Question 1

Find the correct statement about cis-trans isomers.

Accepted Answer

A)  Cis-trans isomers are diastereomers and occur because the rotation around a C≡C bond is very restricted. 
B)  Cis-trans isomers are enantiomers and occur because the rotation around a C=C bond is very restricted. 
C)  Cis-trans isomers are diastereomers and occur because the rotation around a C=C bond is very restricted. 
D)  Cis-trans isomers are superimposable constitutional isomers of substituted alkenes formed around a C=C bond. 
E)  Cis-trans isomers are chiral molecules and occur because the rotation around a C=C bond is very restricted. 
A)  Cis-trans isomers are diastereomers and occur because the rotation around a C≡C bond is very restricted. 
B)  Cis-trans isomers are enantiomers and occur because the rotation around a C=C bond is very restricted. 
C)  Cis-trans isomers are diastereomers and occur because the rotation around a C=C bond is very restricted. 
D)  Cis-trans isomers are superimposable constitutional isomers of substituted alkenes formed around a C=C bond. 
E)  Cis-trans isomers are chiral molecules and occur because the rotation around a C=C bond is very restricted.

Question 2

Which of the following lists the substituents in the order of priority, from highest (priority 1) to lowest (priority 4)?

Accepted Answer

A)  -Cl, -CH2CH3, -CH=CH2, -CH3 
B)  -OH, -CH2CH3, -CH=CH2, CH3 
C)  -NH2, -CONH2, -COOH, CH3 
D)  -NH2, -COOH, -C(=O)H, -CH3 
E)  -Cl, -Br, -OH, -H 
A)  -Cl, -CH2CH3, -CH=CH2, -CH3 
B)  -OH, -CH2CH3, -CH=CH2, CH3 
C)  -NH2, -CONH2, -COOH, CH3 
D)  -NH2, -COOH, -C(=O)H, -CH3 
E)  -Cl, -Br, -OH, -H

Question 3

Match the following.
-

Accepted Answer

A) amine 
B) ketone 
C) aldehyde 
D) carboxylic acid 
E) ester
F)alcohol 
A) amine 
B) ketone 
C) aldehyde 
D) carboxylic acid 
E) ester
F)alcohol

Question 4

Which of the following compounds exhibit cis-trans isomerism?

Accepted Answer

A)  CH2=CH-CH3 
B)  CCl2=CBr2 
C)  CH3-CH=CH-CH3 
D)  CCl2=CHBr 
E)  (CH3)2C=CH(CH3) 
A)  CH2=CH-CH3 
B)  CCl2=CBr2 
C)  CH3-CH=CH-CH3 
D)  CCl2=CHBr 
E)  (CH3)2C=CH(CH3)

Question 5

Which of the following compounds is an alcohol?

Accepted Answer

A)  CH3CH2CH2C(=O)OH 
B)  CH3-O-CH2CH3 
C)  CH3CO2CH3 
D)  CH2OH-CH2OH 
E)  CH3CH2CH=O 
A)  CH3CH2CH2C(=O)OH 
B)  CH3-O-CH2CH3 
C)  CH3CO2CH3 
D)  CH2OH-CH2OH 
E)  CH3CH2CH=O

Question 6

Which of the following condensed general formulas represents tertiary alcohols?

Accepted Answer

A)  RCH2OR 
B)  RCH2OH 
C)  R3COR 
D)  R3COH 
E)  R3CCH2OH 
A)  RCH2OR 
B)  RCH2OH 
C)  R3COR 
D)  R3COH 
E)  R3CCH2OH

Question 7

Identify hybridization of carbon atoms numbered 1-6 in the structure below:

Accepted Answer

A)  Carbons 3, 4, and 6 are sp3, carbons 1, 2 and 5 are sp hybridized. 
B)  Carbons 2, 3, and 4 are sp3, carbons 1, 5, and 6 are sp2 hybridized. 
C)  Carbons 2, 3, 4, and 6 are sp3, carbons 1 and 5 are sp2 hybridized. 
D)  Carbons 2, 3, 4, and 6 are sp3, carbons 1 and 5 are sp hybridized. 
E)  Carbons 3, 4, and 6 are sp3, carbons 1, 2, and 5 are sp2 hybridized. 
A)  Carbons 3, 4, and 6 are sp3, carbons 1, 2 and 5 are sp hybridized. 
B)  Carbons 2, 3, and 4 are sp3, carbons 1, 5, and 6 are sp2 hybridized. 
C)  Carbons 2, 3, 4, and 6 are sp3, carbons 1 and 5 are sp2 hybridized. 
D)  Carbons 2, 3, 4, and 6 are sp3, carbons 1 and 5 are sp hybridized. 
E)  Carbons 3, 4, and 6 are sp3, carbons 1, 2, and 5 are sp2 hybridized.

Question 8

Determine the absolute configuration of the molecule shown below:

Accepted Answer

A)  R configuration 
B)  S configuration 
C)  E configuration 
D)  Z configuration 
E)  d configuration 
A)  R configuration 
B)  S configuration 
C)  E configuration 
D)  Z configuration 
E)  d configuration

Question 9

The infrared spectrum of a compound with molecular formula C6H8O has weak peaks around 1650 cm-1 and a strong peak around 1775 cm-1. What is the most likely structure of this compound?

Accepted Answer

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

Question 10

Which of the following pairs of organic compound families could have constitutional isomers?

Accepted Answer

A)  an ether and an alcohol 
B)  an amide and an amine 
C)  an ether and a carboxylic acid 
D)  a carboxylic acid and an amide 
E)  an amine and an alcohol 
A)  an ether and an alcohol 
B)  an amide and an amine 
C)  an ether and a carboxylic acid 
D)  a carboxylic acid and an amide 
E)  an amine and an alcohol

Question 11

Explain the concept of bond polarization and inductive effect using organic halides as an example.

Accepted Answer

Halogen atoms are more electronegative t

Question 12

Find the correct Newman projection formula showing a staggered conformer of n-hexane.

Accepted Answer

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

Question 13

What are the possible combinations of multiple bonds and rings if a compound's index of hydrogen deficiency equals 3?

Accepted Answer

A)  three rings; two rings and two double bonds; one ring and two triple bonds 
B)  three rings; two rings and a triple bond; one ring and two triple bonds; three triple bonds 
C)  three rings; two rings and a double bond; one ring and two double bonds; one ring and one triple bond; one double bond and one triple bond 
D)  three rings; two rings and a double bond; one ring and two double bonds; one ring and two triple bonds 
E)  two rings; two rings and a double bond; one ring and two double bonds; one ring and one triple bond 
A)  three rings; two rings and two double bonds; one ring and two triple bonds 
B)  three rings; two rings and a triple bond; one ring and two triple bonds; three triple bonds 
C)  three rings; two rings and a double bond; one ring and two double bonds; one ring and one triple bond; one double bond and one triple bond 
D)  three rings; two rings and a double bond; one ring and two double bonds; one ring and two triple bonds 
E)  two rings; two rings and a double bond; one ring and two double bonds; one ring and one triple bond

Question 14

Which of the following is TRUE regarding stereoisomers?

Accepted Answer

A)  Stereoisomers differ in the way atoms are connected but have identical spatial orientation of atoms. They can be conformational or configurational. 
B)  Stereoisomers differ in the way atoms are connected but have identical spatial orientation of atoms. They can be constitutional or configurational. 
C)  Stereoisomers have the same atom connectivity but have different spatial orientation of atoms. They can be constitutional or enantiomeric. 
D)  Stereoisomers have the same atom connectivity but have different spatial orientation of atoms. They can be conformational or configurational. 
E)  Stereoisomers have the same atom connectivity but have different functional groups on the same positions of the carbon backbone. They can be conformational or configurational. 
A)  Stereoisomers differ in the way atoms are connected but have identical spatial orientation of atoms. They can be conformational or configurational. 
B)  Stereoisomers differ in the way atoms are connected but have identical spatial orientation of atoms. They can be constitutional or configurational. 
C)  Stereoisomers have the same atom connectivity but have different spatial orientation of atoms. They can be constitutional or enantiomeric. 
D)  Stereoisomers have the same atom connectivity but have different spatial orientation of atoms. They can be conformational or configurational. 
E)  Stereoisomers have the same atom connectivity but have different functional groups on the same positions of the carbon backbone. They can be conformational or configurational.

Question 15

Which of the following statements is TRUE?

Accepted Answer

A)  Infrared absorption spectroscopy is a common method for identifying functional groups in the structure of organic molecules. 
B)  Infrared absorption spectroscopy is a technique that makes use of the fact that infrared photons can excite the valence electrons in organic molecules. 
C)  Infrared absorption spectroscopy is a simple yet powerful method for determining the absolute configuration of chiral organic molecules. 
D)  Infrared absorption spectroscopy observes the energy emitted by vibrating bonds in molecules. 
E)  Infrared absorption spectroscopy is a technique frequently used in separation of isomers. 
A)  Infrared absorption spectroscopy is a common method for identifying functional groups in the structure of organic molecules. 
B)  Infrared absorption spectroscopy is a technique that makes use of the fact that infrared photons can excite the valence electrons in organic molecules. 
C)  Infrared absorption spectroscopy is a simple yet powerful method for determining the absolute configuration of chiral organic molecules. 
D)  Infrared absorption spectroscopy observes the energy emitted by vibrating bonds in molecules. 
E)  Infrared absorption spectroscopy is a technique frequently used in separation of isomers.

Question 16

Which of the following statements is TRUE?

Accepted Answer

A)  A common reference compound for 1H and 13C NMR is tetramethylmethane. 
B)  Nuclear magnetic resonance spectroscopy uses the fact that some atomic nuclei, such as 1H and 13C, have two nuclear spin states with different energies under an applied magnetic field. 
C)  The energy difference between two nuclear spin states corresponds to the energy of photons in the microwave part of the electromagnetic spectrum. 
D)  The energy difference between two nuclear spin states depends on the number of protons and neutrons in the atomic nucleus. 
E)  The difference in absorption frequency of a nucleus outside the magnetic field and a nucleus inside the external magnetic field is called the chemical shift. 
A)  A common reference compound for 1H and 13C NMR is tetramethylmethane. 
B)  Nuclear magnetic resonance spectroscopy uses the fact that some atomic nuclei, such as 1H and 13C, have two nuclear spin states with different energies under an applied magnetic field. 
C)  The energy difference between two nuclear spin states corresponds to the energy of photons in the microwave part of the electromagnetic spectrum. 
D)  The energy difference between two nuclear spin states depends on the number of protons and neutrons in the atomic nucleus. 
E)  The difference in absorption frequency of a nucleus outside the magnetic field and a nucleus inside the external magnetic field is called the chemical shift.

Question 17

Which of the following acyclic compounds is an alkyne with one triple bond in its structure?

Accepted Answer

A)  C10H22 
B)  C11H22 
C)  C12H22 
D)  C9H18 
E)  C5H10 
A)  C10H22 
B)  C11H22 
C)  C12H22 
D)  C9H18 
E)  C5H10

Question 18

Which of the following structures shows a primary amine?

Accepted Answer

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

Question 19

Which of the following compounds is a ketone?

Accepted Answer

A)  CH3CH2CH2CO2H 
B)    
C)  CH3CH2NH2 
D)    
E)    
A)  CH3CH2CH2CO2H 
B)    
C)  CH3CH2NH2 
D)    
E)

Question 20

Which of the following alcohols has the lowest solubility in water?

Accepted Answer

A)  CH3CH2OH 
B)  CH3CH2CH2CH2OH 
C)  CH3CH2CH2CH2CH2OH 
D)  CH3CH2CH2CH2CH2CH2OH 
E)  CH3CH2CH2CH2CH2CH2CH2CH2OH 
A)  CH3CH2OH 
B)  CH3CH2CH2CH2OH 
C)  CH3CH2CH2CH2CH2OH 
D)  CH3CH2CH2CH2CH2CH2OH 
E)  CH3CH2CH2CH2CH2CH2CH2CH2OH

Exam 20: Organic Chemistry I: Structures

Find the correct statement about cis-trans isomers.

Which of the following lists the substituents in the order of priority, from highest (priority 1) to lowest (priority 4)?

Match the following. -

Which of the following compounds exhibit cis-trans isomerism?

Which of the following compounds is an alcohol?

Which of the following condensed general formulas represents tertiary alcohols?

Identify hybridization of carbon atoms numbered 1-6 in the structure below:

Determine the absolute configuration of the molecule shown below:

The infrared spectrum of a compound with molecular formula C6H8O has weak peaks around 1650 cm-1 and a strong peak around 1775 cm-1. What is the most likely structure of this compound?

Which of the following pairs of organic compound families could have constitutional isomers?

Explain the concept of bond polarization and inductive effect using organic halides as an example.

Find the correct Newman projection formula showing a staggered conformer of n-hexane.

What are the possible combinations of multiple bonds and rings if a compound's index of hydrogen deficiency equals 3?

Which of the following is TRUE regarding stereoisomers?

Which of the following statements is TRUE?

Which of the following statements is TRUE?

Which of the following acyclic compounds is an alkyne with one triple bond in its structure?

Which of the following structures shows a primary amine?

Which of the following compounds is a ketone?

Which of the following alcohols has the lowest solubility in water?

Units of Measurement for Physical and Chemical Change

Atoms and Elements

Molecules, Compounds, and Nomenclature

Chemical Reactions and Stoichiometry

Gases

Thermochemistry

The Quantum-Mechanical Model of the Atom

Periodic Properties of the Elements

Chemical Bonding I: Lewis Theory

Chemical Bonding Ii: Molecular Shapes, Valence Bond Theory, and Molecular Orbital Theory

Liquids, Solids, and Intermolecular Forces

Solutions

Chemical Kinetics

Chemical Equilibrium

Acids and Bases

Aqueous Ionic Equilibrium

Gibbs Energy and Thermodynamics

Electrochemistry

Radioactivity and Nuclear Chemistry

Organic Chemistry Ii: Reactions

Biochemistry

Chemistry of the Nonmetals

Metals and Metallurgy

Transition Metals and Coordination Compounds

Filters

The infrared spectrum of a compound with molecular formula C₆H₈O has weak peaks around 1650 cm^-1 and a strong peak around 1775 cm^-1. What is the most likely structure of this compound?