Question 1

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 2

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 3

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 4

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

Accepted Answer

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

Question 5

Which of the following statements is TRUE?

Accepted Answer

A) A common reference compound for 1H and 13C NMR is tetramethylsilane. 
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 when exposed to a high potential difference. 
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 tetramethylsilane. 
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 when exposed to a high potential difference. 
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 6

Which of the following compounds is an aldehyde?

Accepted Answer

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

Question 7

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 8

Which of the following structures shows a secondary amine?

Accepted Answer

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

Question 9

Which two functional groups combined give the functional group found in carboxylic acids?

Accepted Answer

A) carbonyl and hydroxyl 
B) carbonyl and amine 
C) ether and hydroxyl 
D) ester and hydroxyl 
E) chlorido and carbonyl 
A) carbonyl and hydroxyl 
B) carbonyl and amine 
C) ether and hydroxyl 
D) ester and hydroxyl 
E) chlorido and carbonyl

Question 10

Which of the following condensed general formulas represents ethers?

Accepted Answer

A) ROR 
B) RCOR 
C) RCHO 
D) ROH 
E) RCOOH 
A) ROR 
B) RCOR 
C) RCHO 
D) ROH 
E) RCOOH

Question 11

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

Question 12

Which of the following structures are constitutional isomers of a compound with molecular formula C4H9N?

Accepted Answer

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

Question 13

Which one of the following molecules is the most polar?

Accepted Answer

A) butane 
B) acetic acid 
C) cyclohexane 
D) methanol 
E) cyclohexanone 
A) butane 
B) acetic acid 
C) cyclohexane 
D) methanol 
E) cyclohexanone

Question 14

What is the difference between primary, secondary, and tertiary amines?

Accepted Answer

Amines can be considered a derivative of

Question 15

What are functional groups and how are they related to the concept of organic families? Provide examples.

Accepted Answer

A functional group is a characteristic a

Question 16

Which of the following is a tertiary alcohol?

Accepted Answer

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

Question 17

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 18

Explain the formation of triple bonds in alkynes. Make sure to mention the hybridization of carbon atoms.

Accepted Answer

The C-C triple bond is made of one σ and

Question 19

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 20

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

Exam 20: Organic Chemistry I: Structures

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

Which of the following statements is TRUE?

Which of the following statements is TRUE?

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

Which of the following statements is TRUE?

Which of the following compounds is an aldehyde?

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

Which of the following structures shows a secondary amine?

Which two functional groups combined give the functional group found in carboxylic acids?

Which of the following condensed general formulas represents ethers?

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

Which of the following structures are constitutional isomers of a compound with molecular formula C4H9N?

Which one of the following molecules is the most polar?

What is the difference between primary, secondary, and tertiary amines?

What are functional groups and how are they related to the concept of organic families? Provide examples.

Which of the following is a tertiary alcohol?

Which of the following condensed general formulas represents tertiary alcohols?

Explain the formation of triple bonds in alkynes. Make sure to mention the hybridization of carbon atoms.

Which of the following compounds exhibit cis-trans isomerism?

Determine the absolute configuration of the molecule shown below:

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

Which of the following structures are constitutional isomers of a compound with molecular formula C₄H₉N?