Chapter 1.

1. What is the best description of the covalent bonds?
A) Results from the transfer of electrons from one atom to another.
B) Results from the sharing of electrons between two nuclei
C) Results from the attractive force between a hydrogen atom covalently
bonded to a very electronegative atom
D) Results from the sharing of an electron pair from a single atom
2. Which information can you have from Lewis structure?
A) Numbers of lone pairs electrons present in each or the atoms
B) Chemical bonding between atoms in a molecule
C) The placement of electrons between atoms
D) All of these statements

3. What is the best description of resonance structures? 4. Give carbon hybridization having an orbital with 33% s-character.
A) Structures having the same placement of atoms but different arrangement of A) sp
electrons
B) sp2
B) Structures having the same molecular formular but different bonding atomic
organization and bonding patterns C) sp3
C) Structures having the same molecular formular but different spatial D) none of these statements
arrangements of atoms
D) Structures having the same placement of atoms but different by rotation along
single bonds

5. Rank the bond length and bond strength among three types of following carbon 6. Give the number of lone pairs in Lewis structure of urea, CO(NH 2)2
hybridization: sp, sp2, and sp3. A) 2
A) Increasing both bond length and bond strength B) 3
B) Decreasing both bond lenghth and bond strength C) 4
C) Increasing bond length and decreasing bond strength D) 5
D) Decreasing bond length and increasing bond strength
 Chapter 1.
7. Give the number of resonance structures for this resonance hybrid 8. Give molecular shape of amonia (NH3)
+ A) Trigonal planar
B) Trigonal pyramid
A) 4 + + C) Linear
B) 5 D) Tetrahedral
C) 6
D) 7 +

9. Rank three molecules H2C=O, BF3, and NH3 by increasing their polarity 10. What types of orbital do the lone pairs on oxygene reside in a
H2C=O molecule
A) BF3 < H2C=O < NH3
A) p-orbital and sp2 orbital
B) H2C=O < NH3 < BF3
B) each in a p-orbital
C) BF3 < NH3 < H2C=O
C) each in a sp2 orbital
D) NH3 < H2C=O < BF3
D) each in a sp3 orbital
 1. What is the best description of the Lewis acid?
Chapter 2.
A) A chemical species contains an empty orbital which is capable of
accepting an electron pair; an electron pair acceptor
B) A chemical species that can donate a pair of nonbonding electrons;
electron pair donor
C) A chemical species that is capable of donating a proton; a proton donor
D) A chemical species that is capable of accepting a proton; a proton
acceptor
3. Give a correct favorable formation of acid-base reaction
A) Reaction favors formation of the stronger acid and base
B) Reaction favors formation of the stronger acid and weaker base
C) Reaction favors formation of the weaker acid and stronger base
D) Reaction favors formation of the weaker acid and base
5. How do the intermolecular forces relate to boiling point and melting point
of an organic substance.
A) Increasing strength of intermolecular forces, decreasing boiling point and
melting point
B) Increasing strength of intermolecular forces, decreasing boiling point and
increasing melting point
C) Increasing strength of intermolecular forces, increasing boiling point and
decreasing melting point
D) Increasing strength of intermolecular forces, increasing boiling point and
melting point
2. How does pKa relate to Ka and acid strength?
A) The smaller pKa, the smaller Ka and the stronger acid
B) The smaller pKa, the smaller Ka and the weaker acid
C) The smaller pKa, the larger Ka and the stronger acid
D) The smaller pKa, the larger Ka and the weaker acid
4. Give a correct statement
A) The acidity of H-A increases with the presence of electron-withdrawing
groups in A
B) The acidity of H-A increases with the presence of electron-donating groups
in A
C) The acidity of H-A does not affect by presence of a constituent group in A
D) The more acidity, the less stable conjugate base
6. What is the best description on hydrophobic and/or hydrophilic
moieties?
A) Hydrophobic moiety is a nonpolar part of a molecules that is not
attracted to water. Hydrophilic moiety is a polar part of a molecules
that is attracted to water.
B) Hydrophobic moiety is a polar part of a molecules that is attracted to
water. Hydrophilic moiety is a nonpolar part of a molecules that is not
attracted to water.
C) Hydrophobic moiety easily dissolve in polar solvents.
D) Hydrophilic moiety easily dissolve in nonpolar or weakly polar
solvents.
 Chapter 2.
7. Identify functional groups in each isomer having 8. Rank the compounds in order to increase boiling point
molecular formular C4H10O A) (CH3CH2CH2)2O, CH3(CH2)5OH, CH3CH2CH2COOH
A) Aldehyde or alcohol B) (CH3CH2CH2)2O, CH3CH2CH2COOH, CH3(CH2)5OH
B) Alcohol or ether C) CH3CH2CH2COOH, CH3(CH2)5OH, (CH3CH2CH2)2O
C) Ether or ketone D) CH3(CH2)5OH, (CH3CH2CH2)2O, CH3CH2CH2COOH
D) Ketone or aldehyde

9. Which of the following hydrogen atom is the most acidic hydrogen 10. Rank the compounds in order to increase acidity

A) I II OH OH OH

B) II HO
H
A) I, II, III
C) III I O
O
B) II, III, I H3C Cl
O2N
D) IV
HO C) III, I, II I II III
D) I, III, II
HO OH
III IV
 Chapter 3.
1. What is the best description for the parent chain in alkanes? 2. Which points are required for numbering carbon atom in the carbon
A) A Carbon chain contains highest numbers of substituted groups skeleton of alkanes and cycloalkanes
B) A longest carbon chain A) Start with the chain end more near to a substituent
C) A longest carbon chain contains double bond B) Gives the lower number to the substitutent that appears first in the name
D) A ring contains highest number of carbons C) Numbering directions follows the first point of difference method
D) All of these statements
3. Give a correct IUPAC name of bellow compound
A) 2-isopropyl-2,6,6-trimethylheptane 4. Give a correct IUPAC name of bellow compound
B) 2,3,3,7,7-pentamethyloctane A) 1-sec-butyl-3-methylcyclohexane
C) 2,2,6,6,7-pentamethyloctane B) 1-methyl-3-sec-butylcyclohexane
D) 2,6,7-pentamethyloctane C) (Cis)-1-sec-butyl-3-methylcyclohexane
D) (Trans)-1-methyl-3-sec-butylcyclohexane

5. Which is a correct description on physical properties of alkanes 6. Give number of different staggered and eclipsed
A) Alkanes are soluble in water conformations along C2-C3 of n-butane.
B)Melting point increases with increased symmetry A) 3
C) Boiling point increases with branching B) 4
D) Melting point and boiling point decrease as the number of carbons increases C) 5
D) 6
 Chapter 3.
8. Which statement is incorrect on reaction of alkyl halides
7. Rank following conformations in order to increase of stability
A) Alkyl halides undergo nucleophilic substitution reactions with nucleophiles
B) Alkyl halides undergo dehydrohalogenation reactions with Bronsted-Lowry
bases
C) Alkyl halides undergo electrophilic substitution reactions with benzene
III IV
I II derivatives
D) Alkyl halides undergo elimination reactions with Lewis acids
A) IV, II, I, III
B) IV, I, II, III
C) II, IV, I, III
10. Give number of possible isomers formed by
D) I, IV, III, II
dehydrohalogenation of 2-bromo-4-methylpentane
A) 1
9. Rank the compounds in order to increase melting point B) 2
A) CH3(CH2)6CH3, (CH3)3CC(CH3)3, CH3CH(CH3)CH2CH2CH2CH2CH3 C) 3
B) (CH3)3CC(CH3)3, CH3CH(CH3)CH2CH2CH2CH2CH3, CH3(CH2)6CH3 D) 4
C) CH3CH(CH3)CH2CH2CH2CH2CH3, (CH3)3CC(CH3)3, CH3(CH2)6CH3
D) CH3CH(CH3)CH2CH2CH2CH2CH3, CH3(CH2)6CH3, (CH3)3CC(CH3)3
 Chapter 4. 2. Identify degree of unsaturation in a compound with
1. Which information can you have from degree of unsaturation (index of molecular formula C9H6O3
hydrogen deficiency)
A) 5
B) 6
A) Number of π-bonds in a molecule
C) 7
B) Number of rings in a molecule
D) 8
C) Number of double bonds or triple bonds in a molecule
D) Number of π-bonds and rings in a molecule
4. Give correct geometric isomers of below compounds
3. Give a correct IUPAC name of bellow compound
Br
A) I-Cis and II-Z CH3(CH2)7 (CH2)7COOH
A) 6-ethyl-1-methylcyclohexene B) I-Trans and II-Z
B) 3-ethyl-2-methylcyclohexene C) I-Cis and II-E
C) 1-ethyl-2-methylcyclohex-2-ene D) I-Trans and II-E
Br
D) 1-methyl-6-ethylcyclohexene I II

6. Give numbers of constitutional isomers of alkyne having

5. Which is correct description on physical properties of alkenes
molecular formula C6H10
A) Alkenes are soluble in water and insoluble in organic solvents
B) Cis-isomer is more polar than Trans-isomer A) 5
C) Trans-isomer has lower melting point than Cis-isomer B) 6
D) Alkenes have higher melting point and boiling point than corresponding C) 7
alkanes D) 8
 Chapter 4.
7. Which statement is correct on chemical properties of alkenes and alkynes 8. Give major product of Markovnikov addition of water to alkynes except
A) The π-bond is stable and hard to broken in reactions acetylene
B) Alkenes and ankynes easily involve addition reactions A) A ketone
C) Simple alkenes and ankynes easily react with nucleophiles or bases B) An aldehyde
D) Addition reaction of ankenes typically give a pair of Cis-enantiomers C) An alcohol
D) An ether

10. Give major product(s) of bellow reactions

1. NaH
9. Give major product of reaction between terminal alkynes with 1
H3C C CH
equivalent of hydrogen halide 2. Bromocyclohexane
A) E or Z vinyl halide compound
B) An alkenyl halide that H atom bond to the terminal carbon
C) A saturated compound that both halogen atoms bond to the terminal A) CH3-C≡CNa + H2
carbon B) Propynylcyclohexane
D) A saturated compound that both H atoms bond to the terminal carbon C) Cyclohexene
D) Propylcyclohexane
 Chapter 5.
1. Which statement is correct about alcohols.
2. Which statement is incorrect about epoxides.
A) Alcohols are any organic compounds that contain carbon-oxygen σ bond
A) Epoxides are named in three different ways, including epoxyalkanes,
B) Alcohols are classified into primary, secondary, tertiary, and quaternary
oxiranes, and alkene oxides
order
B) Epoxides are ether having the oxygen atom in a three-membered ring
C) Alcohols are water soluble
C) Epoxides are capable of intermolecular hydrogen bonding
D) Alcohols are organic compounds that carry at least
D) Epoxides are soluble in organic solvents
one hydroxyl group bound to a saturated carbon atom.

4. Rank capable of intermolecular hydrogen bonding and steric hindrance

3. Give a compound that has anaesthetic property
among primary, secondary and tertiary alcohols
A) Ethanol
A) Increasing both ability to hydrogen bonding and steric hindrance
B) Diethyl ether
B) Increasing ability to hydrogen bonding and decreasing steric hindrance
C) Methanol
C) Decreasing ability to hydrogen bonding and increasing steric hindrance
D) Dimethyl ether
D) Decreasing both ability to hydrogen bonding and steric hindrance

5. Which compound is synthesized through an intramolecular S N2

6. Which statement is correct about general reactions of alcohols, ethers, and
reaction epoxides.
A) A alcohol A) Nucleophilic groups react with epoxides but do not react with neither alcohols
B) An ether nor ethers
C) An epoxide B) Ethers undergo dehydration to give alkenes
D) All of these statements C) Alcohols generally react with halide anions to give alkyl halides
D) Ethers react with strong acid to give corresponding alcohols
 Chapter 5.
7. Give a correct statement on dehydration of alcohols to form alkenes 8. Give mechanism of ether cleavage reaction
A) Reactivity decreases as decreasing of alcohol order A) Only SN1
B) Major product is followed Zaitsev rule B) Only SN2
C) Reaction occur through E1 or E2 mechanism C) Both SN1 and SN2
D) All of these statements D) All of these statements

10. The 2,2-dimethylcyclopentanol underwent dehydration in sulfuric acid

9. Give a correct statement on the ring opening reaction of epoxides to form alkenes. Give the best description for the product(s)
A) Reaction occurs with front-side attack
B) Reaction mechanism follows SN1 with nucleophilic attack
C) Reaction mechanism follows SN2 with electrophilic attack
D) Reaction gives a final product containing at least an alcohol functional group
A) I
B) II, III, and IV I II III IV
C) I, II, III, and IV
D) None among I-IV
 Chapter 6.
2. Which of following names are groups
1. Which statement is incorrect for structure of benzene
A) benzene and benzyl
A) Benzene has the shape of a regular hexagon
B) benzyl and phenyl
B) All C–C bonds have the same length
C) phenyl and phenol
C) Benzene has alternating single and double bonds
D) phenol and benzene
D) π-electrons are delocalized over the six carbon atoms of the ring

4. Which statement is incorrect in nomenclature of polysubstituted benzene

3. Prefixes ‘ortho’ and ‘meta’ are used to name benzene derivatives with derivatives
following numbers A) benzene or a special benzene derivative is a parent chain
A) 1,2-disubtitutions and 1,3-disubtitutions B) substituents appear in alphabetical order
B) 1,2-disubtitutions and 1,4-disubtitutions C) number the ring in the direction that gives the lowest number at the first
C) 1,3-disubtitutions and 1,4-disubtitutions point of difference
D) 1,2,4-trisubtitutions and 1,3,4-trisubtitutions D) substituents are placed with numbers of the following prefixes ortho, meta,
and para
5. Give a correct IUPAC name for bellow compound
CH3 6. Give the best description of a aromatic compound
A) 1-ethoxy-2-ethyl-5-methylbenzene
A) a cyclic compound
B) meta-ethoxy-para-ethyltoluene
B) planar and comletely congugated system
C) 2-ethoxy-4-methylethylbenzene
C) contains 4n + 2 numbers of π electrons
D) 3-ethoxy-4-ethyltoluene
OCH2CH3 D) all of these statements
CH2CH3
 Chapter 6.
7. Compare stability of following molecules
8. Give numbers of π electrons in this molecule
H
A) 8 N
B) 10
N
benzene (I) hexa-1,3,5-triene (II) cyclobutadiene (III) buta-1,3-diene (IV) C) 12
D) 14 N

A) (I) is more stable than (II), (III) is more stable than (IV)
B) (II) is more stable than (I), (III) is more stable than (IV)
C) (I) is more stable than (II), (IV) is more stable than (III)
D) (II) is more stable than (I), (IV) is more stable than (III)
10. Give the most acidic hydrogen atom among bellow molecules
9. Which molecule is an aromatic compound
H H H H
C C C C
CH2 CH CH CH
HC HC HC HC N
CH CH CH CH H
HC HC HC HC H H H
CH CH CH CH
C C C C penta-1,4-diene cyclopentadiene pyrrole cyclopropene
H H H H
cycloheptatriene cycloheptatrienyl cation cycloheptatrienyl anion cycloheptatrienyl radical
A) penta-1,4-diene
B) cyclopentadiene
C) pyrrole
A) Cycloheptatriene
D) cyclopropene
B) Cycloheptatrienyl radical
C) Cycloheptatrienyl anion
D) Cycloheptatrienyl cation
 Chapter 7.
1. Which statement is incorrect on structure of aldehydes, ketones, and
carbonyl group
A) The carbonyl group consists of one σ-bond and one π-bond
B) The functional group of an aldehyde is a carbonyl group bound to at least
one H-atom
C) The functional group of a ketone is a carbonyl group bound to two carbon
atoms
D) The carbonyl group is strong electron donating group
3. Which statement is incorrect on the tautomerism and tautomers
A) Tautomerism commonly results from the relocation of a hydrogen atom with
thin the compound
B) Contitutional isomers are tautomers
C) Tautomers readily interconvert each other
D) The two tautomers of an amino acid are neural and zwitterionic forms
5. Give a method to synthesize aldehydes
A) Oxidation of secondary alcohols with PCC (Pyridinium chlorochromate)
B) Hydration of alkyne, except acetylene
C) Hydroboration-oxidation of terminal alkyne
D) By Friedel-Crafts acylation
2. Which statement is incorrect on nomenclature of aldehydes and ketones
A) Change the suffix ‘ane’ of the corresponding alkane in ‘anal’ to indicate
the aldehyde functional group, and in ‘anone’ to indicate the ketone
functional group
B) The main chain is the longest continuous chain of carbon atoms
C) In cyclic molecules which the -CHO group is connected to the ring, the
name is given by adding the suffix ‘carbaldehyde’ to the name of the ring.
D) In ketones, numbering direction that gets the lowest number of carbonyl
group.
4. Which statement is incorrect on physic properties of aldehydes and ketones
A) Aldehydes and ketones exhibit dipole–dipole interactions
B) Aldehydes and ketones are soluble in organic solvents
C) Aldehydes and ketones have lower boiling point and melting point
compare to corresponding alcohols
D) Aldehydes and ketones are capable of intermolecular hydrogen bonding.
6. Give possible products of the oxidative cleavage of an alkene by ozonolysis
reaction
A) two aldehydes
B) two ketones
C) an aldehyde and a ketone
D) all of these products
 Chapter 7.
7. Which is incorrect general feature-reactions of aldehydes and ketones

A) Nucleophilic addition to the carbonyl group 8. What alkene yields acetone and formaldehyde after treatment with
B) Reaction of carbonyl group with a Bronsted or Lewis base ozone followed by CH3SCH3
C) Reaction of carbonyl group with a Bronsted or Lewis acid A) Ethene
D) Reaction at alpha-carbon of carbonyl group B) 2,3-dimethylbut-2-ene
C) 2-methylpropene
9. Which of the following reactions give a proposed product D) Cis or Trans-but-2-ene

I + H2N

CHO 10. Give numbers of constitutional isomers of C 8H12 which undergoes the
oxidative cleavage of alkenes to give only 3-oxobutanal
+
II
CHO
H2N
(CH3COCH2CHO).
N
A) 1
III + O
B) 2
NH2
C) 3
D) 4
IV + O
NH2

A) I
B) II
C) III
D) IV
 Tautomerism of Vitamin C

Acid form
HO HO
H H
HO O HO
O O
OH

The most acidic

HO OH O OH
hydrogen atom in
Vitamin C

Conjugate base HO
H
HO
H
HO O HO O
O O

O OH O OH