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Organic Chemistry Testbank Dr. Baya education G11, G12
Organic Chemistry Testbank Dr. Baya education G11, G12
Table of contents
- Part 1(Zumdahl)
- Part 6 (Olympics)
Page 2 of 209
Part.1 (Zumdahl Qs)
1.Name the following:
A) Isopropane
B) Methylpentane
C) Methylbutane
D) n-pentane
A) n-heptane
B) 2-methyl-2-ethylbutane
C) 3,3-dimethylpentane
D) 2,2-diethylpropane
A) Ethane
B) Propane
C) Butane
D) Pentane
Page 3 of 209
A) 2,4-diethylpentane
B) 3,5-dimethylheptane
C) secondary ethylpentane
D) 2,3-dimethyl-2,3-diethylpropane
A) Pentane
B) Hexane
C) Heptane
D) Octane
However, the teacher pointed out that, although the molecule could be correctly
drawn from this name, the name violates the IUPAC rules. What is the correct
(IUPAC) name of the molecule?
A) 2-t-butyl-4-methylpentane
B) 2,2,3,5-tetramethylhexane
C) 2,4,5,5-tetramethylhexane
D) 1-sec-butyl-1,2,2-trimethylpentane
Page 4 of 209
A) 3-methyl-4-isopropylpentane
B) 2-ethyl-4-tertiary-butylpentane
C) 2,2,3,5-tetramethylheptane
D) t-butylethane
8. What is the compound whose carbon skeleton (minus any hydrogen atoms) appears
below?
A) 2,4-diethyl-3,6-dimethylheptane
B) 2,5-dimethyl-4,6-diethylheptane
C) 1,4-diethyl-3,6-dimethyl-tridecane
D) 5-ethyl-3,6-trimethyloctane
E) 4-ethyl-2,5,6-trimethyloctane
10. The compound below is the carbon skeleton (minus any hydrogen atoms) of
Page 5 of 209
Which of these phrases could be used to describe this compound?
I. C12H26
II. a substituted octane
III. a compound with 3 tertiary carbons
IV. a compound with 3 secondary carbons
V. a compound with 2 isopropyl groups
A) I, II, III
B) II, III, IV
C) III, IV, V
D) II, IV, V
A) ethane – C2H4
B) pentane – C5H12
C) hexane – C6H14
D) heptane – C7H16
12.Why does octane have a higher boiling point than ethane, 126°C versus –89°C?
A) Octane exhibits hydrogen bonding and ethane does not.
B) Octane has a higher vapor pressure than ethane.
C) Octane contains more double bonds than ethane.
D) Octane has stronger London dispersion forces than ethane.
Page 6 of 209
14. Which is a possible product of the chlorination of butane in the presence of
light?
A) C4H9Cl
B) C4H8Cl
C) C4H10Cl2
D) C4H6Cl2
15. Which of the following, upon reacting with oxygen, would form the greatest
amount of carbon dioxide?
A) n-pentane
B) isopentane
C) neopentane
D) Two of the above would form equal amounts.
E) All (A-C) of the above would form equal amounts.
A) 1-hexyne
B) 2-ethynyl butane
C) 2-ethyl-3-butyne
D) 3-methyl-1-pentyne
A) 1,1,1-trichloro-5-bromo-3-pentene
B) 1-bromo-5,5,5-trichloro-2-pentene
C) 1,1,1-trichloro-5-bromo-2-pentene
D) 1,1,1-trichloro-5-bromo-3-pentyne
Page 7 of 209
18. CH3C CCH2CH2Cl is named:
A) 1-chloro-3-pentyne
B) 5-chloro-2-pentene
C) 1-acetylenyl-3-chloropropane
D) 5-chloro-2-pentyne
A) I and II
B) I and III
C) II and III
D) III and IV
24. Chemical reactions involving alkanes in which hydrogen atoms are removed
and the product is an unsaturated hydrocarbon are called
A) combustion reactions
B) dehydrogenation reactions
C) substitution reactions
D) addition reactions
A) 2-chloro-3-chloro-cis-2-butene
B) 2,3-dichloro-cis-2-butene
C) 2,3-dichloro-trans-2-butene
D) 1-chloro-1-methyl-2-chloro-propene
Page 9 of 209
26.Which of the following compounds can exhibit geometrical isomerism?
A)
B)
C)
D)
E)
28.How many geometric isomers can be drawn for the following compound:
CH3CH=CHCH2CH=C(CH3)2
A) 2
B) 3
C) 4
D) 5
Page 10 of 209
29. What is the compound represented by the following structure?
A) cyclohexene, C6H10
B) cyclohexane, C6H12
C) cyclohexatriene, C6H9
D) cyclohexatriene, C6H12
E) benzene, C6H6
A) 2
B) 3
C) 4
D) 5
A) oxidation
B) reduction
C) substitution
D) addition
A) naphthalene
B) benzene
C) anthracene
D) phenanthrene
E) toluene
Page 11 of 209
A) methanol
B) ethanol
C) propanol
D) isopropanol
37. The boiling point of methanol is much higher than that of ethane. This is
primarily due to :
Page 12 of 209
38.Classify the following molecule:
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) ether
40. When C4H8 is treated with water and H2SO4, a tertiary alcohol is produced.
Which of the following structures could represent C4H8 in this reaction?
A) CH3CH=CHCH3
B) CH3CH2CH=CH2
C)
D) CH3CH2CH2CH3
42. When the following organic compound is oxidized, what is the major organic
product?
Page 13 of 209
A) 3-pentanoic acid
B) 3-pentanol
C) 3-pentanone
D) 3-pentanal
A) acetone
B) butyraldehyde
C) diethylketone
D) diethyl ether
44. Identify the functional group present in the following organic compound:
A) ester
B) aldehyde
C) ether
D) ketone
Page 14 of 209
A) 2-chloro-3-ethyl-1-isopropylbutanone
B) isopropyl-chloro,methylbutyl ketone
C) 2-butyl,chloro,isobutanoyl methane
D) 4-chloro-2,5-dimethyl-3-heptanone
A) aldehyde
B) ester
C) amine
D) alcohol
E) none of these
A)
B) CH3CH2OCH3
C)
D) CH3CH2NH2
Page 15 of 209
A) acid
B) aldehyde
C) amine
D) ketone
A) acid
B) aldehyde
C) amine
D) ketone
Page 16 of 209
53.What organic molecules have the general formula RCOOH?
A) esters
B) alcohols
C) carboxylic acids
D) ketones
A) n-propyl acetate
B) isopropyl formate
C) isopropyl acetate
D) ethyl propanoate
Page 17 of 209
57.Which of the following has a double C-O bond and a single C-O bond?
A) ketone
B) ester
C) alcohol
D) amide
II.
III.
59. If you were to heat pentanoic acid and 2-butanol with a catalytic amount of
strong acid, you would most likely discover in your flask:
A) a ketone
B) an ester
C) an amine
D) an alkane
60.A carboxylic acid will react with an alcohol to form a(n) __________ and a
water molecule.
A) ester
B) amine
C) polymer
D) ketone
Page 18 of 209
A) combustion
B) hydrogenation
C) addition
D) condensation
63.H2CCHCH2N(CH3)2 is
A) primary amine
B) secondary amine
C) tertiary amine
D) amino acid
Page 19 of 209
A) CH3NH2
B) (CH3)2NH
C)
D) NH3
66.For which of the following compound(s) are cis and trans isomers possible?
A) 2,3-dimethyl-2-butene
B) 3-methyl-2-pentene
C) 4,4-dimethylcyclohexanol
D) ortho-chlorotoluene
A)
B)
C)
D)
Page 20 of 209
68.Which structure represents an optically active aldehyde?
A)
B)
C)
D)
E)
E) none of these
Page 21 of 209
70. Which of the following is optically active (i.e., chiral)?
A) HN(CH3)2
B) CH2Cl2
C) 2-chloropropane
D) 2-chlorobutane
71. Identify all the functional groups present in the following organic compound:
1) ketone, 2) aldehyde, 3) acid, 4) alcohol, 5) ether, 6) ester, 7) amine.
A) 2,6
B) 2,5
C) 1,2
D) 1,2,5
A) copolymer
B) homopolymer
C) dimer
D) two of these
A) nylon
B) PVC
C) elastomer
D) polymer
Page 22 of 209
74.Consider the polymer drawn below:
75.The polymer
is formed by addition of
A) CH2=CH-CH3
B) CH3CH2CH3
C) CH3–CH=CH–CH3
D) H2C=CH–CH=CH2
76. Which of the following pairs of substances could form an addition copolymer?
A) H2C=CHCH3 + HOCH2CH2COOH
B) HO(CH2)4COOH + HOCH2CH=CHCH3
C) H2C=CHCH + H2C=CHCH3
D) HOCH2CH2OH + HOOCCOOH
Page 23 of 209
77. The structure of the polymer used in a freezer wrap can mainly be described as
follows:
[CCl2 –CH2 –CCl2–CH2 –CCl2 –CH2 –CCl2 –CH2]n
The chief monomer of this wrap would have which structure?
A) CCl2=CH2
B) Cl2C–CH2
C) Cl2C=CH2=CCl2
D) CCl2
Page 24 of 209
81. Which of the following monomers are used to produce the polymer:
I.
II.
III.
A) I
B) II
C) III
D) I and III
I. HOCH2CH2OH
II HOOCCH2CH2COOH
III. HOCH2CH2COOH
IV. HOCH=CHOH
V. HOOCCH=CHCOOH
A) II
B) III
C) I and II
D) IV and V
E) II and III
Page 25 of 209
A) copolymer
B) homopolymer
C) dimer
D) two of these
84.In each pair below the relative strength of the polymer types is indicated with
the stronger polymer on the right. Which comparison is wrong?
85. When sulfur is added to rubber and the mixture is heated, the resulting rubber
is still elastic but much stronger. This process is called
A) addition polymerization
B) isomerization
C) oligomerization
D) vulcanization
E) halogenation
Page 26 of 209
88. HDPE, or high-density polyethylene, is a highly recyclable material because:
A) It has a high molecular weight (molar mass).
B) It is both strong and tough.
C) It is a thermoplastic polymer.
D) It is a thermoset polymer.
Page 27 of 209
Answers
1.C 2.C 3.B 4.B 5.D 6.B 7.C 8.E 9.C 10.A
11.A 12.D 13.A 14.A 15.E 16.D 17.B 18.D 19.D 20.C
21.D 22.B 23.A 24.B 25.C 26.B 27.C 28.A 29.E 30.B
31.C 32.A 33.A 34.D 35.A 36.B 37.B 38.C 39.B 40.C
41.B 42.C 43.D 44.C 45.D 46.E 47.C 48.B 49.D 50.D
51.B 52.B 53.C 54.C 55.B 56.D 57.B 58.E 59.B 60.A
61.D 62.B 63.C 64.A 65.B 66.B 67.D 68.B 69.E 70.D
71.A 72.B 73.D 74.B 75.C 76.C 77.A 78.A 79.C 80.D
81.B 82.C 83.A 84.B 85.D 86.B 87.B 88.C 89.D 90.C
Page 28 of 209
Part 2 (central science)
1) Hydrocarbons containing only single bonds between the carbon atoms are called
__________.
A) alkenes
B) alkynes
C) aromatics
D) alkanes
A) alkenes
B) alkynes
C) aromatics
D) alkanes
A) ethylene
B) ethane
C) acetylene
D) propyne
Page 29 of 209
A) ion-dipole attraction
B) dipole-dipole attraction
C) London forces
D) hydrogen bonding
A) alkanes
B) aromatic hydrocarbons
C) alkynes
D) alkenes
A) C=C bond
B) C≡C bond
C) C–C bond
D) C=H bond
A) octahedral
B) square planar
C) trigonal planar
D) tetrahedral
Page 30 of 209
8) Hybridization of the carbon atom indicated by (*) in CH3–*CH2–CH3,
*CH=CH2, and CH3–C≡CH is __________, __________, and __________,
respectively.
A) sp3, sp2, sp
A) 4
B) 6
C) 3
D) 9
A) 0
B) 1
C) 2
D) 3
Page 31 of 209
A) 2
B) 4
C) 6
D) 8
A) C2nH2n+2
B) CnH2n
C) CnH2n+2
D) CnH2n-2
A) alkyne
B) alkene
C) alkane
D) aromatic compound
Page 32 of 209
A) 2,4-methylbutene
B) 2,5-dimethylpentane
C) 2,4-ethylbutene
D) 2,4-dimethyl-1-pentene
A) 2, 3
B) 5, 12
C) 1, 5
D) 9, 15
Page 33 of 209
16) Gasoline and water do not mix because gasoline is __________.
A) water
B) NaNO3
C) HCl
D) hexane
A) methane
B) propane
C) benzene
D) heptane
Page 34 of 209
A) 0
B) 25
C) 50
D) 75
A) 2, 3, 5 - octatriene
B) 2, 5, 6 - octatriene
C) 2, 3, 6 - octatriene
D) 3, 5, 6 - octatriene
A) C3H8
B) C3H6
C) C6H6
D) C17H36
B) alkynes
C) alkanes
D) cycloalkanes
A) 1-bromobutane
B) 2-bromobutane
C) 1,2-dibromobutane
D) 2,3-dibromobutane
E) no reaction
B) 1
C) 2
D) 3
A) R–O–R'
B) R–CO–R'
C) R–CO–OH
D) R–OH
A) alkyne
B) alcohol
C) ketone
D) aldehyde
Page 37 of 209
A) R–O–R'
B) R–CO–R'
C) R–CO–OH
D) R–CHO
A) R–O–R'
B) R–CO–R'
C) R–CO–OH
D) R–H
A) alkenes
B) benzene
C) ketones
D) primary alcohols
B) amide
C) ketone
D) aldehyde
A) carboxylic acid
B) ketone
C) aldehyde
D) ester
A) sp
B) sp3
C) sp2
D) d2 sp3
Page 39 of 209
34) Optically active molecules that are mirror images of each other are called
__________.
A) allotropes
B) geometrical isomers
C) enantiomers
D) chiral compounds
A) C5H5
B) C3H6
C) C4H6
D) C2H6
36) If each of the following represents an alkane, and a carbon atom is located at
each vertex with the proper number of hydrogen atoms also bonded to it, which
one is the most reactive?
Page 40 of 209
37) How many isomers are possible for C5H12?
A) 1
B) 2
C) 3
D) 4
Page 41 of 209
39) When petroleum is distilled to separate the components by boiling point, the
component with the highest boiling point is called __________.
A) gas
B) gasoline
C) kerosene
D) paraffin
E) asphalt
40) How many structural isomers (include all types except optical) can be drawn
for C5H10?
A) 5
B) 6
C) 7
D) 11
A) none
B) 1
C) 2
D) 3
Page 42 of 209
42 ) Which statement about hydrocarbons is false?
43) Which statement about addition reactions between alkenes and HBr is false?
B) Bromine attacks the alkene carbon atom possessing a positive partial charge.
C) A hydrogen atom attaches itself to the alkene carbon atom possessing a negative
partial charge.
44) Benzene behaves differently from a hydrocarbon which simply contains three
C=C bonds in that the latter would be expected to react much more readily with
__________.
A) H2
B) Cl2
C) Br2
D) HCl
Page 43 of 209
45) During World War II, TeflonTM was used __________.
B) to form the tube to keep the separate parts of the critical mass apart until the
time for detonation of the bomb
D) as a liner inside the atomic bomb to protect the guidance system from radiation
46) Alcohols are hydrocarbon derivatives in which one or more hydrogens have
been replaced by a hydroxyl functional group. __________ is the general formula
of an alcohol.
A) R–O–R
B) R–CO–R
C) R–CO–OH
D) R–OH
Page 44 of 209
47) Consider the following statements about alcohols:
(i) Alcohols contain a polar O–H bond and hence mix well with polar solvents like
water.
(iii) Alcohols have a higher boiling point compared to hydrocarbons with the same
number of carbon atoms.
A) none
C) (iii) only
E) all
A) acetone
B) glycerol
C) ethanol
D) cholesterol
Page 45 of 209
49) Which one of the following compounds is an isomer of CH3CH2CH2CH2OH?
A) CH3CH2CH2OH
A) R–O–R
B) R–CO–R'
C) R–CO–OH
D) R–OH
Page 46 of 209
51) Which of the following compounds do not contain an sp3 hybridized oxygen
atom?
A) ketones
B) alcohols
C) ethers
D) esters
52) How many chiral carbon atoms does the neopentane (2,2 - dimethylpropane)
have?
A) 0
B) 1
C) 2
D) 3
53) Proteins are biopolymers formed via multiple condensation coupling of which
two functional groups?
Page 47 of 209
52) Of the compounds below, __________ is an isomer of
Page 48 of 209
54) Which one of the following molecules is chiral?
55) Which of the following compounds does not contain a C=O bond?
A) ketones
B) aldehydes
C) esters
D) amides
E) ethers
Page 49 of 209
Answers
1.D 2.A 3.C 4.C 5.C 6.B 7.D 8.A 9.A 10.C
11.D 12.C 13.A 14.D 15.B 16.C 17.D 18.D 19.C 20.C
21.B 22.B 23.B 24.B 25.D 26.A 27.B 28.D 29.C 30.D
31.B 32.D 33.C 34.C 35.B 36.D 37.C 38.D 39.E 40.D
41.C 42.C 43.E 44.E 45.A 46.D 47.E 48.A 49.D 50.B
51.A 52.A 53.B 54.D 55.E
Page 50 of 209
Part 3 (EKB and some websites)
1-Using the IUPAC nomenclature, what name does the following alcohol have?
A) Hexan-3-ol
B) Hexan-5-ol
C) Hexan-2-ol
D) Hexan-4-ol
E) Hexan-1-ol
A) Fuel
B) Thermometers
C) Industrial solvent
D) Packaging
E) Antiseptic
Page 51 of 209
3- The incomplete reaction scheme below shows the synthesis of propanol from
chloropropane:
Which of the following reactants and conditions will result in the above
reaction?
C) They could be prepared from the reaction of alkyl halides with strong alkalis.
Page 52 of 209
5- Alcohols are prepared in the laboratory by the hydrolysis of alkyl halides in a
strong alkali, like potassium hydroxide (KOH). Which of the following alkyl
halides is the best choice for this reaction?
A) Alkyl bromide
B) Alkyl iodide
C) Alkyl chloride
D) Alkyl fluoride
A) – COOH
B) – SO3H
C) – CHO
D) – OH
E) – NH2
7- The given reactions show two different methods for the preparation of ethanol:
Page 53 of 209
A) Elimination
B) Halogenation
C) Fermentation
D) Hydrogenation
E) Polymerization
A) Catalytic hydration
B) Hydrogenation
C) Substitution
D) Decomposition
E) Elimination
A) CO2 and H2
B) CHCOOH and H2
C) CH2O and H2
Page 54 of 209
9- Glycerol can be used in all of the following except _____.
10- Sorbitol is a sugar alcohol that is found naturally in fruits, such as apples and
cherries, and that is commonly used as a substitute for sugar. Which of the
following describes sorbitol?
A) It is a polyhydric alcohol.
B) It is a trihydric alcohol.
C) It is a monohydric alcohol.
D) It is a dihydric alcohol.
12- Which of the following statements about the boiling point of ethylene glycol is
true?
Page 55 of 209
B) It is higher than those of ethanol and glycerol.
13- Ethanol reacts with sodium, producing sodium ethoxide and hydrogen gas.
Page 56 of 209
16- In addition to hydroxyl groups, which of the following functional groups can
be found in a molecule
of glucose?
A) – CHO
B) – CONH2
C) – COOH
D) – NH2
CI, I, Br
A) Br, I, Cl
B) Cl, Br, I
C) I, Br, Cl
D) I, Cl, Br
18- Which of the following is the common industrial method for the preparation of
ethanol in Egypt?
Page 57 of 209
19- Which of the following is the formula of 2-methylpropan-2-ol?
20- Which of the following is the correct formula for isobutyl alcohol?
Page 58 of 209
22- Which of the following is considered when classifying alcohols into primary,
secondary, or tertiary alcohols?
23- Since pure ethanol is expensive, a cheaper alternative that can be used as fuel
is converted alcohol, otherwise known as red spirit. It is a mixture of ethanol and
methanol along with other additives. Which of the following is a health risk
associated with methanol?
A) Stomach cancer
B) Skin irritation
C) Blindness
Page 59 of 209
25- Which of the following explains why ethanol is used in special thermometers
measuring temperatures as low as – 50° C?
26- Consider the following reaction:What product is formed from this reaction?
Page 60 of 209
27- Two different experiments were performed under different reaction conditions
with propan-1-ol.
A) A: propanone, B: propanal
B) A: propanal, B: propanone
28- Which of the following is true upon the reaction of ethanol with sodium metal?
Page 61 of 209
29- A piece of sodium metal was dropped into a sample of methanol.
A) Sodium methyl
B) Methanoic acid
C) Sodium methanoate
D) Methanal
E) Sodium methoxide
A) Water vapor
B) Hydrogen
C) Carbon dioxide
D) Oxygen
E) Methane
30- The reaction scheme below shows various reactions a molecule of propan-2-
olcan undergo:
Page 62 of 209
Which product would be a ketone?
A) A
B) B
C) C
A) 2-Chloropropan-2-ol
B) 2-Chloropropane
C) 1-Chloropropane
How many different positional isomers would result from the reaction to form
product A?
A) 1 isomer
B) 2 isomers
C) 4 isomers
D) 3 isomers
Page 63 of 209
E) The addition of an oxygen
A) Esters
B) Aldehyde
C) Carboxylic acid
D) Ketone
E) Amides
32- Fill in the blanks: Complete oxidation of ethanol using acidified potassium
dichromate solution produces _____ that has a ____ odor.
A) acetaldehyde, fruity
C) acetone, fruity
A) CuSO4
B) HgSO4
C) H2SO4
D) KMnO4
Page 64 of 209
E) K2CrO4
A) Ethyl ethanoate
B) Ethyl methanoate
C) Methyl formate
D) Methyl propanoate
E) Methyl ethanoate
A) Tertiary
B) Primary
C) Secondary
Page 65 of 209
Which of the following alcohols could the reactant be?
35- Excess ethanol was reacted with concentrated sulfuric acid at 130° C to
produce a product with the molecular formula C4H10O.The product was found not
to be an alkene or an alcohol. What class of molecule might the product be?
A) Ether
B) Ketone
C) Ester
D) Alkane
E) Anhydride
A) Carboxylic acids
B) Esters
C) Ketones
D) Aldehydes
Page 66 of 209
37- What type of reaction takes place between an alcohol and a carboxylic acid in
the presence of concentrated sulfuric acid?
A) Esterification reaction
B) Hydrogenation reaction
C) Addition reaction
38- If ethanol is heated at 140°C with concentrated sulfuric acid, how many
molecules of ethanol are needed to remove one molecule of water?
39- Which of the following is used as a catalyst in the reaction between ethanol
and hydrochloric acid?
A) V2O5
B) H2SO4
C) ZnCl2
D) K2Cr2O7
Page 67 of 209
40- Which of the following alcohols is not oxidized by chromic acid?
A) 2-Methyl-1-propanol
B) 2-Methyl-2-propanol
C) 2-Methyl-1-butanol
D) 3-Methyl-2-butanol
41- The product of the reaction between an alcohol and concentrated sulfuric acid
depends on the temperature. What is the class of the molecule produced if the
temperature is adjusted at 180°C?
A) Carboxylic acid
B) Alkene
C) Ketone
D) Ether
42- Which of the following can be used in detecting drivers’ intake of liquors?
A) Hydrogen chloride
B) Zinc chloride
C) Acetic acid
D) Potassium dichromate
Page 68 of 209
43.Which chemist is often credited with proposing and publishing the correct
structure of benzene?
A) Lavoisier
B) Kekulé
C) Faraday
D) Dalton
E) Hückel
44. Benzene is a planar, cyclic, hexagonal hydrocarbon that was first discovered by
the English scientist Michael Faraday in 1825. What is the molecular formula of
benzene?
A) C7H8
B) C6H6
C) C5H6
D) C6H12
E) C5H10
A) Electrical conductivity
E) An aromatic smell
Page 69 of 209
46.According to the IUPAC nomenclature, what name does the following benzene
derivative have?
A) Bromophenol
B) Benzene bromide
C) Bromophenyl
D) Benzyl bromide
E) Bromobenzene
meta position?
A) Br
B) CH3
C) COOH
D) NH2
E) OH
Page 70 of 209
48- Consider the following:
Using IUPAC convention, what name does the trisubstituted benzene have?
A) 1-Nitro-2-bromo-3-chlorobenzene
B) 2-Nitro-3-chloro-4-bromobenzene
C) 1-Bromo-2-chloro-3-nitrobenzene
D) 3-Bromo-2-chloro-1-nitrobenzene
E) 2-Bromo-3-chloro-4-nitrobenzene
49- The simplified reaction produces a disubstituted benzene. What is its name?
Page 71 of 209
A) a𝑛ti-Bromochlorobenzene
B) 𝑝ara-Bromochlorobenzene
C) ortho-Bromochlorobenzene
D) 𝑚eta-Bromochlorobenzene
E) 𝑠yn-Bromochlorobenzene
50- A reaction scheme for the synthesis of benzene is shown. What name is given
to this method?
A) Catalytic reforming
B) Reduction
C) Steam cracking
D) Polymerization
E) Dealkylation
51- Benzene can be prepared from its derivative, sodium benzoate, according to
the following reaction scheme:
Page 72 of 209
What other product is formed in this reaction?
A) Na2CO3
B) CH4
C) NaOCa
D) Ca(OH)2
E) CHOONa
A) Ethane
B) Ethene
C) Ethanol
D) Ethanoic acid
E) Ethyne
A) Benzene
B) Naphthalene
C) Anthracene
D) Diphenyl
Page 73 of 209
54- The radical formed by removing one hydrogen atom from a benzene
A) biphenyl
B) benzene
C) phenyl
D) benzyl
A) benzene
B) naphthalene
C) cyclohexane
D) gasoline
Page 74 of 209
57- What is the IUPAC name of the following aromatic compound?
A) 6-Fluoro-1,4-dichlorobenzene
B) 2-Fluoro-1,4-dichlorobenzene
C) 1,4-Dichloro-2-fluorobenzene
D) 1,4-Dichloro-6-fluorobenzne
58- What is the common name of the 4-chlorotoluene compound according to the
ortho-, para-, and meta- nomenclature?
A) meta-Chlorotoluene
B) meta-Chloromethyl benzene
C) ortho-Chlorotoluene
D) para-Chlorotoluene
59- The aromatic benzene could be synthesized in the laboratory through _____.
Page 75 of 209
60- The number of moles of hydrogen required to convert 1 mole of
A) 5
B) 6
C) 4
D) 3
62- A student, who has recently started studying organic chemistry, attempted to
write the nomenclature of a given organic compound and typed its IUPAC name as
3-bromo-2, 5-dichloro-1-methylbenzene. What is the mistake in this IUPAC
name?
Page 76 of 209
63- Which of the following is incorrect about benzene?
D) The bond length between the carbon atoms in benzene is intermediate between
the lengths of single and double bonds.
64.1- The following reaction shows the chlorination of benzene in the sunlight
(UV), producing gammexane:
A) Substitution reaction
B) Combustion reaction
C) Decomposition reaction
D) Addition reaction
A) Insecticide
B) Flavoring agent
C) Sweetening agent
D) Food preservative
Page 77 of 209
E) Detergent
65- The tosyl group is used extensively in organic synthesis, and it is the anionic
derivative of the tosylic acid shown. Which two reagents would react when
heated to form tosylic acid and water?
66- The reaction scheme shows how benzene can react with halogens in
Page 78 of 209
The reaction scheme shows how benzene can react with halogens in
Page 79 of 209
67- Consider the following reaction:
Page 80 of 209
68- Which of the following reactions is not a substitution reaction of benzene?
Page 81 of 209
69- Picric acid, also known as 2,4,6−trinitrophenol, is a benzene derivative
containing several nitro groups. Given the chemical groups it contains, what
primary use might picric acid have?
B) Fertilizers
C) Explosives
D) Food preservation
E) Paints
Page 82 of 209
71- What product will be formed from the alkylation of benzene as
Page 83 of 209
72- What product is produced from the hydrogenation of benzene using
A) Cyclohexene
B) Carbon dioxide
C) Ethyne
D) Cyclohexane
E) Hexane
Page 84 of 209
73- Consider the following reaction:
A) Ethylcyclohexane
B) Cyclohexene
C) Ethylbenzene
D) Ethylcyclohexene
E) Cyclohexane
A) Alkylation
B) Decomposition
C) Combustion
D) Addition
E) Substitution
Page 85 of 209
74- Which of the following choices shows the product (or products) of the reaction
of benzene with nitric acid in the presence of concentrated sulfuric acid?
A) Nitrobenzene only
A) addition or substitution
B) substitution only
C) addition only
D) substitution or elimination
76- What will happen to the red colour of bromine upon the addition of
Page 86 of 209
77- What functional group does a carboxylic acid contain?
A) – COR
B) – COOH
C) – CONH2
D) – COOR
E) – CHO
A) Benzoic acid
B) Phthalic acid
C) Butyric acid
D) Acetic acid
E) Formic acid
79- Fill in the blanks: Catalytic hydration of ______ produces _______ that is then
oxidized to form acetic acid.
A) ethene, acetaldehyde
B) ethane, acetaldehyde
C) acetylene, ethanol
D) acetylene, acetaldehyde
E) ethane, ethanol
Page 87 of 209
80- Benzoic acid can be prepared from the oxidation of toluene according to the
following reaction:
A) Al(C2H5)3
B) LiAlH4
C) V2O5
D) ZnCl2
E) CrO2Cl2
1. Benzoic acid
2. Acetic acid
3. Hydrochloric acid
4. Ethanol
Which of the following is the correct order of these compounds starting with
the least acidic one?
A) 3,1,2,4
B) 4,2,1,3
C) 3,2,1,4
D) 1,3,2,4
E) 3,2,4,1
Page 88 of 209
82- A selection of carboxylic acids encountered in everyday life is shown.
What is the name of molecule C that is often found in fruits such as oranges
and lemons?
A) Limonene
B) Oxalic acid
C) Dodecanoic acid
D) Citric acid
E) Maleic acid
A) E
B) F
C) D
D) B
Page 89 of 209
E) C
A) A
B) B
C) F
D) E
E) D
A) (A)
B) (B)
C) (C)
Page 90 of 209
D) (D)
E) (F)
84- The structure provided shows glycine, a molecule containing a carboxylic and
an amine group. What general name is given to the class of organic compounds
that glycine belongs to?
A) Anhydrides
B) Aromatics
C) Amino acids
D) Acid chlorides
E) Aldehydes
Which large biomolecules are formed from long chains of these molecules?
A) Lignin
B) Nucleic acids
C) Lipids
D) Proteins
E) Carbohydrates
Page 91 of 209
85- According to IUPAC nomenclature, which acid is commonly known as acetic
acid?
A) Propanoic acid
B) Butanoic acid
C) Ethanoic acid
D) Methanoic acid
E) Pentanoic acid
86- Which of the following correctly compares benzoic acid and phenol?
B) Benzoic acid can react with sodium hydroxide, while phenol cannot.
C) Phenol is more highly acidic than benzoic acid because the phenoxide ion is
more stable than the benzoate ion.
D) Benzoic acid is more highly acidic than phenol because the benzoate ion is
more stable than the phenoxide ion.
B) It is insoluble in water.
Page 92 of 209
88- Which of the following carboxylic acids can be formed in the human body?
A) Formic acid
B) Acetic acid
C) Lactic acid
D) Citric acid
89- Which of the following carboxylic acids has the molecular formula C8H6O4?
A) Citric acid
B) Benzoic acid
C) Salicylic acid
D) Phthalic acid
90- Which of the following carboxylic acids has two functional groups?
A) Oxalic acid
B) Phthalic acid
C) Salicylic acid
D) Benzoic acid
Page 93 of 209
91- Which of the following carboxylic acids could be used for the treatment of
acne?
A) Formic acid
B) Salicylic acid
C) Benzoic acid
D) Acetic acid
E) Lactic acid
92- Which of the following correctly compares carboxylic acids with alcohols?
A) Alcohols are more acidic than carboxylic acids because alcohols can form
dimers between their molecules.
B) Carboxylic acids are more acidic than alcohols because carboxylate anions are
stabilized by resonance, while alkoxides are not.
C) Carboxylic acids are more acidic than alcohols because carboxylic acids can
form dimers between their molecules.
D) Alcohols are more acidic than carboxylic acids because alkoxides are stabilized
by resonance, while carboxylate anions are not.
93- Which of the following carboxylic acids has the highest solubility in water?
A) Heptanoic acid
B) Octanoic acid
C) Hexanoic acid
D) Nonanoic acid
E) Ethanoic acid
Page 94 of 209
94-What is the molecular formula of butanoic acid?
A) C3HC5OOH
B) C3HC6OOH
C) C4HC9OOH
D) C3HC7OOH
E) C3HC8OOH
95- Which of the following is the correct order of boiling points of carboxylic
acids from highest to lowest?
A) CnH2n+1COOH
B) CnH2n+2COOH
C) CnH2nCOOH
D) CnHn+2COOH
E) CnH2n-1COOH
Page 95 of 209
97- Which of the following is not correct about carboxylic acids?
C) They have a lower boiling point than alcohols that have the same number of
carbon atoms.
D) They are more acidic than alcohols that have the same number of carbon atoms.
98- Which of the following carboxylic acids has the highest boiling point?
A) Butanoic acid
B) Ethanoic acid
C) Propanoic acid
D) Methanoic acid
E) Hexanoic acid
A) Terephthalic acid
B) Citric acid
C) Oxalic acid
D) Formic acid
E) Phthalic acid
Page 96 of 209
100- Which of the following reasons might cause the solubility of the carboxylic
acids in water to decrease?
101- Which of the following reagents could be used to detect carboxylic acids?
A) Bromine water
B) Sodium bromate
C) Potassium permanganate
D) Sodium carbonate
A) Aliphatic carboxylic acids are more acidic than alcohols that have the same
number of carbon atoms.
B) Aliphatic carboxylic acids have higher boiling points than alcohols that have the
same number of carbon atoms.
C) Aliphatic carboxylic acids are generally more acidic than aromatic carboxylic
acids.
Page 97 of 209
103- In an experiment, two test tubes were filled with ethanoic acid. A piece of
magnesium ribbon was dropped into one test tube, and some solid sodium
hydrogen carbonate (NaHCO3) was dropped into the other.
A) CH3COOHMg
B) CH3COOMg
C) HCOOMg
D) (CH3COO)2Mg
E) (HCOO)2Mg
The reaction with (NaHCO3) produces sodium acetate and two other
products. What are they?
A) O2 and CO
B) H2 and CO2
C) H2O2 and CO
E) HCOOH and O2
Page 98 of 209
104-Which of the following reactions is not an indication of the acidity of a
carboxylic acid?
A) Butan-1-ol
B) Ethanol
C) Butan-2-ol
D) Propan-1-ol
E) Propan-2-ol
What other reactant is needed in the process? How many moles are needed?
A) CH4
B) 2OH–
C) H2
D) 2H2
E) 2O2
Page 99 of 209
106- Consider the following reaction:
In a reaction with ethanol, which of the following carboxylic acids would produce
the ester?
A) Ethanoic acid
B) Propanoic acid
C) Methanoic acid
D) Butanoic acid
108- The reduction of a carboxylic acid with hydrogen and a CuCr2O4 catalyst
gives the following product:
110- Which of the following esters will be obtained when methanoic acid reacts
with ethanol?
A) HCOOCH3
B) HCOOC2H5
C) CH3CH2COOC2H5
D) CH3COOCH3
E) CH3COOC2H5
A) Concentrated H2SO4
B) Anhydrous CuSO4
C) Alkaline KMnO4
E) Alkaline K2CrO4
What is the name of the reaction that best describes the equation above?
A) Neutralization
B) Catalytic hydration
C) Addition
D) Esterification
E) Alkylation
A) The methyl group in acetic acid is replaced by the ethyl group in ethanol.
B) The methyl group in acetic acid is replaced by the ethoxide group in ethanol.
C) The hydroxyl group in acetic acid is replaced by the ethoxide group in ethanol.
D) The hydrogen atom in acetic acid is replaced by the ethyl group in ethanol.
116- Which of the following will be produced when propionic acid reacts with
calcium hydroxide?
A) (CH3COO)2Ca
B) CH3COOCa
C) C2H5COOCa
D) (C2H5COO)2Ca
a. 3 c. 5
b. 4 d. 6
a. 2 c. 4
b. 3 d. 5
4. When a carbon atom forms four covalent bonds, the bonds are directed toward
the corners of a
a. triangle. c. square.
b. pyramid. d. tetrahedron.
a. hydrogen c. oxygen
b. water d. carbon
a. –COOH c. –CO
b. –OH d. –O–
14. The name of a compound with the functional group –OH has the suffix
b. –al. d. one.
15. What are alkanes called when atoms of fluorine, chlorine, bromine, or iodine
are substituted for hydrogen atoms?
a. –OX c. –X
b. –XO d. –O–
17. In the figure above, to what class does the organic compound belong?
a. alcohols c. ethers
a. 1,2,3-propanetriol c. ethanol
b. 1,2-ethanediol d. 2-butanol
a. 2-bromopropyne c. 2-bromopropane
b. 2-bromopropene d. 2,2-bromopropene
a. 1,3-butadiene c. 2,3-butadiene
b. 1,4-butadiene d. 1,3-butene
a. ethane c. ethyne
b. ethene d. etha-di-ene
a. monomers c. polymers
d. have the same Lewis structure, but different molecular orbital energies.
d. enantiomers have different physical properties, such as melting point and color.
a. CH4
b. C2H2
c. C2H4
d. C2H6
e. C3H8
a. 1
b. 2
c. 3
d. 4
e. 8
a. C4H8
b. C10H20
c. C8H18
d. C5H12
e. C3H4
a. 4,5-dihexane
b. 2,3-diethylhexane
c. 4,5-dimethane
d. 2,3-dimethylhexane
e. 4,5-dimethylhexane
a. pentane
b. cyclopentane
c. pentanone
e. cyclopentene
a. 3-methyl-5-ethylheptane
b. 3,5-diethylhexane
c. 2-methyl-4-ethylpentane
d. 2,4-diethylhexane
e. 5-ethyl-3-methylheptane
32. Which of the following hydrocarbons can have cis and trans isomers?
a. butane
b. 2-pentyne
c. 3-hexene
d. 2-ethylbutane
e. propene
a. cis-4-propyl-3-butene
b. ethyl-propylethene
c. cis-ethyl-propylethene
d. cis-3-heptene
e. cis-5-ethyl-4-pentene
a. trans-acetylene
b. trans-1,3-pentadiene
c. trans-2,4-pentadiene
d. trans-4-methyl-1,3-butadiene
e. trans-4-methyl-1,3-butene
a. 4-methyl-2-pentyne
b. 4,4-dimethylbutyne
c. 4,4-dimethyl-2-butyne
d. 2-methyl-3-pentyne
e. 2-methyle-3,4-pentadyne
a. C6H6
b. C5H10
c. C5H9
d. C5H8
e. C5H6
a. C8H18
b. C9H20
c. C10H20
d. C10H22
e. C11H22
a. 3 only
b. 1 and 4
c. 2 only
d. 1, 2, and 4
a. 1 only
b. 2 and 3
c. 1, 2 and 3
d. 1, 3, and 4
e. 1 and 4
a. chloropropene
b. 1,3 dichloropropane
c. dichloropropane
d. 1,2-dichloropropyne
e. 1,3-dichloropropene
a. chloroethane
b. chloroethene
c. 1,2-dichloroethane
d. 1,1-dichloroethane
e. ethane
a. 2-hydroxybutane
b. 2,3-dihydroxybutane
c. cis-2-butene
d. butane
e. trans-2-butane
a. 1
b. 2
c. 4
d. 6
e. 8
a. p-dichlorobenzene
b. 3-dichlorobenzene
c. m-dichlorobenzene
d. dichlorobenzene
e. o-dichlorobenzene
a. 3-chlorobenzoic acid
b. 2-chlolobenzoic acid
d. 1-carbonate-3-chlorobenzene
e. 3-chlorotoluene
48. All of the statements below concerning hydrocarbons are correct EXCEPT
a. C2H6
b. CH3CO2H
c. CH3CHO
d. CH3CH2OH
e. CH3OCH3
a. alcohol
b. amine
c. amide
d. ester
e. ether
a. ether
b. ester
c. amide
d. aldehyde
e. amine
a. ester
b. alcohol
c. amine
d. aldehyde
Page 122 of 209
e. amide
54. The C=O linkage occurs in molecules with the following functional groups
EXCEPT ________.
a. esters
b. ketones
c. amines
d. carboxylic acids
e. aldehydes
55. All of the following functional groups are members of the class of compounds
known as carbonyls EXCEPT
a. amides.
b. ethers.
c. aldehydes.
d. carboxylic acids.
e. ketones.
a. ketone
b. aldehyde
c. ester
d. amine
e. amide
a. HCl
b. NaBH4
c. NaH
d. K
e. KMnO4
a. 3-hexanol
b. 2-butanol
c. ethylene glycol
d. 2,3-butanediol
e. methanol
59. Compounds from which class usually have offensive odors, such as that of
decaying meat or bad breath?
a. esters
b. ketones
c. amines
d. alcohols
e. carboxylic acids
a. ketone
b. alcohol
c. ester
d. alkane
e. carboxylic acid
1. ANS: B
2. ANS: B
3. ANS: C
4. ANS: D
5. ANS: C
6. ANS: B
7. ANS: D
8. ANS: D
9. ANS: C
10. ANS: D
11. ANS: C
12. ANS: B
13. ANS: B
14. ANS: A
15. ANS: C
16. ANS: C
17. ANS: A
18. ANS: A
19. ANS: B
20. ANS: A
21. ANS: B
22. ANS: C
23. ANS: B
24. ANS: C
Page 126 of 209
25. ANS: D
26. ANS: C
27. ANS: C
28. ANS: E
29. ANS: D
30. ANS: B
31. ANS: E
32. ANS: C
33. ANS: D
34. ANS: B
35. ANS: A
36. ANS: D
37. ANS: C
38. ANS: A
39. ANS: E
40. ANS: A
41. ANS: E
42. ANS: B
43. ANS: A
44. ANS: D
45. ANS: D
46. ANS: C
47. ANS: A
48. ANS: C
49. ANS: D
50. ANS: A
51. ANS: D
Page 127 of 209
52. ANS: B
53. ANS: B
54. ANS: E
55. ANS: C
56. ANS: B
57. ANS: A
58. ANS: E
59. ANS: A
60. ANS: C
61. ANS: E
(d) Bonds which bind the atoms together are nearly always ionic.
Answer. (d)
(a) oxygen
(b) sulfur
(c) nitrogen
(d) silicon
Answer. (d)
(b) Fermentation
(d) Atmosphere
Answer. (a)
Answer. (a)
(a) 2 bonds
(b) 4 bonds
(c) 3 bonds
(d) 5 bonds
Answer. (b)
Answer. (a)
Answer. (c)
Answer. (a)
Answer. (a)
Answer. (b)
11. Compound in which carbons use only sp3 hybrid orbitals for bond
formation is
(a) CH3CH2CH3
(b) CH3C≡CH
(c) CH3CH=CH2
(d) CH2=CH—CH=CH2
Answer. (a)
12. Compound in which carbon uses sp3 hybrid orbitals for bond formation
Is
Answer. (c)
14. Compound in which carbons use only sp2 hybrid orbitals for bond
formation is
Answer. (c)
(a) Formaldehyde
(b) Acetone
Answer. (a)
(a) 180°
(b) 120°
(c) 109.5°
(d) 115.5°
Answer. (c)
(a) 60°
(b) 109.5°
(c) 120°
(d) 118°28′
Answer. (b)
(a) 60°
(b) 120°
(c) 90°
(d) 180°
Answer. (b)
(a) 1.20 Å
(b) 1.34 Å
(c) 1.54 Å
(d) 1.68 Å
Answer. (b)
Answer. (a)
Answer. (a)
22. Which of the following hydrocarbons has the shortest C–C bond length?
(a) CH2=CH2
(b) CH3CH3
(c) HC≡CH
(d)
Answer. (c)
(a) CH2=CH2
(b) CH3CH3
(c) HC≡CH
(d)
Answer. (b)
(c) sp, sp
(d) sp2, sp
Answer. (d)
(a) 0
(b) 1
(c) 2
(d) 3
Answer. (c)
(b) Resonance hybrids are more stable than any individual resonance form.
(c) Resonance hybrids are averages of all resonance forms resembling the less
stable forms.
Answer. (d)
(b) formaldehyde
(d) 1,3-butadiene
(a) cis-1,2-dichloroethylene
(b) o-dichlorobenzene
(c) trans-1,2-dichloroethylene
(d) p-dichlorobenzene
(a) Cl2
(b) CO2
(c) CCl4
(d) CHCl3
Answer. (d)
(b) chloromethane
(c) dichloromethane
(d) chloroform
Answer. (a)
(a) CH3Cl
(b) CH3Br
(c) CH3F
(d) CH3I
Answer. (c)
(a) dichloromethane
(b) chloroform
(c) chloromethane
Answer. (a)
(c) Carbanions
Answer. (a)
35. Homolytic fission of covalent bond between carbon atoms will produce:
Answer. (c)
Answer. (a)
Answer. (a)
Answer. (d)
Answer. (b)
(a) methyl
(b) primary
(c) secondary
(d) tertiary
Answer. (d)
Answer. (b)
(a) NH3
(b) Br+
(c) AlCl3
(d) NO2+
Answer. (a)
Answer. (b)
(a) AlCl3
(b) H3O+
(c) BF3
(d) CN–
Answer. (d)
(a) NH3
(b) HSO3–
(c) AlCl3
(d) HO–
Answer. (c)
(d) NH3
Answer. (b)
(a) AlCl3
(b) CH3OH
(c) NH3
(d) CH3OCH3
Answer. (a)
Answer. (a)
Answer. (d)
Answer. (c)
(c) The greater the number of relatively stable resonance contributors, the
Answer. (b)
(a) Curved arrows are always drawn from an electron poor center to an
(b) A doubled headed arrow means one electron has been moved.
(c) Curved arrows are always drawn from an electron rich center to an electron
poor center.
Answer. (c)
Answer. (b)
Answer. (a)
55. What is the name given for a species that contains a positively charged
carbon atom?
(a) carbanion
(b) carbocation
Answer. (c)
(a) sp3–sp3
(b) sp2–sp3
(c) s–p
(d) s–sp2
Answer. (d)
(a) s
(b) sp
(c) sp2
(d) sp3
Answer. (d)
58. An increase in which of the following results in a decrease in the rate of the
chemical reaction?
(a) temperature
(b) concentration
Answer. (d)
59. The reaction step that has its transition state at the highest point on the
Answer. (a)
Answer. (c)
Answer. (d)
(a) NH3
(b) CH3NH2
(c) HC≡C:–
(d) CH3CH2+
Answer. (d)
(a) FeBr3
(b) Br–
(c) NH3
(d) CH3OCH3
Answer. (a)
Answer. (a)
Answer. (b)
(a) HCl
(b) CH3Cl
(c) H2
(d) NH3
Answer. (c)
67.Two compounds have the same composition and also have the same atoms
attached to the same atoms, although with different orientations in space. These
compounds are
(a) Identical
(d) Stereoisomers
Answer. (d)
Answer. (b)
(a) Alkoxides
(c) Isomers
Answer. (c)
70. Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3) are best considered :
(b) stereoisomers
(c) enantiomers
(d) diastereomers
Answer. (a)
(a) Enantiomers
(c) Metamers
Answer. (c)
Answer. (d)
1.
2.
3.
4.
5.
7.
8.
9.
10.
12.
13.
14.
16.
17.
18.
Page 157 of 209
19.
20.
21.
22.
23.
Page 158 of 209
24.
25.
54) One mole of hydrocarbon X reacts with one bromine mole and the
product is saturated hydrocarbon contains one bromine atom so X is ----
-and the reaction is------
A) alkene- addition C) alkane - substitution
B) alkyne - substitution D) alkyne - Addition
56) One mole of hydrocarbon X reacts with TWO bromine mole and the
product is saturated hydrocarbon contains FOUR bromine atoms so X is
-----and the reaction is------
A) Alkane substitution C) alkene -substitution
B) Alkene -Addition D) Alkyne -Addition
57)
59)
60)
62)
63)
65)
Q1- c
Q2- c
Q3-c
Q4-d
Q5-a
Q6-d
Q7-c
Q8-d
Q9-b
Q10-b
Q11-d
Q12-c
Q13-d
Q14-c