Question 1

Which of the following is TRUE regarding constitutional isomers?

Accepted Answer

A) Constitutional isomers have the same molecular formula but different structures,physical,and chemical properties. 
B) Constitutional isomers have the same molecular formula and physical properties but different structures and chemical properties. 
C) Constitutional isomers have the same molecular formula,physical,and chemical properties but different structures. 
D) Constitutional isomers have the same chemical structure and molecular formula but different physical and chemical properties. 
E) Constitutional isomers have the same chemical structure but different formulas,physical,and chemical properties. 
A) Constitutional isomers have the same molecular formula but different structures,physical,and chemical properties. 
B) Constitutional isomers have the same molecular formula and physical properties but different structures and chemical properties. 
C) Constitutional isomers have the same molecular formula,physical,and chemical properties but different structures. 
D) Constitutional isomers have the same chemical structure and molecular formula but different physical and chemical properties. 
E) Constitutional isomers have the same chemical structure but different formulas,physical,and chemical properties.

Question 2

Which of the following have correct assignments of both group priorities and absolute configurations?

Accepted Answer

A) 
  ,R configuration 
B) 
  ,S configuration 
C) 
  ,S configuration 
D) 
  ,l configuration 
E) 
  ,d configuration 
A) 
  ,R configuration 
B) 
  ,S configuration 
C) 
  ,S configuration 
D) 
  ,l configuration 
E) 
  ,d configuration

Question 3

Determine the absolute configuration of the molecule shown below:

Accepted Answer

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

Question 4

When does conjugation occur?

Accepted Answer

A) Conjugation occurs every time an organic molecule has a heteroatom in its structure regardless of hybridization. 
B) Conjugation occurs every time an organic molecule has a sequence of three or more sp2 hybridized atoms. 
C) Conjugation occurs every time an organic molecule has a sequence of three or more sp3 hybridized atoms. 
D) Conjugation occurs every time an organic molecule has a sequence of two or more sp2 hybridized atoms. 
E) Conjugation occurs every time an organic molecule has a ring-type structure. 
A) Conjugation occurs every time an organic molecule has a heteroatom in its structure regardless of hybridization. 
B) Conjugation occurs every time an organic molecule has a sequence of three or more sp2 hybridized atoms. 
C) Conjugation occurs every time an organic molecule has a sequence of three or more sp3 hybridized atoms. 
D) Conjugation occurs every time an organic molecule has a sequence of two or more sp2 hybridized atoms. 
E) Conjugation occurs every time an organic molecule has a ring-type structure.

Question 5

What does the term "racemic mixture" mean?

Accepted Answer

A mixture (equal in mole ratio

Question 6

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

Accepted Answer

Halogen atoms are more electronegative t

Question 7

Which of the following statements correctly describes organic halides?

Accepted Answer

A) Organic halides have one or more H atoms substituted by an electronegative atom from group 16 of the periodic table. 
B) Organic halides have one or more C atoms substituted by an electronegative atom from group 17 of the periodic table. 
C) Organic halides have one or more H atoms substituted by an electronegative atom from group 17 of the periodic table. 
D) Organic halides have one or more H atoms substituted by an electropositive atom from group 17 of the periodic table. 
E) Organic halides have one or more H atoms substituted by an electronegative atom from group 7 of the periodic table. 
A) Organic halides have one or more H atoms substituted by an electronegative atom from group 16 of the periodic table. 
B) Organic halides have one or more C atoms substituted by an electronegative atom from group 17 of the periodic table. 
C) Organic halides have one or more H atoms substituted by an electronegative atom from group 17 of the periodic table. 
D) Organic halides have one or more H atoms substituted by an electropositive atom from group 17 of the periodic table. 
E) Organic halides have one or more H atoms substituted by an electronegative atom from group 7 of the periodic table.

Question 8

Which of the bold and underlined carbon atoms would be the most deshielded 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 9

What is the index of hydrogen deficiency in C10H12N2O3?

Accepted Answer

A) 5 
B) 4 
C) 3 
D) 2 
E) 6 
A) 5 
B) 4 
C) 3 
D) 2 
E) 6

Question 10

Determine the absolute configuration of the molecule shown below:

Accepted Answer

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

Question 11

Determine the absolute configuration of the molecule shown below:

Accepted Answer

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

Question 12

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

Question 13

Which of the following structures shows a secondary amine?

Accepted Answer

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

Question 14

Which of the following structures shows a Z alkene isomer?

Accepted Answer

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

Question 15

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 16

Which of the following Newman projections shows a staggered conformer of 2-methyl-butane?

Accepted Answer

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

Question 17

Which of the following statements is TRUE?

Accepted Answer

A) Optical activity describes the property of a chiral compound to rotate the plane of polarized light. 
B) Two enantiomers differ significantly in physical properties.This difference is the basis for the separation of the two enantiomers from a racemic mixture. 
C) A racemic mixture is an optically active mixture of two enantiomers. 
D) It is possible to determine if an enantiomer is the levorotary or dextrorotary isomer by analyzing its infrared spectrum. 
E) If an enantiomer has an S absolute configuration then it must be the levorotary isomer. 
A) Optical activity describes the property of a chiral compound to rotate the plane of polarized light. 
B) Two enantiomers differ significantly in physical properties.This difference is the basis for the separation of the two enantiomers from a racemic mixture. 
C) A racemic mixture is an optically active mixture of two enantiomers. 
D) It is possible to determine if an enantiomer is the levorotary or dextrorotary isomer by analyzing its infrared spectrum. 
E) If an enantiomer has an S absolute configuration then it must be the levorotary isomer.

Question 18

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 19

Which of the following structures are enantiomers?

Accepted Answer

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

Question 20

Which of the following is a secondary alcohol?

Accepted Answer

A) CH3CH2OH 
B) (CH3)2(CH3CH2)COH 
C) (CH3)3COH 
D) (CH3)2CHCH(CH3)OH 
E) CH3OCH3 
A) CH3CH2OH 
B) (CH3)2(CH3CH2)COH 
C) (CH3)3COH 
D) (CH3)2CHCH(CH3)OH 
E) CH3OCH3

Exam 20: Organic Chemistry I: Structures

Which of the following is TRUE regarding constitutional isomers?

Which of the following have correct assignments of both group priorities and absolute configurations?

Determine the absolute configuration of the molecule shown below:

When does conjugation occur?

What does the term "racemic mixture" mean?

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

Which of the following statements correctly describes organic halides?

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

What is the index of hydrogen deficiency in C10H12N2O3?

Determine the absolute configuration of the molecule shown below:

Determine the absolute configuration of the molecule shown below:

What is the index of hydrogen deficiency in C20H32?

Which of the following structures shows a secondary amine?

Which of the following structures shows a Z alkene isomer?

What is the index of hydrogen deficiency in C9H16Br2?

Which of the following Newman projections shows a staggered conformer of 2-methyl-butane?

Which of the following statements is TRUE?

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

Which of the following structures are enantiomers?

Which of the following is a secondary alcohol?

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

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

What is the index of hydrogen deficiency in C₁₀H₁₂N₂O₃?

What is the index of hydrogen deficiency in C₂₀H₃₂?

What is the index of hydrogen deficiency in C₉H₁₆Br₂?