Question 1

Which of the following compounds is an alcohol?

Accepted Answer

A) CH3CH2CH2CO2H 
B) CH3-O-CH3 
C) CH3CO2CH3 
D) CH3CH2CH=O 
E) CH2OH-CH2OH 
A) CH3CH2CH2CO2H 
B) CH3-O-CH3 
C) CH3CO2CH3 
D) CH3CH2CH=O 
E) CH2OH-CH2OH E

Question 2

What are the possible combinations of multiple bonds and rings if a compound's index of hydrogen deficiency equals 2?

Accepted Answer

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

Question 3

Identify the generic formula for alkanes.

Accepted Answer

A) CnH2n+2 
B) CnH2n-2 
C) CnH2n 
D) CnH2n-4 
E) CnH2n+4 
A) CnH2n+2 
B) CnH2n-2 
C) CnH2n 
D) CnH2n-4 
E) CnH2n+4 A

Question 4

Which of the following functional groups is found in amines?

Accepted Answer

A) -C≡N 
B) -NO2 
C) -NH2 
D) -N≡N 
E) -N=NH 
A) -C≡N 
B) -NO2 
C) -NH2 
D) -N≡N 
E) -N=NH

Question 5

Which of the following compounds is chiral?

Accepted Answer

A) 3-methylhexane 
B) 3-ethylhexane 
C) 2-methylhexane 
D) 4-ethylheptane 
E) 3-ethylpentane 
A) 3-methylhexane 
B) 3-ethylhexane 
C) 2-methylhexane 
D) 4-ethylheptane 
E) 3-ethylpentane

Question 6

Which of the following pairs are constitutional isomers?

Accepted Answer

A) CH3CH=CHCH2OH and CH3CH=CHOCH3 
B) ClCH2CH2CH2CH3 and CH3CH2CH2CH2Cl 
C) CH3CH(OH)CH2CH3 and CH3CH2(HO)CHCH3 
D) H2NCH2CH=CHCOOH and HOOCCH=CH(H2N)CH2 
E) CH3OCH2CH2CH2CH3 and CH3OCH2CH2CH2OCH3 
A) CH3CH=CHCH2OH and CH3CH=CHOCH3 
B) ClCH2CH2CH2CH3 and CH3CH2CH2CH2Cl 
C) CH3CH(OH)CH2CH3 and CH3CH2(HO)CHCH3 
D) H2NCH2CH=CHCOOH and HOOCCH=CH(H2N)CH2 
E) CH3OCH2CH2CH2CH3 and CH3OCH2CH2CH2OCH3

Question 7

Which of the following alcohols has the highest 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

Question 8

What is the index of hydrogen deficiency in C9H16Br2?

Accepted Answer

A) 5 
B) 4 
C) 3 
D) 2 
E) 1 
A) 5 
B) 4 
C) 3 
D) 2 
E) 1

Question 9

Which of the following acyclic compounds is an alkene with one double bond in its structure?

Accepted Answer

A) C10H22 
B) C11H22 
C) C12H22 
D) C6H10 
E) C5H8 
A) C10H22 
B) C11H22 
C) C12H22 
D) C6H10 
E) C5H8

Question 10

Which of the following compounds is ethanol?

Accepted Answer

A) C2H6 
B) C2H5OH 
C) CH3CO2H 
D) CH3CO2CH3 
E) CH3-O-CH3 
A) C2H6 
B) C2H5OH 
C) CH3CO2H 
D) CH3CO2CH3 
E) CH3-O-CH3

Question 11

Which of the bold and underlined carbon atoms would be the most shielded in 13C NMR?

Accepted Answer

A) H3C-OH 
B) CH3CH2NH2 
C) HCOOH 
D) CH3CH2OCH2CH3 
E) CH3C(=O)H 
A) H3C-OH 
B) CH3CH2NH2 
C) HCOOH 
D) CH3CH2OCH2CH3 
E) CH3C(=O)H

Question 12

Which of the following Newman projections shows an antistaggered conformation of n-pentane?

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 
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 
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

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 15

Which of the following statements regarding functional groups and families is TRUE?

Accepted Answer

A) A group of organic compounds forms a family if they share the same characteristic carbon atom backbone called the functional group. 
B) A group of organic compounds forms a family if they share the same characteristic atom or a group of atoms called the functional group. 
C) A group of organic compounds forms a family if they differ by one CH group, called the functional group, in their structure. 
D) A family of organic compounds are all structural isomers with the same molecular formula called the functional group formula. 
E) A family of organic compounds is composed of all isomers that have the same molecular formula and share the same characteristic atom or a group of atoms called the functional group. 
A) A group of organic compounds forms a family if they share the same characteristic carbon atom backbone called the functional group. 
B) A group of organic compounds forms a family if they share the same characteristic atom or a group of atoms called the functional group. 
C) A group of organic compounds forms a family if they differ by one CH group, called the functional group, in their structure. 
D) A family of organic compounds are all structural isomers with the same molecular formula called the functional group formula. 
E) A family of organic compounds is composed of all isomers that have the same molecular formula and share the same characteristic atom or a group of atoms called the functional group.

Question 16

Which one of the following structures belongs to the amide family?

Accepted Answer

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

Question 17

How many of the carbons in the following compound are chiral centre(s)?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 or more 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4 or more

Question 18

Which of the following compounds is an ether?

Accepted Answer

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

Question 19

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

Accepted Answer

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

Question 20

What is the index of hydrogen deficiency in C20H32?

Accepted Answer

A) 5 
B) 4 
C) 3 
D) 2 
E) 1 
A) 5 
B) 4 
C) 3 
D) 2 
E) 1

Exam 20: Organic Chemistry I: Structures

Which of the following compounds is an alcohol?

What are the possible combinations of multiple bonds and rings if a compound's index of hydrogen deficiency equals 2?

Identify the generic formula for alkanes.

Which of the following functional groups is found in amines?

Which of the following compounds is chiral?

Which of the following pairs are constitutional isomers?

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

What is the index of hydrogen deficiency in C9H16Br2?

Which of the following acyclic compounds is an alkene with one double bond in its structure?

Which of the following compounds is ethanol?

Which of the bold and underlined carbon atoms would be the most shielded in 13C NMR?

Which of the following Newman projections shows an antistaggered conformation of n-pentane?

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

Find the correct statement about cis-trans isomers.

Which of the following statements regarding functional groups and families is TRUE?

Which one of the following structures belongs to the amide family?

How many of the carbons in the following compound are chiral centre(s)?

Which of the following compounds is an ether?

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

What is the index of hydrogen deficiency in C20H32?

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 Metallury

Transition Metals and Coordination Compounds

Filters

What is the index of hydrogen deficiency in C₉H₁₆Br₂?

Which of the bold and underlined carbon atoms would be the most shielded in ¹³C NMR?

What is the index of hydrogen deficiency in C₂₀H₃₂?