane

2-methyl butane

Neopentane

2,2-dimethyl propane

(C)
1. What is the molecular formula of cycloalkane having 15 atoms?
Solution
Cycloalkane (CnH2n) n + 2n = 15 n = 5
The molecular formula is C5H10
2. What is the number of hydrogen atoms in an alkene having 18 atoms?
Solution
Alkene (CnH2n) n + 2n = 18 n = 6
Number of hydrogen atoms = 12 atoms
3. What is the number of carbon atoms in an alkyne having 13 atoms?
Solution
Alkyne (CnH(2n 2)) n + 2n 2 = 13 n = 5
Number of carbon atoms = 5 atoms

Chapter Four

Students Guide

4. What is the number of carbon atoms that are found in naphthalene and diphenyl?
Solution
Number of carbon atoms in naphthalene = 10 carbon atoms
Number of carbon atoms in diphenyl = 12 carbon atoms

Chapter Four

Students Guide

Question (2)
Write molecular and structural formula for each of the following:
1. An open chain saturated aliphatic hydrocarbon having three carbon atoms.
2. An open chain saturated aliphatic hydrocarbon having ten hydrogen atoms.
3. A saturated cyclic hydrocarbon having six carbon atoms.
4. A saturated cyclic hydrocarbon having ten hydrogen atoms.
5. An unsaturated aliphatic hydrocarbon having four carbon atoms and two double bonds.
6. An unsaturated aliphatic hydrocarbon having a double bond and five carbon atoms.
7. An unsaturated aliphatic hydrocarbon having a double bond and eight hydrogen atoms.
8. An unsaturated aliphatic hydrocarbon having six carbon atoms and three triple bonds.
9. An unsaturated aliphatic hydrocarbon having a triple bond and three carbon atoms.
10. An unsaturated aliphatic hydrocarbon having six hydrogen atoms and a triple bond.
11. An unsaturated cyclic hydrocarbon having six carbon atoms and three double bonds.
12. An unsaturated cyclic hydrocarbon having ten carbon atoms and eight hydrogen atoms.
13. An alkene having six carbon atoms and does not contain methylene group (CH2) in its
structure.
14. Symmetric alkene having four carbon atoms.
15. An asymmetric alkene having four carbon atoms.
16. A saturated aliphatic hydrocarbon used to prepare benzene by catalytic reforming
method.
17. A saturated aliphatic hydrocarbon used to prepare toluene by catalytic reforming
method.
18. An unsaturated aliphatic hydrocarbon produced from thermal decomposition of ethyl
hydrogen sulphate at 180oC.
19. A saturated aliphatic hydrocarbon produces an unsaturated hydrocarbon and a saturated
one, each having four carbon atoms on thermal catalytic cracking.
20. A saturated cyclic hydrocarbon obtained on hydrogenation of benzene.
21. An unsaturated cyclic hydrocarbon obtained on cyclic polymerization of ethyne.
22. An alkane obtained on dry distillation of sodium propanoate (CH3CH2COONa) with soda
lime.
Solution
Molecular formula

1.

C3H8

2.

C4H10

Structural formula

Chapter Four

Students Guide

3.

C6H12

4.

C5H10

5.

C4H6

6.

C5H10

7.

C4H8

8.

C6H2

9.

C3H4

10.

C4H6

11.

C6H6

12.

C10H8

Chapter Four

Students Guide

13.

C6H14

14.

C4H8

15.

C4H8

16.

C6H14

17.

C7H16

18.

C2H4

19.

C8H18

20.

C6H12

Chapter Four

Students Guide

21.

C6H6

22.

C2H6

10

Chapter Four

Students Guide

Question (3)
Write the scientific expression for each of the following statements:
1.
2.
3.
4.
5.

Organic compounds are formed in the living cells by the influence of a vital force.
The formula that shows the type and number of atoms present in an organic compound.
Organic compounds composed of carbon and hydrogen only.
The presence of more than one organic compound having the same molecular formula.
A group of compounds having the same general molecular formula and graduated in
their physical properties.
6. Easy liquefied halogenated alkanes used in manufacture of cooling systems.
7. An organic atomic group that does not found alone and obtained by the removal of one
hydrogen atom from alkanes.
8. Saturated aliphatic hydrocarbons, their general molecular formula is CnH(2n + 2).
9. Saturated cyclic hydrocarbons their general molecular formula is C2H2n.
10. Unsaturated aliphatic hydrocarbons having a double bond in their structures.
11. The process of adding hydrogen to plant oils to convert it to an artificial fat.
12. The rule that governed the addition of asymmetric reagent (HX) to asymmetric alkenes.
13. The process of replacement of one hydrogen atom or more in the benzene ring by a nitro
group (NO2).
14. Reaction of benzene with alkyl halides in the presence of anhydrous aluminum chloride.
15. The process of replacement of one hydrogen atom or more in the benzene ring by a
sulphonic group (SO3H).
16. Combination of a large number of unsaturated simple molecules to form a large one.
17. The formula that indicates the number and type of atoms in the organic molecule and the
kind of linkage between the atoms by the covalent bonds.
18. The mixture of hydrogen and carbon monoxide, which is used as reducing agent in
Midrex furnace.
19. The mixture of caustic soda and quick lime.
20. Unsaturated aliphatic hydrocarbons their general formula is CnH(2n 2).
21. Addition of water to alkenes or alkynes in the presence of a catalyst.
22. Conversion of long chain hydrocarbons to shorter ones by the effect of heat, pressure
and a catalyst.
23. Combination of two monomers to form copolymer associated by losing a small molecule
such as water.
24. An international system used to form nomenclature of organic compounds based on the
number of carbon atoms in the longest continuous carbon chain.
25. Important organic compounds obtained by treatment of alkyl benzene sulphonic acid
with caustic soda.
Solution
1. Vital force theory
3. Hydrocarbons
5. Homologous series
7. Alkyl radicals
9. Cycloalkanes
11. Hydrogenation of oils
13. Nitration

2. Molecular formula
4. Isomerism
6. Freons
8. Alkanes
10. Alkenes
12. Markownikoffs rule
14. Friedel-Crafts Alkylation

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Chapter Four

Students Guide

15. Sulphonation
16. Addition polymerization
17. Structural formula
18. Water gas
19. Soda lime
20. Alkynes
21. Catalytic hydration
22. Thermal catalytic cracking
23. Condensation polymerization
24. IUPAC system
25. Synthetic detergent (sodium salt of alkyl benzene sulphonic acid)

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Chapter Four

Students Guide

Question (4)
(A) Write the IUPAC names for each of the following compounds:

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

Solution
1.
3.
5.
7.
9.

3-methyl-1-butene
3-methyl hexane
3-methyl-1-pentene
2,4,6-trinitro toluene
1-bromo-4-chloro-2-nitro benzene

2. 1-chloro-2-butene
4. 4,4-dimethyl-2-pentyne
6. 2,4-diphenyl pentane
8. Cyclopentane
10. 3-ethyl-1-hexyne

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Chapter Four

Students Guide

(B) Write the structural formula for the following compounds, then write their
correct IUPAC names:
1.
3.
5.
7.

3-bromo butane
3,4-dimethyl pentane
3-methyl-2-ethyl butane
3,4,4-trimethyl hexane

2.
4.
6.
8.

2-ethyl propane
4,4-dichloro pentane
2,3-diethyl butane
2-chloro-4-butyne

Solution
Structural formula

IUPAC Name

1.

2-bromo butane

2.

2-methyl butane

3.

2,3-dimethyl pentane

4.

2,2-dichloro pentane

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Chapter Four

Students Guide

5.

2,4-dimethyl pentane

6.

3,4-dimethyl hexane

7.

3,3,4-trimethyl hexane

8.

3-chloro-1-butyne

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Chapter Four

Students Guide

(C) Choose from column (B) and (C) the suitable for column (A)
(A)

(B)

(C)

Compounds

Structural formulae

Groups

1.
2.
3.
4.

Cyclohexane
2,3-dimethyl-2-butene
3-methyl-1-butyne
Ortho-nitro chloro
benzene
5. 2,3-dimethyl butane

(i) Alkane
(ii) Alkene
(iii) Alkyne
(iv) Aromatic compound
(v) Cycloalkane

(a)

(b)
(c)
(d)

(e)

(f)

(g)

(h)

(i)

Solution
1. (e) and (v)
3. (i) and (iii)
5. (b) and (i)

2. (c) and (ii)

4. (h) and (iv)

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Chapter Four

Students Guide

Question (5)
(A) An open chain saturated hydrocarbon its molecular formula is C6H14
1. Write the possible structural formula, one of them is hexane, two methyl pentanes and
two dimethyl butanes.
2. Write IUPAC names for each structure.
3. Show which of them is used to prepare benzene and what is the name of the method
used?
4. How to convert normal hexane to cyclohexane?
Solution
1.

2.

n-hexane

2-methyl pentane

3-methyl pentane

2,3-dimethyl butane

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Chapter Four

Students Guide

2,2-dimethyl butane

3. n-hexane is used to prepare benzene by catalytic reforming method.

4.
/ Pt

CH3 -(CH2)4 - CH3

n-Hexane

+ 3 H2

/pressure/catalyst

+ 4 H2

C6H12
Cyclohexane

(B) Unsaturated aliphatic hydrocarbon its molecular formula is C5H10

1. To what class of hydrocarbons it belongs?
2. Write the possible structural formula, two of them are pentenes and another two are
methyl butenes.
3. Write the IUPAC name for each formula.
4. Write the products of addition of the following reagents to each of them, then write
IUPAC names for these products.
(a) Hydrocarbon in presence of nickel.
(b) Bromine dissolved in carbon tetrachloride.
(c) Hydrogen chloride.
Solution
1. C5H10 belongs to alkenes.
2.

3.

1-pentene

2-pentene

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Chapter Four

Students Guide

2-methyl-1-butene

3-methyl-1-butene

2-methyl-2-butene

Cyclopentane

4. (In the same order)

(a)

n-pentane

n-pentane

2-methyl butane

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Chapter Four

Students Guide

2-methyl butane

2-methyl butane

(b)

1,2-dibromo pentane

2,3-dibromo pentane

1,2-dibromo-2-methyl butane

1,2-dibromo-3-methyl butane

2,3-dibromo-2-methyl butane

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Chapter Four

Students Guide

(c)

2-chloro pentane

2-chloro pentane or 3-choro pentane

2-chloro-2-methyl butane

2-chloro-3-methyl butane

2-chloro-2-methyl butane

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Chapter Four

Students Guide

(C) Vinyl acetylene is considered as one of the unsaturated hydrocarbons, which

is characterized by the presence of one double bond and one triple bond. It is
represented by the following structure:

1. Calculate the number of sigma and pi bonds in its structure.

Solution
7 sigma bonds and 3 pi bonds
2. How many moles of hydrogen are required to convert it to a saturated one?
Solution
3 hydrogen moles (H2)
3. Give the IUPAC name of the saturated compound obtained.
Solution
n-butane
4. What is the type of hybridization of carbon atoms number 1 and 2?
Solution
Hybridization type of carbon atom number 1 is sp2
Hybridization type of carbon atom number 2 is sp3
5. What is the value of the angle represented by number 3?
Solution
Value of the angle represented by number 3 is 120o

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Chapter Four

Students Guide

6. Poly vinyl acetylene is one of the polymers obtained by addition polymerization.

(a) What is meant by addition polymerization?
(b) Write the structure of three repeated units of vinyl acetylene.
Solution
a) Addition polymerization: Combination of a large number of unsaturated simple
molecules (monomer) to give giant molecules (polymer) having the same empirical
formula
b) Three repeated units (i.e. trimer)

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Chapter Four

Students Guide

Question (6)
(A) Choose from the below table the compound (or compounds) which:

(A)

(B)

(C)

(D)

(E)

(F)

1.
2.
3.
4.

Reacts with two moles of bromine giving a tetrabromo compound.

Reacts with one mole of bromine giving a monobromo compound.
Reacts with one mole of bromine giving a dibromo compound.
Reacts with two bromine molecules giving two compounds each one of them having
one bromine atom.
5. Reacts with hydrogen bromide and the addition obeys Markownikoffs rule.
6. Adds one mole of hydrogen and is converted to cycloalkane.
7. Its catalytic hydration gives an aldehyde.
8. Used to prepare an explosive compound.
9. Reacts by addition and substitution.
10. Having thee pi bonds.
Solution
(A)
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.

(B)

(C)

24

(D)

(E)

(F)

Chapter Four

Students Guide

(B) Use the following table to answer the questions below:

(A)

Methane

(B)

Ethene

(C)

Ethyne

(D)

Ethane

(E)

n-hexane

(F)

Propene

1. Write the structural formula for each compound in the above table.
Solution

(A)

(B)

(C)

(D)

(E)

(F)

2. Choose the compound (or compounds) which belongs to:

(a) Alkanes
(b) Alkenes
(c) Alkynes
(d) Asymmetric alkenes
Solution
(A)

(B)

(C)

(D)

(E)

(F)

(a)

(b)

(c)

(d)

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Chapter Four

Students Guide

3. Use the suitable compound which is used to obtain:

(Support your answers by chemical equations)
(a) A compound used in the manufacture of Dacron fibers
(b) Aromatic benzene (write the name of the method used)
(c) A compound was used as anesthetic substance
(d) An aldehyde
(e) Ethyl alcohol
(f) A polymer used in the manufacture of plastic sheets
(g) Ethane (using two different compounds)
Solution
OH

(a)

CH2 = CH2 + H2O + [O]

Ethylene

KMnO4
Alkali

OH

H2C

CH2
Ethylene glycol

Polymerization

Catalytic reforming is the name of the method used

(b)

(c)

(d)

/ Pt

CH3 -(CH2)4 - CH3

n-Hexane

Indirect sun light

CH4 + 3 Cl2

CH CH + H
Ethyne

+ 4 H2

OH

OH

H2SO4 (40 %)
HgSO4 (60oC)

CCl3H + 3 HCl
Trichloromethane
(Chloroform)

C-H

H-C

Vinyl alcohol

OH

(e)

(f)

CH2 = CH2 + H2O + [O]

Ethylene
n CH2 = CH2
Ethylene

KMnO4
Alkali

CH2
Ethylene glycol
CH2

(g)

CH
CH + 2 H
Ethyne

CH2
n

Polyethylene

H
CH2 + H
Ethylene

OH

H2C

1000 atmosphere
peroxide as initiator

CH2

CH3CHO
Ethanal
(Aceytaldehyde)

Heating / Pt

Heating / Pt

CH2
H2C
Ethane

CH3 - CH3

26

Dacron

Chapter Four

Students Guide

4. Show by chemical equations the apparatus used to prepare each of the following
gases in lab:
(a) Methane
(b) Ethene
(c) Ethyne
Solution
Anhydrous sodium acetate

* * *
* ** **

Soda lime

(a)

O
O
O
O
O
O

Methane
Water

Thermometer

Conc. H2SO4
and ethanol

(b)

*****
****
*

O
O O
OO
O
O
OO O

O
O
O
O
O
O

Ethylene

Water

sodium hydroxide solution

Water

(c)
Calcium carbide

*****
****
*

CuSO4 solution
in dil. H2SO4

O
O O
OO
O
O
OO O

27

O
O
O
O
O
O

Acetylene
Water

Chapter Four

Students Guide

5. How can you differentiate between:

(a) Ethane and propene
(c) Ethane and ethyne

(b) Methane and ethene

Solution
(a) By using Br2 solution in CCl4
Ethane is not affected while propene discharges the red colour of Br2
Br
CH3

CH2 + Br
CH
Propene

Br

CCl4

Br

CH3
CH2
HC
1,2-Dibromopropane

(b) By using Br2 solution in CCl4

Methane is not affected while ethene discharges the red colour of Br2
Br
CH2 + Br
CH2
Ethylene

Br

CCl4

Br

CH2
H2C
1,2-Dibromoethane

(c) By using Br2 solution in CCl4

Ethane is not affected while ethyne discharges the red colour of Br2
Br
CH
CH +
Ethyne

2 Br

Br

CCl4

H-C

Br
C-H

Br
Br
1,1,2,2-Tetrabromoethane

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Chapter Four

Students Guide

Question (7)
Choose the correct answer
1. The element which is found in the structure of all organic compounds is
(a) Hydrogen
(b) Carbon
(c) Nitrogen
(d) Oxygen
2. The organic compound obtained on heating an aqueous solution of silver cyanate and
ammonium chloride is
(a) Silver chloride
(b) Ammonium cyanate
(c) Urea
(d) Ammonium cyanide
3. Organic chemistry studies the chemistry of carbon compounds except
(a) Carbon oxides
(b) Salts of carbonate and bicarbonate
(c) Cyanide salts
(d) All the previous
4. The first scientist who prepared an organic compound in lab is
(a) Berzelius
(b) Whler
(c) Lavoisier
(d) Boyle
5. The number of carbon atoms in alkane having 14 hydrogen atoms is
(a) 14
(b) 7
(c) 6
(d) 5
6. The number of hydrogen atoms in an alkane having 5 carbon atoms is
(a) 5
(b) 12
(c) 14
(d) 10
7. The number of sigma bonds in an alkane having 4 carbon atoms is
(a) 4
(b) 8
(c) 10
(d) 13
8. Alkenes and alkynes are considered from hydrocarbons.
(a) Open chain saturated
(b) Unsaturated cyclic
(c) Open chain unsaturated
(d) Saturated cyclic
9. Saturated cyclic hydrocarbons which is composed of three carbon atoms or more are
called
(a) Alkanes
(b) Cycloalkanes
(c) Alkynes
(d) Aromatic compounds
10. The formula of the polymer used in covering non-stick pans is

(a)

(b)

(c)

(d)

11. All the following alkenes are symmetric except

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Students Guide

(a)

(b)

(c)

(d)

12. Addition of asymmetric reagent to asymmetric alkene obeys rule.

(a) Hunds
(b) Markownikoffs
(c) Schiffs
(d) Baeyers
13. Benzene may react by
(a) Substitution only
(c) Addition and substitution

(b) Addition only

(d) Elimination

14. The number of methyl groups (CH3) in 2-methyl pentane is

(a) 3
(b) 2
(c) 5

(d) 4

15. The number of methylene groups (CH2) in 2-methyl pentane is

(a) 3
(b) 5
(c) 2

(d) 4

16. The organic compound that have the molecular formula C3H6 is considered from
hydrocarbons.
(a) Unsaturated aliphatic
(b) Saturated aliphatic
(c) Unsaturated cyclic
(d) Aromatic
17. Cyclohexane is an example of hydrocarbons.
(a) Unsaturated aliphatic
(b) Saturated open chain aliphatic
(c) Saturated cyclic aliphatic
(d) Aromatic
18. Benzene and naphthalene are considered from hydrocarbons.
(a) Unsaturated aliphatic
(b) Saturated aliphatic
(c) Saturated cyclic
(d) Unsaturated cyclic (aromatic)
19. In homologous series, each compound exceeds the previous one by group.
(a) CH3
(b) C2H5
(c) CH2
(d) CH3CH2
20. The molecular formula of an alkene having 4 carbon atoms is
(a) C4H4
(b) C4H8
(c) C4H10
21. The chemical formula of 2-bromo-4-methyl pentane is
(a)

(b)

(c)

(d)

22. All the following chemical formula are correct except

(a)

(b)

30

(d) C4H3

Chapter Four

Students Guide

(c)

(d)

23. All these chemical formulae are incorrect except

(a)

(b)

(c)

(d)

24. The value of the angle between the bonds in cyclobutane is

(a) 109o28
(b) 107o
(c) 60o

(d) 90o

25. The most active compound from the following compounds is

(a) Cyclopropane
(b) Normal propane
(c) Cyclopentane
(d) Cyclohexane
26. The unsaturation in the organic compounds may be detected by
(a) Hydrogen peroxide
(b) Acidified potassium permanganate
(c) Bromine dissolved in carbon tetrachloride
(d) All the previous answers are right
27. Chlorination of nitro benzene gives
(a) Meta-chloro nitro benzene
(c) Para-chloro nitro benzene

(b) Ortho-chloro nitro benzene

(d) Mixture of (b) and (c)

28. Nitration of chloro benzene gives

(a) Meta-chloro nitro benzene
(c) Para-chloro nitro benzene

(b) Ortho-chloro nitro benzene

(d) Mixture of (b) and (c)

29. Manufacturing detergents is based on compound.

(a) Aromatic sulphonic acids
(b) Aliphatic sulphonic acids
(c) Salt of aromatic sulphonic acids
(d) Salt of aliphatic sulphonic acids

30. To prepare

we carry out

(a) Chlorination of benzene then nitration of the product

(b) Alkylation of benzene then nitration of the product

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(c) Nitration of benzene and alkylation of the product

(d) Nitration of benzene then chlorination of the product
31. Freons are composed of
(a) Carbon and hydrogen only
(c) Chlorine and fluorine only

(b) Carbon and chlorine only

(d) Carbon, fluorine and chlorine

32. Alkanes differ from alkenes because they are

(a) Hydrocarbons
(b) Saturated compounds
(c) Compounds that react by addition
(d) Their molecular formula is CnH2n
33. Bromine reacts with ethene and is obtained.
(a) Bromo ethane
(b) 1,2-dibromo ethene
(c) 1,2-dibromo ethane
(d) 1,1-dibromo ethane
34. Reaction between bromine and ethene takes place by
(a) Addition
(b) Condensation
(c) Neutralization
(d) There is no right answer
35. A pair of compounds which are considered as isomers is
(a) C2H4, C2H6
(b) C2H5OH, CH3OCH3
(c) C2H5COOH, CH3COOH
(d) C6H6, C6H12
36. Formation of polyethylene is considered an example of polymerization.
(a) Condensation
(b) Addition
(c) Substitution
(d) Elimination

37. This compound

Is obtained on adding HBr to

(a)

(b)

(c)

(d)

Solution
1. (b)
3. (d)
5. (c)
7. (d)
9. (b)
11. (d)
13. (c)
15. (c)
17. (c)
19. (c)
21. (c)

2. (c)
4. (b)
6. (b)
8. (c)
10. (a)
12. (b)
14. (a)
16. (a)
18. (d)
20. (b)
22. (a)

32

Chapter Four
23. (c)
25. (a)
27. (a)
29. (c)
31. (d)
33. (b)
35. (b)
37. (b)

Students Guide
24. (d)
26. (c)
28. (d)
30. (a)
32. (b)
34. (a)
36. (b)

33

Chapter Four

Students Guide

Question (8)
Give a scientific explanation for each of the following:
1. The failure of vital force theory by Whlers experiment.
2. The molecular formula is not enough to express a given organic compound.
3. Ethanol and dimethyl ether are isomers.
4. Ethane is a saturated hydrocarbon while ethylene is an unsaturated one.
5. Alkanes, alkenes and alkynes form homologous series.
6. Organic compounds does not conduct electricity.
7. The presence of a huge number of organic compounds.
8. Soda lime is used in preparation of methane, not caustic soda alone.
9. By 2020, the use of freons will be forbidden.
10. Halogenated alkanes have a great importance in our daily life.
11. Alkenes and alkynes are more reactive than alkanes.
12. Addition in alkenes takes place ion one step, where in alkynes it takes place in two steps.
13. Ethylene glycol is used as an antifreeze substance in car radiators.
14. Bromine dissolved in carbon tetrachloride is not used to differentiate between alkenes
and alkynes.
15. 1,2-dichloro ethane is not formed when vinyl chloride reacts with hydrochloric acid.
16. 1-chloro propane is formed when propene reacts with hydrogen chloride.
17. 1-butene is asymmetric alkene, while 2-butene is symmetric one.
18. Cyclopropane is more reactive than normal propane.
19. Both cyclopentane and cyclohexane are stable compounds.
20. DDT is used as an insecticide.
21. DDT is not used now as an insecticide in many countries.
22. Polychloro diphenyl is used as fire insulation.
23. TNT is used as an explosive.
24. Ethyne gas is passed in copper sulphate solution before collecting it.
25. Oxyacetylene flame is used for cutting and welding metals.
26. Detergents have a great role in removing stains and dirt from fabrics and clothes.
27. Nitration of chloro benzene gives two products, while chlorination of nitro benzene gives
one product.
28. The product of hydrolysis of ethyl hydrogen sulphate is different from the product of its
thermal degradation.
29. Baeyers reaction is used to detect the presence of double bonds.
30. Sometimes ethyne burns with a smoky flame.
31. Halothane is preferred than chloroform as anesthetic substance.
32. Hydration of ethene takes place in the presence of concentrated sulphuric acid.
33. Cigarette smoke has harmful effects on human health.

34

Chapter Four

Students Guide

Question (9)
Write chemical equations that illustrate each of the following:
1. Conversion of a normal alkane to a cycloalkane.
2. Obtaining acetaldehyde from calcium carbide.
3. Conversion of ethanol to ethane.
4. Hydrolysis and thermal decomposition of ethyl hydrogen sulphate.
5. Catalytic hydration of ethyne then oxidation of the product.
6. Formation of dihydric alcohol (ethylene glycol) from a monohydric alcohol (ethanol).
7. Conversion of acetylene to methane.
8. Addition of hydrogen bromide to propene.
9. Formation of 1,1-dibromo ethane from acetylene.
10. Preparation of benzene sulphonic acid from normal hexane.
11. Conversion of phenol to toluene.
12. Obtaining an insecticide from acetylene.
13. Conversion of normal alkane into a cyclic alkane.
14. Obtaining ortho and para, nitro chloro benzene from benzene.
15. Obtaining meta-nitro chloro benzene from benzene.
16. Passing phenol vapour over zinc dust then chlorination of the product.
17. Conversion of normal hexane into nitro benzene.
18. Dropping water over calcium carbide then passing the gas evolved over a red hot nickel
tube.
19. Formation of cycloalkane (cyclohexane) from sodium benzoate.
20. Conversion of phenol to gamixane.
21. Addition of hydrogen bromide to 2-methyl-1-propene.

35

Chapter Four

Students Guide

Question (10)
Polymers play a vital role in our daily life as they are used in many industries
1. What is meant by:
(a) Polymerization
(c) Condensation polymerization

(b) Addition polymerization

Solution
(a) Polymerization: It is combination of a large number of simple molecules (monomer) to
form giant molecules (polymer)
(b) Addition polymerization: Combination of a large number of unsaturated simple
molecules (monomer) to give giant molecules (polymer) having the same empirical
formula
(c) Condensation polymerization: Condensation of two different monomers with the
removal of a simple molecule to give a new monomer called copolymer that is the
basic unit for condensation polymerization
2. Show by chemical equations the steps of the formation of polyethylene.
Solution

3. Mention one use for each polymer from the following:

(a) Polyethylene
(b) Polypropylene
(c) Polyvinyl chloride
(d) Polytetrafluoro ethene
Solution
(a) Plastic sheets
(c) Drainage tubes

(b) Cans
(d) Cooking utensils

36

Chapter Four

Students Guide

4. The formula of the monomers used to prepare each of the following polymers:

(a)

(b)

Solution

(a)

(b)

5. Draw three repeated units (trimer), which is formed by addition polymerization of:
(a) Tetrafluoro ethene
(b) 2-methyl-2-propene
Solution

(a)

(b)

37

Chapter Four

Students Guide

Question (11)
Organic compounds react with different methods
Give an example for each reaction of the following:
1. Substitution and elimination reactions of ethane.
2. Addition reaction for ethene and another for ethyne.
3. Substitution and addition reactions for benzene.
4. Oxidation of ethylene by diluted alkaline KMnO4.
5. Combustion of ethyne and benzene.
6. Dry distillation of sodium acetate and sodium benzoate.
7. Thermal catalytic cracking of normal octane.
8. Catalytic hydration of ethene and ethyne.
9. Sulphonation of toluene and benzene.
10. Nitration of toluene and benzene.

38

Chapter Four

Students Guide

Chapter Four
Organic Chemistry
Part (II): Hydrocarbon Derivatives
Question (1)
I) A, B, C and D are four functional groups
(-OH)

(-O-)

(-CHO)

(-COOH)

(A)

(B)

(C)

(D)

1. Write the name of each function group.

Solution

Hydroxyl group

Etherial group

Formyl group

Carboxylic group

2. What is the class of the compounds having each of these functional groups?
Solution

alcohols or
phenols

ether

aldehyde

carboxylic acids

Chapter Four

Students Guide

3. Give an example for an organic compound represents each class?

Solution

Ethanol

Dimethyl ether

Ethanal

Ethanoic acid

4. Show by chemical equation how to convert an organic compound having the functional
group:
(a) (A) to another having a functional group (B)
Solution

(b) (D) to another having a functional group (A)

Solution

(c) (C) to another having a functional group (A)

Solution

(d) (A) to another having a functional group (C)

Chapter Four

Students Guide

II) Derivatives of hydrocarbons are characterized by the presence of a certain

functional group
Look at the following organic compound these answer the question below:

1. What are the functional groups found in the above compound?

Solution

2. Determine the functional group that:

(a) Cause effervescence when it reacts with NaHCO3.
(b) Responsible for the formation of a violet colour when treated with FeCl3.
(c) Forms an ester when it reacts with an alcohol.
(d) Forms an ester when it reacts with ethanoic acid.
(e) On ammonolysis gives acid amide and alcohol.
(f) Reacts with NaOH but cannot react with NaHCO3.
Solution

(a)

(b)
Carboxylic group

Hydroxyl group

Chapter Four

Students Guide

(c)

(d)

Hydroxyl group

Carboxylic group

(e)

(f)

Hydroxyl group

Ester group
III) Hydrocarbon derivatives are classified into derivatives having N atoms like
amines and derivatives having oxygen atoms such as alcohols, ethers,
aldehydes, ketones, phenols and acids
1. Write the general formula of each one of these classes.
Solution

Alcohols

Ethers

Aldehydes

Carboxylic acids

Phenols

Ketones

2. What is the functional group characteristic to each class?

Solution

Hydroxyl group
Etherial group
Ethers

Alcohols

Chapter Four

Students Guide

Formyl group
Aldehydes

Carboxylic group
Carboxylic acids

Hydroxyl group
Carbonyl group
Ketones

Phenols
3. Give an example for each class.
Solution

Ethanol
Alcohols

Dimethyl ether
Ethers

Ethanal
Aldehydes

Ethanoic acid
Carboxylic acids

Propanone
Phenol
Phenols

Ketones

Chapter Four

Students Guide

4. Show by chemical equation how to convert alcohols to:

(a) An alkene
(b) Ether
(c) Aldehyde
(d) Ketone
(e) Carboxylic acid
(f) Organic ester
Solution

(a)

(b)

180o C
Conc.

CH3CH2OH + H2SO4
Ethanol

Conc. H2SO4/140oC

2 CH3-CH2-O-H

CH2 = CH2 + 3 H2O

Ethene (Ethylene)

CH3-CH2-O-CH2-CH3 +

OH

(d)

K2Cr2O7/ H2SO4

CH3 - CH - CH3

CH3-CH2-OH

CH3 - C - CH3 +

H2O

Propanone (Acetone)

2-Propanol (Sec. alcohol)

(e)

H2O

Diethyl ether

Ethanol

K2Cr2O7/ H2SO4

Ethanol

(O)

CH3CHO

CH3COOH
Acetic acid

Acetaldehyde

(f)

CH3-COOH

Acetic acid

CH3-CH2-OH

H2SO4

Ethanol

CH3-C-O-C2H5 + H2O
Ethyl acetate ester

5. How to convert phenol to benzene and vice versa?

Solution
OH
+

+ ZnO

Zn

Phenol

Cl
FeCl3

+ Cl2

Indirect sun light

+ HCl
Chlorobenzene
OH

Cl
+

Na OH

300oC
300 atm. pressure

+ Na Cl
Phenol

Chapter Four

Students Guide

Question (2)
Choose the correct answer for each statement of the following:
1. Organic compounds which are formed by replacing one hydrogen atom or more in alkanes
by a hydroxyl group are called
(a) Alcohols
(b) Phenols
(c) Ethers
(d) Alkenes
2. 1-propanol is considered as alcohol.
(a) Secondary monohydric
(c) Primary dihydric

(b) Primary monohydric

(d) Tertiary monohydric

3. 1,2,3-trihyroxy benzene is known as

(a) Carbolic acid
(c) Catechol

(b) Phenol
(d) Pyrogallol

4. This alcohol

is considered a alcohol

(a) Primary
(c) Tertiary

(b) Secondary
(d) Alkane

5. Alkaline hydrolysis of 2-bromo propane gives

(a) Primary alcohol
(b) Secondary alcohol
(c) Tertiary alcohol
(d) Alkane
6. Catalytic hydration of propene gives
(a) Primary alcohol
(c) Tertiary alcohol

(b) Secondary alcohol

(d) Dihydric alcohol

7. Glucose (C6H12O6) is an example of

(a) Polyhydroxy aldehydes
(c) Polyhydroxy alcohols

(b) Polyhydroxy ketones

(d) Hydrocarbons

8. Boiling point of glycerol is higher than that of

(a) Ethanol
(b) Propanol
(c) Ethylene glycol
(d) All of them

is named as

9. The alcohol which have the following formula

(a) 2-methyl-3-propanol
(c) 3-methyl-2-propanol

(b) 2-methyl-3-butanol
(d) 3-methyl-2-butanol

10. All these alcohols are oxidized by acidified potassium permanganate except
(a) 2-methyl-2-propanol
(b) Ethanol
(c) Isopropanol
(d) Methanol
8

Chapter Four

Students Guide

11. When 2-propanol reacts with concentrated sulphuric acid at 180o is obtained.
(a) Propyne
(b) Ethyne
(c) Propene
(d) Butyne
gives

12. Oxidation of the alcohol of chemical formula

(a) Aldehyde only
(c) Aldehyde then carboxylic acid

(b) Ketone
(d) Ether

13. One of the following alcohols is a secondary alcohol.

(a) CH3CH2CH2OH
(b) HOCH2CH2CH3
(c) CH3CHOH-CH3
(d) (CH3)2CH-CH2OH
14. Reaction of phenol with formaldehyde in an acidic medium is an example for
polymerization.
(a) Condensation
(b) Addition
(c) Alcoholic
(d) All are correct
15. Reaction of acids with alcohols in the presence of a dehydrating agent is called
(a) Hydration
(b) Esterification
(c) Neutralization
(d) Oxidation
16. The carboxyl group is composed of groups.
(a) Hydroxyl and carbonyl
(b) Hydroxyl and formyl
(c) Hydroxyl and amino
(d) No correct answer
17. All these acids are mono carboxylic except acid.
(a) Propanoic
(b) Formic
(c) Ethanoic
(d) Phthalic
18. acid is an example of dibasic aromatic acids.
(a) Benzoic
(b) Phthalic
(c) Formic
(d) Oxalic acid
19. All the formulae represent esters except
(a)

(b)

(c)

(d)

20. All these compounds give effervescence with sodium bicarbonate except
(a) HCOOH
(b) C6H5COOH
(c) HCOOCH3
(d) CH3COOH

Chapter Four

Students Guide

21. Toluene is oxidized by air in the presence of V2O5 and gives

(a) Benzoic acid
(b) Phthalic acid
(c) Acetic acid
(d) All of them
22. Esters usually have pleasant odours, therefore they are used in the manufacture of
(a) Artificial colours
(b) Flavors
(c) Polymers
(d) Detergents
23. The raw material for the production of Dacron fibers is formed by condensation of
(a) Phthalic acid with ethylene glycol
(b) Terphthalic acid with glycerol
(c) Terphthalic acid with ethylene glycol
(d) Benzoic acid with ethylene glycol
24. Acid amides are obtained from ammonolysis of esters and their general formula is
(a) RCONH2
(b) RONH2
(c) RCOONH4
(d) RNH+4 Cl25. Glycine is considered from acids.
(a) Hydroxyl
(c) Amino

(b) Aromatic
(d) Fatty

26. Insulin molecule is composed of 51 amino acids and it is considered an example of

(a) Proteins
(b) Carbohydrates
(c) Fats
(d) Oils
27. Marookh molecule is obtained from the reaction of salicylic acid with
(a) Acetyl chloride
(b) Acetic acid
(c) Methanol
(d) Ethanol
28. The isomer of ethyl acetate is
(a) Ethyl formate
(c) Methyl formate

(b) Methyl propanoate

(d) Ethanoic acid

29. The isomer of methyl benzoate is

(a) Ethyl formate
(c) Ethyl benzoate

(b) Phenyl acetate

(d) Phenyl formate

30. Reduction of acetic acid by hydrogen in the presence of copper chromate gives
(a) Copper acetate
(b) Chromium acetate
(c) Ethanol
(d) Acetaldehyde
31. The chemical formula of the ester obtained from the reaction of acetic acid with methanol is

(a) CH3COOC2H5
(b) CH3COOCH3
(c) C6H5COOCH3
(d) HCOOCH3
32. All these chemical formulae do not represent esters except
(a) CH3OCH2COCH3
(b) C2H5COC2H5
(c) CH3OC6H5
(d) CH3COOC2H5

10

Chapter Four

Students Guide

33. Oil and fats are esters obtained from the combination of fatty acids with
(a) Ethanol
(b) Ethylene glycol
(c) Glycerol
(d) No correct answer
34. The ester that gives ethanoic acid on hydrolysis is
(a) C6H5COOCH3
(b) C2H5COOCH3
(c) CH3COOC2H5
(d) C2H5COOC2H5
35. The ester that gives benzamide on ammonolysis is
(a) C6H5COOCH3
(b) CH3COOC6H5
(c) CH3COOC2H5
(d) C2H5COOC2H5
36. The compound obtained from the following reaction is considered from

(a) Aldehydes
(c) Ethers

(b) Carboxylic acids

(d) Esters

37. The following reaction is called

(a) Polymerization
(c) Saponification

(b) Esterification
(d) Fermentation

38. The chemical formula that represents a trihydric alcohol is

(a)

(b)

(c)

(d)

Solution
1. (a)
3. (d)
5. (b)
7. (a)
9. (d)
11. (c)
13. (c)
15. (b)

2. (b)
4. (b)
6. (b)
8. (d)
10. (a)
12. (c)
14. (a)
16. (a)
11

Chapter Four
17. (d)
19. (b)
21. (a)
23. (c)
25. (c)
27. (c)
29. (b)
31. (b)
33. (c)
35. (a)
37. (d)

Students Guide
18. (b)
20. (c)
22. (b)
24. (a)
26. (a)
28. (b)
30. (c)
32. (d)
34. (c)
36. (c)
38. (b)

12

Chapter Four

Students Guide

Question (3)
Write the scientific expression for each of the following:
1. Aliphatic organic compounds having a hydroxyl group in their structures
2. Aromatic organic compounds having a hydroxyl group attached directly to the benzene ring.
3. Alcohols in which the carbinol group is attached with two alkyl groups and one hydrogen
atom.
4. Alcohols that give aldehydes then acid when they are oxidized .
5. Addition of water to alkene in presence of conc. H2SO4.
6. Organic compounds having (-CH2OH) group in their structures.
7. Polyhydroxy aldehydes or polyhydroxy ketones.
8. Alcohols in which the carbinol group is not attached any hydrogen atoms.
9. The product of oxidation of secondary alcohols.
10. Reaction of acid with alcohol in presence of conc. H2SO4.
11. Alcohols that are difficult to be oxidized by normal oxidizing agents such as acidified
KMnO4.
12. A type of bond, which is responsible for solubility of light alcohols in water and the increase
in their high boiling points.
13. Organic compounds having one carboxylic group or more.
14. The ester of glycerol with long chain fatty acids.
15. Reaction of ester with ammonia to give an acid amid and alcohol.
16. Reaction of carboxylic acid with sodium carbonate or bicarbonate.
17. Natural polymers arise from the condensation of alpha amino acids with each others.
18. An ester produced from the reaction of salicylic acid with acetic acid.
19. The number of carboxylic groups in an organic acid basicity of the acid.
20. Heating esters with strong alkaline solution.
Solution
1. Alcohols
3. Secondary alcohols
5. Catalytic hydration
7. Carbohydrates
9. Ketones
11. Tertiary alcohols
13. Carboxylic acids
15. Ammonolysis
17. Proteins
19. Basicity of acid

2. Phenols
4. Primary alcohols
6. Primary alcohols
8. Tertiary alcohols
10. Ester formation
12. Hydrogen bond
14. Triglyceride ester (Fat or oil)
16. Acidity test
18. Acetylsalicylic acid
20. Saponification

13

Chapter Four

Students Guide

Question (4)
Write the molecular and structural formula for each of the following then write
their names:
1. Hydroxy aromatic compound in which the benzene ring is attached directly by two hydroxyl
groups.
2. Polyhydroxy aldehyde having six carbon atoms.
3. Polyhydric alcohol having six carbon atoms.
4. Dicarboxylic acid in which the number of carbon atoms in its structure in equal to the
number of carboxyl groups.
5. An acid amide obtained from ammonolysis of ethyl benzoate.
6. A hydroxyl aromatic acid used to prepare aspirin and Marookh oil.
7. Monocarboxylic aliphatic acid extracted from butter.
8. An alcohol obtained from hydrolysis of both ethyl acetate and ethyl benzoate.
9. An organic ester obtained from the reaction of salicylic acid with methyl alcohol.
10. The raw material used in the manufacture of Dacron fibers.
11. Dibasic aromatic acid.
12. A compound obtained from nitration of phenol.
13. A compound obtained when isopropanol is oxidized by acidified potassium permanganate.
14. An alkene, which gives a tertiary alcohol on catalytic hydration.
15. The product of heating chloro benzene with sodium hydroxide under high pressure.
16. An alkyl halide, which gives a tertiary butyl alcohol on alkaline hydrolysis.
17. An alkyl halide, which gives 2-butanol on alkaline hydrolysis.
18. A compound obtained when ethanol is heated with conc. sulphuric acid to 140oC.
Solution
Structural formulae

Molecular formulae

Names

1.

C6H6O2

Catechol

2.

C6H12O6

Glucose

14

Chapter Four

Students Guide

3.

C6H14O6

Sorbitol

4.

C2H2O4

Oxalic acid

5.

C7H7ON

Benzamide

6.

C6H6O

Phenol

7.

C4H8O2

Butanoic acid

8.

C2H6O

Ethanol

9.

C8H8O3

Methyl salicylate

15

Chapter Four

Students Guide

10.

C2H6O2

Ethylene glycol

11.

C8H6O4

Phthalic or
terphthalic

12.

C6H3O7N3

2,4,6-trinitro
phenol

13.

C3H6O

Propanone
(acetone)

14.

C4H8

2-methyl-1propene

15.

C6H6O

Phenol

16

Chapter Four

Students Guide

16.

C4H9Cl

2-chloro-2methyl propane

17.

C4H9Cl

2-chloro butane

18.

C4H10O

Diethyl ether

17

Chapter Four

Students Guide

Question (5)
Write scientific reasons for the following:
1.
2.
3.
4.
5.

Ethanol is a petrochemical.
Boiling point of ethanol is higher than that of the corresponding alkane.
Boiling point of glycerol is higher than that of ethylene glycol.
Methanol is added to ethanol during the manufacture of converted alcohol.
Alkyl iodide is preferred than alkyl chloride in the preparation of alcohols by hydrolysis of
alkyl halides.
6. Phenol is more acidic than ethanol.
7. Reaction of ethanol with H2SO4 is temperature dependent.
8. Oxidation of primary alcohols occurs in one step.
9. It is difficult to oxidize 2-methyl-2-butanol,
10. Iron III chloride is used to differentiate between carbolic acid and ethanol.
11. Both glycerol and phenol are used in the manufacture of explosives.
12. Ethanol does not react with sodium hydroxide while phenol does.
13. Phenol does not react with hydrogen chloride while ethanol react does.
14. Conc. sulphuric acid is added in ester formation and nitration.
15. Bakelite is used in the manufacture of electric instruments.
16. Boiling points of carboxylic acids is higher than that of the corresponding alcohols.
17. Boiling points of esters are lower than those of the acids and alcohols forming them.
18. Citric acid is added to frozen fruits.
19. Esters are use in the manufacture of perfumes and flavours.
20. Formation of esters from acids and alcohols takes place in the presence of dehydrating
gents.
21. Benzoic acid is monobasic whereas oxalic acid is a dibasic one.
22. Aspirin is preferred than salicylic acid in treatment of headache and cold.
23. Some types of aspirin is mixed with aluminum hydroxide.
Solution
4. To make it toxic and prevent its using as liquors or perfumes and to be used only as fuel and
in industrial process
13.

As a result of the aryl group, the bond between the ring and oxygen atom is short and
strong, cant be broken easily

18

Chapter Four

Students Guide

Question (6)
(I) Choose from columns (B) and (C), the suitable for column (A)
(A)
1.
2.
3.
4.
5.
6.

Ethanol
Acetone
Ethylene glycol
Carbolic acid
Glycerol
Isopropanol

(B)

(C)

Trihydric alcohol
Secondary alcohol
Ketone
Primary
monohydric
alcohol
(e) Phenol
(f) Dihydric alcohol
(g) Secondary monohydric
alcohol

(i) Used to prepare picric

acid
(ii) Cosmetics substance
(iii) Obtained on hydrolysis
of 2-bromo propane
(iv) Viscous liquid used in
hydrolytic brakes
(v) It obtained on the
oxidation of a secondary
alcohol
(vi) Used to prepare
converted alcohol
(vii) It is produced on
oxidation of a primary
alcohol

(a)
(b)
(c)
(d)

Solution
1. (d) and (vi)
3. (f) and (iv)
5. (a) and (ii)

2. (C) and (v)

4. (e) and (i)
6. (g) and (iii)

19

Chapter Four

Students Guide

(II) Choose from columns (B) and (C), the suitable for column (A):
(A)
1.
2.
3.
4.
5.
6.
7.

Benzoic acid
Salicylic acid
Phenyl acetate
Methyl benzoate
Glycine
Marookh oil
Aspirin

(B)

(C)

(a)

i.

Its ammonolysis gives

benzamide

(b)

ii. Obtained
from
the
reaction of acetic acid
with salicylic acid
iii. Monobasic aromatic acid
iv. From amino acids
v. Obtained
from
the
reaction of salicylic acid
with methanol

(c)

vi. Its ammonlysis

acetamide

gives

vii. Aromatic acid has two

different
functional
groups

(d)

viii.

(e)

(f)

(g)
(h)
(i)

20

Contain vitamin (C)

Chapter Four

Students Guide

Solution
1.
3.
5.
7.

(d) and (iii)

(i) and (vi)
(h) and (iv)
(f) and (ii)

2. (e) and (vii)

4. (a) and (i)
6. (b) and (v)

21

Chapter Four

Students Guide

Question (7)
I)
(a)

2-propanol

(b)

1-propanol

(c)

Picric acid

(d)

2-methyl-1-propanol

(e)

2-methyl-2-propanol

(f)

Catechol

Choose from the above table, the compound (or compounds) that considered
from
1.
2.
3.
4.
5.
6.
7.
8.

Primary alcohols
Secondary alcohols
Phenols
Alcohols which give aldehydes on oxidation
Alcohols which give ketones on oxidation
Product of nitration of phenol
Disubstituted benzene
Tetrasubstituted benzene

Solution

1.

(a)

(b)

(c)

(d)

(e)

(f)

2.

3.

4.

5.

6.

7.

8.

II)
(a)

Acetic acid

(b)

Formic acid

(c)

Oxalic acid

(d)

Ethyl formate

(e)

Methyl acetate

(f)

Ethyl acetate

(A) Choose from the above table the compound (or compounds) that considered
1. Monocarboxylic acids
2. Organic esters
3. Dibasic acids
4. Esters of ethanoic acid
Solution

1.

(a)

(b)

2.

(c)

22

(d)

(e)

(f)

Chapter Four

Students Guide

3.

4.

(d)

(e)

(f)

(B) From the table find:

1. Two isomers
2. Two compounds that give acetamide on ammonolysis
3. Compound that give effervescence with NaHCO3
4. Compound that is named according to IUPAC ethyl methanoate
Solution

1.

(a)

(b)

(c)

2.

3.

4.

III)

(a)

(b)

(c)

(d)

(e)

(f)

Choose from the above table, the compound (or compounds) which
1.
2.
3.
4.
5.
6.
7.

Have two different functional groups

Difficult to be ionized by normal oxidizing agents
Consider an isomer of ethanol
Obtained on heating ethanol with conc. H2SO4 at 140oC
Consider from phenols
Used in manufacture of Dacron fibers
Can be obtained, when water is added to 2-methyl-1-propene

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Chapter Four

Students Guide

8. Considered from ethers

Solution

1.

(a)

(b)

(c)

2.

3.

4.

5.

6.

7.

8.

24

(d)

(e)

(f)

Chapter Four

Students Guide

Question (8)
Aspirin and Marookh oil are used as medical esters and they derived from salicylic
acid.
Look at the following structures then answer the below questions:

(A)

(B)

Which formula represents Aspirin and which one represents Marookh oil, then show:
Solution
(A) is Aspirin

(B) is Marookh oil

1. The method used to prepare each of them.

Solution
Method used to prepare Aspirin:

COOH

O H
+
Salicylic acid

COOH

O
O -C-CH3

HO C-CH3

+ H -OH

Acetic acid

Acetyl salicylic acid (Asprine)

Method used to prepare Marookh oil:

O

C- OH

C- O-CH3

HO

HO
+
Salicylic acid

H O-CH3

Methanol

H -OH

Methyl salicylate (Marookh oil)

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Chapter Four

Students Guide

2. The type and number of functional groups in each of them.

Solution
(A)

(B)

3. The compound that gives violet colour with iron III chloride (explain why?).
Solution
Compound (B) gives violet colour with FeCl3 solution (It is considered from phenols)
4. The compound that cause effervescence when it reacts with sodium bicarbonate (explain
why?).
Solution
Compound (A) gives effervescence with NaHCO3 (It has free carboxylic group)
5. The product of reacting each of them with NaOH on cold.
Solution
[On cold no saponification occurs, only neutralization]
Reacting Aspirin with NaOH on cold:

26

Chapter Four

Students Guide

Reacting Marookh oil with NaOH on cold:

6. The product of ammonolysis of each them.

Solution
Ammonolysis of Aspirin:

Ammonolysis of Marookh oil:

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Chapter Four

Students Guide

Question (9)
Write the chemical equations that illustrate each of the following:
1. Formation of acetic acid from petrochemical product.
2. Hydrolysis of sodium ethoxide.
3. Effect of mixture of conc. nitric and sulphuric acids on both glycerol and phenol.
4. Conversion of primary alcohol to secondary one.
5. Formation of dihydric alcohol from a monohydric one.
6. Preparation of diethyl ether from ethyl iodide.
7. Oxidation of isopropyl alcohol by acidified potassium permanganate.
8. Conversion of phenol to benzene and vice versa.
9. Conversion of ethane to ethanol and vice versa.
10. Reaction of phenol with formaldehyde in acidic or basic medium.
11. Obtaining ethyl acetate from ethanol.
12. Addition of water to 2-methyl-2-butene.
13. Alkaline hydrolysis of tertiary butyl chloride.
14. Reaction of benzoic acid with ethanol in the presence of dry HCI then reacting the product
with ammonia.
15. Oxidation of toluene with air in the presence of V2O5 then neutralizing the product with
caustic soda solution.
16. Catalytic hydration of acetylene then oxidation of the product.
17. Effect of methanol and acetic acid on phenol.
18. The product of hydrolysis and ammonolysis of these esters.
(a) CH3CH2COOC6H5
(b) C6H5COOCH2CH3
19. Condensation of ethylene glycol with terphthalic acid.
20. Obtaining ethyl acetate from ethyl iodide.
21. Conversion of benzene to benzamide.
22. Obtaining toluene from sodium benzoate.
23. Conversion of acetic acid to normal ether.
24. Obtaining an acid amide from ethanol.

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Chapter Four

Students Guide

Question (10)
Answer the following questions:
1. Organic compounds play an important role in our daily life
Mention the economic importance of each of the following:
(a) Aspirin
(c) Oil and fats
(e) Esters
(g) Sodium benzoate
(i) Salicylic acid
(k) Ethanol
(m) Glycerol
(o) Bakelite

(b)
(d)
(f)
(h)
(j)
(l)
(n)
(p)

Dacron fibers
Alpha amino acids
Citric acid
Maroohk oil
Acetic acid
Ethylene glycol
Phenol
Picric acid

(b)
(d)
(f)
(h)
(j)
(l)
(n)
(p)

Manufacture of artificial heart valves

Building units of proteins
Retain colour and taste of fruits
Release rheumatic pains
Manufacture of synthetic silk
Manufacture of Dacron
Dyes, salicylic acid
Explosive and burns treatment

Solution
(a) Release headache and cold
(c) Manufacture of soap
(e) Food flavor
(g) Food preservative
(i) Manufacture of aspirin
(k) Normal and car fuel
(m) Skin cream and explosives
(o) Ash tray

2. Write the structural formulae for three isomers of alkyl halides having molecular formula
(C4H9Br), and then write the product of alkaline hydrolysis of each isomer.
Solution

1-bromo butane
(A)

2-bromo butane
(B)

Alkaline hydrolysis of each isomer:

29

2-bromo-2-methyl propane
(C)

Chapter Four

Students Guide

3. The following names organic compounds are incorrect, write their structures and correct
names according to IUPAC system.
(a) 3-ethyl-2-butanol
(c) 2-methyl-4-pentanol

(b) 3-methyl-3-butanol
(d) 3-butanol

Solution

(a)

3-methyl-2-pentanol

(b)

2-methyl-2-butanol

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Chapter Four

Students Guide

(c)

4-methyl-2-pentanol

(d)

2-butanol

4. Write the structural formulae for three isomeric alcohols having molecular formula:C4H10O
then:
Solution

1-butanol
(A)

2-butanol
(B)

2-methyl-2-propanol
(C)

(a) Classify each of them to primary, secondary and tertiary alcohols.

Solution
(A) is a primary alcohol
(C) is a tertiary alcohol

(B) is a secondary alcohol

(b) Explain the product of oxidation of each one.

Oxidation of (A):

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Chapter Four

Students Guide

Oxidation of (B):

Oxidation of (C):

(c) Write products of reaction of each of them with ethanoic acid.

Solution

(A)

(B)

(C)

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Chapter Four

Students Guide

(d) Write products of reaction of each of them with conc.H2SO4 at 140oC.

Solution
(A)

(B)

(C)

(e) What is the structural formula of the alkene produced by removal of water from each of
them when they are heated with conc. H2SO4 at 180oC?
Solution

33