Exam Night Rev ision Chapt er 5 Organic Chemist ry

Alkane – Alkene – Alkyne - Cycloalkane

IUPAC and isomers

1- Name the following according to the IUPAC system:

CH3 – CH – CH3 CH3 – (CH2)3 – CH2 – C(CH3)3

C3H7

Cl Br NO2 CH3 – CH = CH – CH2 – CH2Cl

CH3 – CH – CH – CH2 – CH – CH3

C2H5 Br

CH3 – CH – CH2 – C  CH CH3 – CH2 – C – C  CH

CH2 – CH2 – CH3

Br – CH2 – CH = CH – CH2Cl CH3 – CH – CH2 – CH2

C6H13 C6H5

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 1

2- The number of methylene groups in 2,2 – dimethyl butane is equal to the
number of methyl groups in ……….
a) propene
b) propane
c) pentane
d) ethyne
3- The number of gaseous compounds in alkenes ……….
a) 5
b) 4
c) 3
d) 2
4- The IUPAC name of CH2CHCCl3 is …………
a) 1,1,1 – trichloro – 2 – propene
b) 3,3,3 – trichloro – 1 – propene
c) 1,1,1 – trichloro – 3 – propene
d) 3,3,3 – trichloro – 2 – propene
5- What is the correct IUPAC name of 2 – ethyl – 3 – methyl butane?
a) 3 – ethyl – 2 – methyl butane
b) 2,3 – dimethyl pentane
c) 3 – methyl pentane
d) 3,4 – dimethyl pentane
6- Hydrogenation of ……… gives an isomer of 2,2 – dimethyl propane.
a) propene
b) 2 – methyl propene
c) 1 – pentene
d) 2 – methyl – 2 – pentene
7- The formula CH3 CH3 , after correct rewriting this compound, without
CH3 = CH – CH = CH3
changing its molecular formula, it will represent a compound ………….
a) branched alkene
b) unsaturated
c) alkene
d) open chain aliphatic

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 2

8- The compounds that could be similar in physical and chemical properties are
a) C8H18 , C18H38
b) C3H4 , C8H16
c) C3H6 , C16H32
d) C20H42 , C18H38

Chemical reactions
9- On detection of carbon and hydrogen in an organic compound, we can use all
the following to detect the produced carbon dioxide except ……….
a) KOH
b) Ca (OH)2
c) Ba (OH)2
d) Sr (OH)2
Dry distillation

10- Study the following figure then answer the following question:

The chemical formula of gas X is …………

a) CH4
b) CH3 - CH2 - CH3
c) CH3 - (CH2)2 - CH3
d) CH3 - (CH)2 - CH3

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 3

11- Dry distillation for CH3 - CH (C2H5) - COONa gives ………
a) 2 - methyl butane
b) 2 - methyl propane
c) butane
d) propane

Combustion

12- Hydrocarbon molecule contains number of carbon atoms = (n) so, complete
burning of 1 mole of it produces ………. moles CO2 and ………. moles of H2O.
For alkane ………………………………………………………………………….
For alkene …………………………………………………………………………….
For alkyne ……………………………………………………………………………

13- The following graph represents the

relation between the number of moles of
water vapor and the number of moles of
carbon dioxide which are produced from
complete combustion of 1 mole of
different hydrocarbons, which of the
following choices represents these
compounds?

Choices A B C
A C3H8 C2H2 C6H14
B C3H8 C2H4 C6H12
C C3H6 C2H2 C6H12
D C3H8 C2H2 C6H12

14- 0.1 mole of saturated open chain hydrocarbon completely combusted in

excess oxygen giving 0.3 mole of carbon dioxide, the hydrocarbon is ..................
a) C3H8
b) C4H10
c) C6H14
d) C6H12

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 4

15- 0.2 mole of alkane completely combusted in excess of oxygen giving 1 mole of
water, the alkane is ..............
a) C5H12
b) C4H10
c) C6H14
d) C2H8

16- 1 mole of alkane ............. produces 220gm from CO2 when it is burning
(C=12, O=16)
a) propane
b) butane
c) pentane
d) hexane

17- On complete combustion of 1 mole of aliphatic alkane by excess amount of

oxygen then passing the produced water vapor on anhydrous copper sulphate, its
mass increased by 72gm so, the alkane was ...............
a) C3H8
b) C4H10
c) C5H12
d) C6H14

Thermal catalytic cracking

18- Thermal catalytic cracking of octane produces 2 compounds X and Y.
Compound X removes the color of potassium permanganate in alkaline medium
so, compound Y may be ................
a) C2H2
b) C7H16
c) C6H14
d) C2H4

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 5

 Addition reactions

19- The following compound is produced from the reaction of ............. with
potassium permanganate in alkaline medium.
a) 2 – methyl – 2 – butene
b) 2 – methyl – 1 – butene
c) 3 – methyl – 1 – butene
d) 3,3 – dimethyl – 1 – propene

20- On adding potassium permanganate solution in alkaline medium to 4 –

methyl – 2 – pentene, the product will be .............
a) 1,2 – dihydroxyl – 4 – methyl pentane
b) 3,4 – dihydroxyl – 2 – methyl pentane
c) 2,3 – dihydroxyl – 4 – methyl pentane
d) 2,3 - dihydroxyl – 2 – methyl pentane

21- On adding potassium permanganate solution in alkaline medium to the 2

substances A and B separately, it is observed that the color disappears with
substance A only and doesn’t disappear with B, which of the following statements
is correct?
a) Compound A is 2 – methyl – 2 – pentene, the addition is done to carbon atoms number 2,3.
b) Compound A is 2 – methyl – 2 – pentene, the addition is done to carbon atoms number 1,2.
c) Compound B is propene, the addition is done to carbon atoms number 2,3.
d) Compound B is propene, the addition is done to carbon atoms number 1,2.

22- The following table represents the molecular formulas of X and Y substances:
X Y
C2H2Br2 C4H6

On adding a mole of bromine dissolved in carbon tetra chloride to a mole of X and

Y, which of the following statements is correct?
a) bromine color is removed with X and isn’t removed with Y.
b) bromine color isn't removed with X and also isn’t removed with Y.
c) bromine color is removed with X and is removed with Y.
d) bromine color isn’t removed with X and is removed with Y.

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 6

23- 0.5 mole of hydrocarbon compound reacts with 1 mole of bromine dissolved
in carbon tetra chloride; the formula of the producing compound is ...............
a) CnH2nBr2
b) CnH2n – 2Br2
c) CnH2nBr4
d) CnH2n – 2Br4

24- Each molecule of 2.1gm of alkene contains only 1 pi bond reacts with 8gm of
bromine dissolved in carbon tetra chloride until the color of Br2 completely
disappears. By knowing that the molar mass of Br2 = 160gm/mole. So, the formula
of alkene is .............. [C=12, H=1]
a) C5H10
b) C4H8
c) C3H6
d) C2H4

25- How many moles of hydrogen molecules are needed to convert 1 mole of the
following compound: CH2CHCBrCHCl to saturate compound?
a) 1 mole
b) 2 moles
c) 3 moles
d) 4 moles
26- To convert 1 mole of the opposite compound into
saturated one by hydrogenation ................ mole of
hydrogen is (are) required and gives ..............
a) 1 mole / ethyl cyclohexane
b) 2 moles / ethyl cyclohexane
c) 4 moles / ethyl benzene
d) 2 moles / ethyl cyclohexene

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 7

27- 1 mole of unsaturated hydrocarbon reacted with 3.612 × 1024 hydrogen atoms
to give saturated compound CxHy so, the molecular formula of unsaturated
hydrocarbon is ..............
a) CxHy + 6
b) CxHy – 6
c) CxHy + 12
d) CxHy – 3
+ 𝐱𝐁𝐫𝟐 /𝐂𝐂𝐥𝟒 + 𝐲𝐁𝐫𝟐 /𝐔𝐕
28- 1 mole of C2H2 → A→ C2Br6. So, the value of (x + y) is ...........
a) 1
b) 2
c) 3
d) 4
Markonikoff’s Rule
29- 2,2 – dibromo propane is produced from the reaction of ..............
a) propene with bromine solution in carbon tetra chloride.
b) propene with hydrogen bromide.
c) propyne with bromine solution in carbon tetra chloride.
d) propyne with hydrogen bromide.

30- When the opposite compound reacted with

excess of hydrogen bromide, which double bond will
apply Markonikoff’s Rule?
a) b only
b) a and b only
c) b and c only

31- The following reactions to get A, B, and C:

𝑺𝒕𝒓𝒐𝒏𝒈 𝒎𝒊𝒏𝒆𝒓𝒂𝒍 𝒂𝒄𝒊𝒅 ∆ 𝐇𝐲𝐝𝐫𝐨𝐠𝐞𝐧𝐚𝐭𝐢𝐨𝐧
R – CH2OH → A→B→ C. By knowing that B applies
Markonikoff’s Rule. So, A, B, and C are ...............
a) A: ethyl hydrogen sulphate, B: ethene, and C: ethane
b) A: ethene, B: ethyl hydrogen sulphate, and C: ethane
c) A: propyl hydrogen sulphate, B: propene, and C: propane
d) A: propene, B: propane, and C: propyl hydrogen sulphate

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 8

Polymerization by addition
32- The used monomer in the preparation of the opposite
polymer
a) 1,1,2 – trimethyl ethene
b) 2 – methyl – 2 – butene
c) 2 – methyl – 1 – butene
d) 2 – butane

33- In the presence of suitable pressure, temperature, and initiator, we can

convert CH3 – CH2 – CH = CH – CH2 – CH2 – CH3 into ..................

34- By replacing 1 hydrogen atom of ethene by methyl group then polymerized the
produced compound, the product is used in .................
a) shoes and hoses
b) plastic bottles
c) layering cooking utensils
d) carpets

Chemical activity

35- 2 organic compounds A and B from open chain hydrocarbon, compound A has
3 carbon atoms while compound B has 6 carbon atoms, and B is more active than
A. Then A and B are ..............
a) A: is a gaseous alkane, B: is a liquid alkene
b) A: is a liquid alkane, B: is a liquid alkene
c) A: is a gaseous alkane, B: is a gaseous alkene
d) A: is a gaseous alkane, B is a liquid alkane

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 9

36- Which of the following properties is correct about cyclobutane?
a) Is less active than cyclopentane
b) Is more stable than normal pentane
c) Burns faster than cyclopentane
d) Burns slower than normal pentane

Conversions
37- To obtain methane from calcium carbide we follow which of the following
sequence?
a) Catalytic hydration – oxidation – dry distillation.
b) Dropping water – catalytic hydration – oxidation – neutralization – dry distillation.
c) Catalytic hydration – oxidation – neutralization – dry distillation.
d) Dropping water – hydrogenation – oxidation – neutralization – dry distillation.

Aromatic benzene
IUPAC and isomers
38- Name the following according to the IUPAC system:

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 10

 Chemical reactions
39- All the following reactions produce aromatic benzene except ...............
a) hydrogenation of hexene then catalytic reforming.
b) alkaline hydrolysis of chlorobenzene then reduction.
c) hydration of calcium carbide then polymerization.
d) hydrogenation of heptene then catalytic reforming.

40- 0.25 mole of aromatic benzene reacts with 1 mole of hydrogen gas under
pressure and heat in the presence of catalyst so, at the end of reaction .............
are found in the medium.
a) saturated cyclic hydrocarbon is formed and 0.25 mole of hydrogen gas remained.
b) unsaturated cyclic hydrocarbon is formed and 0.25 mole of hydrogen gas remained.
c) saturated cyclic hydrocarbon is formed and 0.25 mole of benzene remained.
d) saturated cyclic hydrocarbon is formed only.

41- At STP, 2.24L of hydrogen gas is added to 1.28gm of naphthalene under

pressure and heat in the presence of catalyst so, at the end of reaction .........
(C=12, H=1)
a) 0.01 mole of saturated aliphatic compound is formed and 0.05 mole of H2 unreacted.
b) 0.01 mole of saturated aliphatic compound is formed and 0.05 mole of naphthalene
unreacted.
c) 0.05 mole of unsaturated aliphatic compound is formed.
d) 0.05 mole of saturated aliphatic compound is formed and 0.05 mole of naphthalene.

Conversions

42- To obtain cycloalkane from calcium carbide, we will make which of the
following steps?
a) hydrogenation – polymerization – reaction with water.
b) reaction with water – hydrogenation – polymerization.
c) hydrogenation – reaction with water – polymerization.
d) reaction with water – polymerization – hydrogenation.

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 11

43- 1 – phenyl propane is obtained by all the following methods except ...............
a) catalytic reforming of n – nonane
b) alkylation of benzene with n – propyl chloride
c) alkylation of benzene with 1 – bromo propane
d) alkylation of benzene with isopropyl chloride

44- How can you arrange the following steps to obtain a meta chloro nitro
benzene from phenol?
a) Halogenation – reduction – nitration
b) Reduction – nitration – alkylation
c) Reduction – nitration – halogenation
d) Nitration – reduction – chlorination
45- Study the following diagram then choose the correct answer:

A 𝐓𝐡𝐞𝐫𝐦𝐚𝐥
→
𝐜𝐚𝐭𝐚𝐥𝐲𝐭𝐢𝐜 𝐜𝐫𝐚𝐜𝐤𝐢𝐧𝐠 B +
𝐂𝐚𝐭𝐚𝐥𝐲𝐭𝐢𝐜 𝐫𝐞𝐟𝐨𝐫𝐦𝐢𝐧𝐠
→ C +
4H2

By knowing that the molar mass of alkane (A) = 128gm/mole. What is compound
C? (C=12, H=1)
a) Benzene
b) Toluene
c) Ethyl benzene
d) Cyclohexane

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 12

 Alcohols

IUPAC names
46- Name the following alcohols using the IUPAC system with
classification:
1- 2-
CH2CH3 CH3
CH3 – CH2 – CH – CH2 – CH2OH CH3 – CH2 – C – CH2 – CH3
OH

3- 4-
CH3
CH3 – CH – CH – CH3
CH3 – C – CH2 – CH – CH3
OH Cl
CH3 OH

5- 6-
CH3
CH2 – CH2 – CH – CH2 – CH2
CH3 – CH – CH – C – CH3
CH3 OH CH3
CH3 OH CH3

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 13

 7- 8-
C4H9
CH3 – CH2 – C – OH CH2 – CH – CH2
CH3 OH OH OH

9- 10-
CH2 – CH2 (CH3)2CHCH(CH3)OH
OH OH

Isomers and structures

47- The molecular formula C4H10O may represent the following types of alcohols
a) primary alcohols only.
b) primary and secondary alcohols only.
c) secondary and tertiary alcohols only.
d) primary, secondary and tertiary alcohols.

48- On alkaline hydrolysis of the compound C3H7Br which doesn’t contain

methylene group, the produced compound is ..............
a) primary alcohol only.
b) secondary alcohol only.
c) primary or secondary alcohol.
d) primary or tertiary alcohol.

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 14

49- On alkaline hydrolysis of the compound C4H9Br which doesn’t contain
methylene group, the produced compound is ................
a) primary alcohol only.
b) secondary alcohol only.
c) primary or secondary alcohol.
d) tertiary alcohol only.

50- Alcohol with molecular formula C4H10O and has 2 methyl groups when it is
completely oxidized, it forms a compound X its aqueous solution has PH less than
7 so, the compound X is ..............
a) 2 – methyl butanoic acid.
b) 2 – methyl propanoic acid.
c) 3 – methyl propanoic acid.
d) 3 – methyl butanoic acid.

51- The alcohol C4H10O which contains 3 methyl groups reacts with concentrated
strong mineral acid to give ................
a) symmetric alkene – 2 – methyl propene
b) symmetric alkene – 2 – butene
c) asymmetric alkene – 1 – butane
d) asymmetric alkene – 2 – methyl propene

Chemical reactions
52- Alkaline hydrolysis of primary alkyl halide produces compound A and of
secondary alkyl halide produces compound B. So, A and B are ...............
a) A is 2 – butanol, B is isobutyl alcohol.
b) A is 1 – butanol, B is 2 – methyl – 2 – propanol.
c) A is 2 – methyl – 1 – propanol, B is 2 – butanol.
d) A is 2 – methyl – 1 – propanol, B is 2 – butanol.
53- The alcohol which can’t be prepared directly by catalytic hydration of alkene
is .............
a) isopropyl alcohol
b) the isomer of dimethyl ether
c) the product of reduction of propanone
d) the product of hydrolysis of potassium methoxide

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 15

54- The hydrocarbon aliphatic derivative which contains the group (>CH – OH),
reacts with concentrated strong mineral acid to prepare asymmetric alkene so,
the alkene is ............
a) ethene
b) 2 – butene
c) propene
d) 2 – methyl propene

55- Study the following scheme then choose the correct answer which represents
Z:
𝐂𝐨𝐧𝐜.𝐇𝟐 𝐒𝐎𝟒 𝐁𝐫𝟐 /𝐂𝐂𝐥𝟒 + 𝐊𝐎𝐇 ∆
C3H7OH → (X) → (Y) → (Z)
a) CH3CHOHCH3
b) CH2OHCH2CH3
c) CH3CHOHCH2OH
d) CH3CH2CHO
Conversions
56- To convert alcohol C2H6O into alcohol C2H6O2, which of the following steps
are required?
a) Oxidation – catalytic dehydration
b) Catalytic dehydration – oxidation
c) Oxidation – catalytic hydration
d) Catalytic hydration

57- To obtain 2 – chloro propane from 1 – chloro propane, ...............

a) hydrolysis – elimination of water – reaction with hydrogen chloride
b) hydrolysis – reaction with hydrogen chloride
c) hydrolysis – elimination with water – reaction with chlorine gas in carbon tetra chloride
d) hydrolysis – complete oxidation – neutralization – dry distillation – halogenation by
substitution

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 16

58- By using the following diagram:
𝐀𝐥𝐤𝐚𝐥𝐢𝐧𝐞 𝐡𝐲𝐝𝐫𝐨𝐥𝐲𝐬𝐢𝐬 B 𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧 C
A → →
Where 1 mole of compound B contains 12 moles of atoms, the compounds A, B,
and C are ...............
a) A is 2 – bromo propane, B isopropyl alcohol, and C propanoic acid
b) A is 2 – bromo propane, B isopropyl alcohol, and C acetone
c) A is ethyl chloride, B ethyl alcohol, and C acetic acid
d) A is ethyl chloride, B ethyl alcohol, and C acetaldehyde

59- From the following diagram:

3 – chloro – 1 - propyne 𝐇𝐲𝐝𝐫𝐨𝐠𝐞𝐧𝐚𝐭𝐢𝐨𝐧 X 𝐀𝐥𝐤𝐚𝐥𝐢𝐧𝐞 𝐡𝐲𝐝𝐫𝐨𝐥𝐲𝐬𝐢𝐬 Y

→ →
Which of the following represents compounds X and Y?
Choices Compound X Compound Y
A Has 3 isomers Has 2 isomers
B 3 – chloro propane Propyl alcohol
C Prepared by reaction of propane with chlorine Can be oxidized
D Prepared from adding HCl to propene Can’t be oxidized

Phenols
60- By adding iron III chloride, 2 hydroxy organic compounds A and B separately,
a violet color is produced in case of compound A and in compound B, there is no
change, which of the following statements is correct about energy of bonds?
a) O – H for compound A is larger than O – H for compound B.
b) O – H for compound A is smaller than O – H for compound B.
c) C – O for compound B is larger than C – O for compound B.
d) C – O for compound B is equal to C – O for compound A.
61- A, B, and C are 3 compounds: on adding A to the compound C, a food flavor is
produced, and on adding sodium hydroxide to B or C, a reaction occurs while on
adding it to A, no reaction occurs, then the 3 compounds are ...............
a) A: acid, B: phenol, and C: alcohol
b) A: alcohol, B: acid, and C: phenol
c) A: acid, B: alcohol, and C: phenol
d) A: alcohol, B: phenol, and C: acid
DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 17
62- Arrange the following substances according to the PH value of their aqueous
solution. (Ethyl alcohol, sodium phenoxide, phenol)
a) Ethyl alcohol > sodium phenoxide > phenol
b) Ethyl alcohol > phenol > sodium phenoxide
c) Sodium phenoxide > phenol > ethyl alcohol
d) Sodium phenoxide > ethyl alcohol > phenol

63- If you have 3 compounds A, B, and C then adding an amount of bromine water
to each of them separately and the following notes are collected:
A ⟶ Red color is removed B ⟶ a white ppt is formed C ⟶ Red color remained
Which of the following choices represents those compounds?
Choices A B C
A C2H4 C2H5OH C2H6
B C6H5OH C2H4 C2H2
C C2H4 C6H5OH C2H6
D C2H6 C2H4 C6H5OH

64- Study the following diagram then choose the correct answer:
𝟐𝐍𝐚 𝟖𝟎𝟎℃+ 𝐅𝐞𝟐 𝐎𝟑 B 𝐂𝐥𝟐 ∆ C
2C2H5OH → 2C2H5ONa + A → →

Choices Substance B Substance C Substance D color Substance E Substance F

A Fe FeCl2 Reddish – brown Violet ppt Violet ppt
B Fe FeCl3 Bloody red Pale blue ppt Pale blue ppt
C Fe FeCl3 Violet Reddish – brown Bloody red
ppt
D FeO FeCl2 Violet Reddish – brown Reddish – brown
ppt ppt

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 18

65- How can you obtain phenol from aliphatic open chain hydrocarbon?
a) Catalytic reforming – chlorination – alkaline hydrolysis
b) Chlorination – catalytic reforming – alkaline hydrolysis
c) Alkaline hydrolysis – chlorination – catalytic reforming
d) Catalytic reforming – alkaline hydrolysis – chlorination
Carboxylic acids

Acid ⟶ HCOO – or - COOH or – CO2H

IUPAC names
66- Give the IUPAC names for the following compounds:
CH3 – CH2 – CH – CH – COOH
Cl Cl

67- The general formula of unsaturated aliphatic carboxylic acid to be converted

into saturated acid, it required 2 moles of hydrogen gas is ...............
a) CnH2n + 1COOH
b) CnH2nCOOH
c) CnH2n – 3COOH
d) CnH2n – 1COOH

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 19

Chemical reactions
68- Complete the following table:
Ethanol Phenol Acetic acid
1- Na

2- NaOH

3- Na2CO3

4- HCl

69- 1 mole of the following compound can react with

............... mole(s) of sodium metal Na
............... mole(s) of sodium hydroxide NaOH
............... mole(s) of sodium bicarbonate
............... mole(s) of hydrogen chloride HCl

70- Oxidation of the following compound gives

...............
a) 2,3 – dimethyl propanoic acid
b) 2,3 – dimethyl butanoic acid
c) 2,3 – diethyl butanoic acid
d) 2,4 – diethyl propanoic acid

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 20

 Conversions

71- The correct set of processes to get meta – chloro benzoic acid from ethyne is
...............
a) polymerization ⟶ oxidation ⟶ halogenation ⟶ alkylation
b) polymerization ⟶ alkylation ⟶ oxidation ⟶ halogenation
c) alkylation ⟶ polymerization ⟶ halogenation ⟶ oxidation
d) oxidation ⟶ polymerization ⟶ halogenation ⟶ alkylation

72- To get the simplest aromatic compound from aromatic compound, its
molecular formula C7H8, which of the following arrangements are correct?
a) Neutralization – oxidation – dry distillation
b) Oxidation – dry distillation – neutralization
c) Neutralization – dry distillation – oxidation
d) Oxidation – neutralization – dry distillation

73- For 2 – hydroxy propanoic acid, all the following are correct except ...............
a) 1 mole of it reacts with 2 moles of NaOH forming a sodium salt + 2 moles of water.
b) its boiling point is higher than propanoic acid.
c) convert chromic acid into green color.
d) can be reduced into glycol.

74- The correct steps to obtain benzoic acid from acetic acid are ..............
a) oxidation – neutralization – dry distillation – halogenation – alkylation.
b) neutralization – dry distillation – halogenation – alkylation – oxidation.
c) neutralization – dry distillation – alkylation – oxidation.
d) neutralization – dry distillation – halogenation – alkylation.

75- 2 compounds: A and B both are from hydrocarbon derivatives, A is produced

from oxidation of B so, A and B are ..................
a) A: benzoic acid, B: toluene
b) A: ethylene glycol, B: ethene
c) A: CH3CH(OH)CH3, B: CH3COCH3
d) A: Oxalic acid, B: ethylene glycol
DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 21
 Esters

Ester ⟶ - OOC – or - COO – or – CO2 -

IUPAC names and isomers

76- Give the IUPAC names for the following compounds:

O O
║ ║
CH3 – CH2CH2 – C – O – CH3 C6H5 – C – O – CH2CH3

O O
║ ║
CH3 – CH2 – C – O – C6H5 CH3 – CH2CH2 – O – C – CH3

77- Which of the following represents the isomer of ethyl pentanoate?

a) Pentyl formate
b) Propyl butanoate
c) Phenyl benzoate
d) Phenyl acetate

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 22

78- Study the following table then choose the correct answer:
A An isomer of propanoic acid has lower boiling point than it.
B An isomer of ethyl ethanoate has higher boiling point than it.

a) Compound B is propanoic acid and A is propyl formate

b) Compound B is butanoic acid and A is ethyl formate
c) Compound A is ethyl formate and B is butanoic acid
d) Compound A is methyl ethanoate and B is propanoic acid

Chemical reactions
79- The ester that is produced from acetic acid + carbolic acid is ..............
a) C6H5COOCH3
b) CH3COOC2H5
c) CH3COOC6H5
d) CH3CH2COOC6H5

80- To get HCOO(CH2)3CH3, ...............

a) esterification of formic acid with n – propyl alcohol
b) esterification of methanol with 3 – methyl propanoic acid
c) esterification of formic acid with n – butyl alcohol
d) esterification of butanoic acid with methanol

81- A compound C7H6O2 doesn’t react with sodium carbonate and its boiling point
is low is .............
a) benzoic acid
b) phenyl formate
c) methyl benzoate
d) phenyl acetate

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 23

82- When 1 mole from ethylene glycol reacts with 2 moles of acetic acid, the
product will be ...............

b) CH2COOCH3
CH2COOCH3
c) CH3COOC2H5
d) CH3COO(CH2)2CH3

83- Acidic hydrolysis of ester C2H4O2 gives 2 compounds A and B where boiling
point of B is higher than A, what is the chemical formula of B?
a) HCOOH
b) CH3OH
c) CH3COOH
d) CH3CH2OH

84- Which of the following has the highest boiling point alcohol and produced
from alkaline hydrolysis of isomers C6H12O2?
a) C6H13OH
b) C2H5OH
c) CH3OH
d) C4H9OH

85- Which of the following compounds produces sodium benzoate from

hydrolysis in basic medium?
a) HCOOC6H5
b) C6H5COOCH3
c) C6H5OOCCH3
d) CH3COOCH2C6H5

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 24

86- What is the ester which gives A and B by saponification (alkaline hydrolysis)?
A B
Salt of monobasic carboxylic acid, 1 Alcohol C3H8O is completely oxidized
mole of it contains 2 moles of carbon by acidified KMnO4 to C3H6O.
atoms.
a) n – propyl ethanoate
b) ethyl propanoate
c) propyl propanoate
d) isopropyl ethanoate

87- One of the products of the ammonolysis of the ester C8H8O2 gives benzamide,
what is the IUPAC name of this ester?
a) benzoate
b) phenyl acetate
c) ethyl benzoate
d) phenyl formate

88- What is the ester which gives A and B by ammonolysis?

A B
C3H7CONH2 Primary alcohol C3H8O

a) propyl butanoate
b) butyl propanoate
c) propyl propanoate
d) butyl butanoate
89- All the following reactions give benzoic acid except ...............
a) catalytic reforming of heptane then oxidation.
b) alkylation of benzene then oxidation.
c) acidic hydrolysis of ethyl benzoate.
d) acidic hydrolysis of phenyl methanoate.

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 25

90- The correct arrangement of the written compounds according to their boiling
points is ............ (Propanoic acid – Methyl acetate – Propanol)
a) propanol > methyl acetate > propanoic acid
b) propanoic acid > propanol > methyl acetate
c) methyl acetate > propanol > propanoic acid
d) methyl acetate > propanoic acid > propanol

91- 2 isomers A and B of molecular formula that each mole contains number of
carbon atoms = 8 × Avogadro’s number and each molecule contains 8 hydrogen
atoms and 2 oxygen atoms, as NaHCO3 makes effervescence with isomer A but not
with B so, we can obtain the simplest aromatic hydrocarbon through 2 steps:
a) from A only
b) from B only
c) from both A and B
d) neither from A nor B

92- The correct steps to obtain acetamide from ethane are ..............
a) halogenation – hydrolysis – esterification – ammonolysis.
b) halogenation – hydrolysis – complete oxidation – esterification – ammonolysis.
c) hydration – complete oxidation – esterification – ammonolysis.
d) halogenation – hydrolysis – complete oxidation – neutralization with ammonia solution.

93- From the following diagram:

All the following are correct except ..............

a) compound A is methyl benzoate
b) compound B dissolves in water
c) compound C reacts by substitution and addition
d) compound D has the general formula CnH2n + 2

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 26

94- In the following table 4 hydrocarbon derivatives:
Hydrocarbon Information about the compound
derivatives
A It is an isomer of compound D
B Acid has 12gm of carbon in 1 mole of it
C An alcohol causes blindness and madness
D Is produced from reaction between C and B

Which of the following figures expresses the boiling point gradient of the 4
compounds?

a) A
b) B
c) C
d) D

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 27

95- The following table describes the radicals which esterical isomers of butanoic
acid is derived from:
Isomers R – of acid R – of alcohol
Isomer (1) It doesn’t contain R group Its molar mass is 43gm/mole

Isomer (2) R is less than R of alcohol by CH2 - C2H5

Alkaline hydrolysis of isomer (1) gives ..............

a) methanol and sodium propanoate
b) ethanol and sodium acetate
c) sodium ethanoate and methanol
d) propanol and sodium methanoate

96- The substance that forms isomer (2) by losing OH group is ............. and it can
be obtained again by ............. of the same ester.
a) methanol / hydrolysis in acidic medium
b) ethanoic / hydrolysis in acidic medium
c) propanoic / ammonia decomposition
d) ethanol / alkaline hydrolysis

97-

Which of the following choices is correct?

Choices A X W Y
A C2H5COOCH3 C2H5OH C2H5CONH2 H2O + H+
B CH3COOCH3 C2H5OH C2H5CONH2 H2O + H+
C CH3COOC2H5 C2H5OH CH3CONH2 H2O + H+
D CH3COOC2H5 C2H5OH C2H5CONH2 H2O + H+
DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 28
98- The following diagram represents hydrogen exponent PH of some organic
compound solution (have equal concentration) so, the correct choice is ...............
Organic A B C D
compound
A Benzoic acid Carbolic Acetic acid Ethanol
acid
B Carbolic acid Ethanol Acetic acid Benzoic
acid
C Ethanol Carbolic Acetic acid Benzoic
acid acid
D Benzoic acid Acetic Carbolic Ethanol
acid acid

99- Organic compound (A) has a molecular formula C3H8O, hot concentrated
sulphuric acid is added to it at 1800C then compound B is produced which
removes the red color of bromine water, by oxidation of compound A that
produces compound C which is oxidized again to produce compound D which
turns litmus paper into red, then by reacting compound D with compound A,
compound E is produced which has characteristic odor. Which of the following
choices is correct?
Choices A B C D E
A CH3CH2CH2OH CH3CHCH2 CH3COCH3 C2H5COOH CH3CH2COOC3H7
B CH3CHOHCH3 CH3CHCH2 CH3COCH3 C2H5COOH CH3CH2COOC3H7
C CH3CH2CH2OH CH3CHCH2 CH3CH2CHO C2H5COOH CH3CH2COOC3H7
D CH3CHOHCH3 CH3CHCH2 CH3CH2CHO C2H5COOH C2H5COOCH(CH3)2

Dacron fibers
100- When organic compound A reacts with organic compound B, they produce a
compound which has an effective role in treating heart diseases so, A and B are
...............
a) A: terphethalic acid, B: ethylene glycol.
b) A: phenol, B: formaldehyde.
c) A: phenol, B: ethylene glycol.
d) A: glycerol, B: sulphuric acid.

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 29

101- After ............. for both compounds ethene and 1,4 – dimethyl benzene, their
products can react with each other.
a) hydrogenation
b) hydration
c) oxidation
d) polymerization

Aspirin and Marookh Oil

102- We can get sodium methoxide from the following compound by ...............
a) hydrolysis – neutralization
b) hydrolysis – oxidation – reaction with caustic soda
c) hydrolysis in the acidic medium – reaction with sodium
d) reaction with NaOH

103- Which of the following is incorrect about the produced inorganic compound
from dry distillation of sodium benzoate?
a) Is used to differentiate between phenol and benzoic acid
b) Its hydroxyl exponent is less than 7
c) Is used to differentiate between ethanol and glycine
d) Is used to differentiate between salicylic acid and aspirin

Diagram questions
104- Study the following diagram knowing that the molecular formula of
compound D is C8H8O2:

A 𝐂𝐚𝐭𝐚𝐥𝐲𝐭𝐢𝐜 𝐫𝐞𝐟𝐨𝐫𝐦𝐢𝐧𝐠 𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧 𝐑𝐎𝐇 D

→ B → C →
a) A is octane and ammonolysis of D gives phenol and acetamide
b) A is octane and ammonolysis of D gives phenol and acetamide
c) A is heptane and ammonolysis of D gives benzamide and ethanol
d) A is heptane and ammonolysis of D gives benzamide and methanol

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 30

105- Study the following diagram and then answer the following question:
Know that 1 mole of monohydric alcohol X contains 3 moles of carbon atoms.
𝐜𝐨𝐧𝐜.𝐇𝟐 𝐒𝐎𝟒 /𝟏𝟖𝟎℃ 𝐊𝐌𝐧𝐎𝟒 /𝐚𝐥𝐤
X→ Y → Z
a) X is tertiary alcohol and Z is 1,2 – dihydroxy propane
b) X is secondary alcohol and Z is 1,2 – dihydroxy propane
c) X is primary alcohol and Z is 2,3 – dihydroxy propane
d) X is tertiary alcohol and Z is 2,3 – dihydroxy propane

106- Study the following diagram and answer the following question:
Knowing that A and C are isomers of C3H8O and D doesn’t react with Na2CO3. What
are A – B – C – D?
𝐃𝐞𝐡𝐲𝐝𝐫𝐚𝐭𝐢𝐨𝐧 𝐂𝐚𝐭𝐚𝐥𝐲𝐭𝐢𝐜 𝐡𝐲𝐝𝐫𝐚𝐭𝐢𝐨𝐧 𝐂𝐨𝐦𝐩𝐥𝐞𝐭𝐞 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
A→ B→ C → D

107- Study the following diagram:

Knowing that B is monobasic aliphatic acid, 1 mole of it contains 3 moles of
carbon atoms. What are A/B/C/X and 1?
𝐀𝐦𝐦𝐨𝐧𝐨𝐥𝐲𝐬𝐢𝐬
Propene + H2O A (B) C → X+A
H2SO4 (1)

108- Study the following diagram:

C4H8 is an open – chain branched hydrocarbon. What are A and B?
C4H8 H2O A HCl B
H2SO4 ZnCl2

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 31

109- Study the following diagram where the general formula of A is
CnH2n +1X and C reacts with sodium carbonate. What are these symbols?

(𝟏) (𝟐) (𝟑) (𝟒)/𝑪𝟐 𝑯𝟓 𝑶𝑯

CH4 → A → B → C→ D

110- The following compound is produced from ............... by ................

a) ethyl butanoate – hydrolysis in basic medium
b) methyl pentanoate – ammonolysis
c) propyl butanoate – hydrolysis in the acidic medium
d) ethyl butanoate – ammonolysis

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 32

 Model Answ er of Exam Night Rev ision
Chapt er 5 Organic Chemist ry
Question Number Model Answer
1. Essay Question
2. A
3. A
4. B
5. B
6. C
7. D
8. D
9. A
10. C
11. C
12. Essay Question
13. D
14. A
15. B
16. C
17. A
18. C
19. C
20. C
21. A
22. C
23. D
24. C
25. B
26. B
27. B
28. D
DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 33
 29. D
30. C
31. C
32. B
33. A
34. D
35. A
36. C
37. B
38. Essay Question
39. D
40. A
41. A
42. D
43. D
44. C
45. B
46. Essay Question
47. D
48. B
49. D
50. B
51. D
52. D
53. D
54. C
55. C
56. B
57. A
58. B
59. C
60. B

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 34

 61. D
62. D
63. C
64. C
65. A
66. Essay Question
67. C
68. Essay Question
69. Essay Question
70. B
71. B
72. D
73. A
74. B
75. D
76. Essay Question
77. B
78. B
79. C
80. C
81. B
82. A
83. A
84. D
85. B
86. D
87. A
88. A
89. D
90. B
91. B
92. B

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 35

 93. D
94. Essay Question and Choice is
C
95. D
96. B
97. C
98. B
99. C
100. A
101. C
102. C
103. D
104. D
105. B
106. Essay Question
107. Essay Question
108. Essay Question
109. Essay Question
110. D

1- Name the following according to the IUPAC system:

CH3 – CH – CH3 CH3 – (CH2)3 – CH2 – C(CH3)3

C3H7

2- methyl Pentane 2,2-dimethyl heptane

Cl Br NO2 CH3 – CH = CH – CH2 – CH2Cl

CH3 – CH – CH – CH2 – CH – CH3

3-bromo-2-Chloro-5-nitro hexane 5-Chloro-2-pentene

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 36

 C2H5 Br

CH3 – CH – CH2 – C  CH CH3 – CH2 – C – C  CH

CH2 – CH2 – CH3

4-methyl-1-hexyne 3-bromo-3-ethyl-1-hexyne

Br – CH2 – CH = CH – CH2Cl CH3 – CH – CH2 – CH2

C6H13 C6H5

1-bromo-4-Chloro -2-butene 3-methyl-1-phenyl nonane

12-Hydrocarbon molecule contains number of carbon atoms = (n) so,

complete burning of 1 mole of it produces ………. moles CO2 and ……….
moles of H2O.
For alkane CnH2n+2 + O2 gives by heating n CO2 + n+1 H2O
For alkene CnH2n + O2 gives by heating n CO2 and n H2O
For alkyne Cn H2n-2 + O2 gives by heating nCO2 and n-1 H2O
38- Name the following according to the IUPAC system:

4-bromo-1,2-dichloro benzene 4-bromo-1-Chloro-2-nitro

benzene

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 37

 2-bromo-1-Chloro-3-nitro
1-bromo-3-Chloro-5-nitro benzene benzene

46- Name the following alcohols using the IUPAC system with
classification:
1- 2-
CH2CH3 CH3
CH3 – CH2 – CH – CH2 – CH2OH CH3 – CH2 – C – CH2 – CH3
OH

Primary monohydric Tertiary Monohydric

3-ethyl-1-pentanol 3-methyl-3-pentanol

3- 4-
CH3
CH3 – CH – CH – CH3
CH3 – C – CH2 – CH – CH3
OH Cl
CH3 OH

Secondary Monohydric
Secondary Monohydric
3-Chloro-2-butanol
4,4-dimethyl-2-pentanol

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 38

5- 6-
CH3
CH2 – CH2 – CH – CH2 – CH2
CH3 – CH – CH – C – CH3
CH3 OH CH3
CH3 OH CH3

Secondary Monohydric Secondary Monohydric

2,2,4-trimethyl -3-pentanol 4-heptanol

7- 8-
C4H9
CH3 – CH2 – C – OH CH2 – CH – CH2
CH3 OH OH OH

Tertiary Monohydric Trihydric Alcohol

3-methyl-3-heptanol 1,2,3-trihydroxy propane

9- 10-
CH2 – CH2 (CH3)2CHCH(CH3)OH
OH OH

Dihydric Alcohol Secondary Monohydric

1,2-dihydroxy ethane 3-methyl-2-butanol

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 39

66- Give the IUPAC names for the following compounds:
CH3 – CH2 – CH – CH – COOH
Cl Cl

2,3-dichloro pentanoic acid 3-methyl butanoic acid

2,4-dichloro benzoic acid 3-bromo-5-floro benzoic acid

68- Complete the following table:

Ethanol Phenol Acetic acid
1- Na Reacts Reacts Reacts

2- NaOH Doesn’t react Reacts Reacts

3- Na2CO3 Doesn’t reacts Doesn’t reacts Reacts

4- HCl Reacts Doesn’t reacts Doesn’t reacts

69- 1 mole of the following compound can react with

........3....... mole(s) of sodium metal Na
........2....... mole(s) of sodium hydroxide NaOH
........1....... mole(s) of sodium bicarbonate
.........1...... mole(s) of hydrogen chloride HCl

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 40

76- Give the IUPAC names for the following compounds:

O O
║ ║
CH3 – CH2CH2 – C – O – CH3 C6H5 – C – O – CH2CH3

Methyl butanoate Ethyl Benzoate

O O
║ ║
CH3 – CH2 – C – O – C6H5 CH3 – CH2CH2 – O – C – CH3

Phenyl Propanoate Propyl ethanoate

94- In the following table 4 hydrocarbon derivatives:

Hydrocarbon derivatives Information about the compound

A It is an isomer of compound D
CH3 COOCH3
C2H5COOH
B Acid has 12gm of carbon in 1 mole of it
Cn H2n O2
CH2O2 ( HCOOH)
C An alcohol causes blindness and madness

C2H5OH
D Is produced from reaction between C and B

HCOOC2H5

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 41

106- Study the following diagram and answer the following question:
Knowing that A and C are isomers of C3H8O and D doesn’t react with Na2CO3. What
are A – B – C – D?
𝐃𝐞𝐡𝐲𝐝𝐫𝐚𝐭𝐢𝐨𝐧 𝐂𝐚𝐭𝐚𝐥𝐲𝐭𝐢𝐜 𝐡𝐲𝐝𝐫𝐚𝐭𝐢𝐨𝐧 𝐂𝐨𝐦𝐩𝐥𝐞𝐭𝐞 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
A→ B→ C → D
A = 1-propanol
B = Propene
C = 2-propanol
D = Acetone

107- Study the following diagram:

Knowing that B is monobasic aliphatic acid, 1 mole of it contains 3 moles of
carbon atoms. What are A/B/C/X and 1?
𝐀𝐦𝐦𝐨𝐧𝐨𝐥𝐲𝐬𝐢𝐬
Propene + H2O A (B) C → X+A
H2SO4 (1)
A= 2-propanol
B = Propanoic acid
C = Isopropyl propanoate
X = C2H5CO-NH2 Propanamide

108- Study the following diagram:

C4H8 is an open – chain branched hydrocarbon. What are A and B?
C4H8 H2O A HCl B
A= 2-methyl Propene
B= 2-methyl-2-propanol
C= 2-Chloro-2-methyl propane

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 42

109- Study the following diagram where the general formula of A is
CnH2n +1X and C reacts with sodium carbonate. What are these symbols?

(𝟏) (𝟐) (𝟑) (𝟒)/𝑪𝟐 𝑯𝟓 𝑶𝑯

CH4 → A → B → C→ D
A= CH3Cl
B= CH3OH
C= HCOOH
D= HCOOC2H5

DR. JOSEPH ADEL CHAPTER 5 EXAM NIGHTS 43