Question 1

What is the correct IUPAC name for the following molecule?

Accepted Answer

A)  6-propyl-5,7,8-trimethyldecane 
B)  5,7,8-trimethyl-6-propyldecane 
C)  3,4,6-trimethyl-5-propyldecane 
D)  5-propyl-3,4,6-trimethyldecane 
E)  None of the above. 
A)  6-propyl-5,7,8-trimethyldecane 
B)  5,7,8-trimethyl-6-propyldecane 
C)  3,4,6-trimethyl-5-propyldecane 
D)  5-propyl-3,4,6-trimethyldecane 
E)  None of the above. C

Question 2

Name the following functional group:

Accepted Answer

A)  ester 
B)  ketone 
C)  alcohol 
D)  carboxylic acid 
E)  anhydride 
A)  ester 
B)  ketone 
C)  alcohol 
D)  carboxylic acid 
E)  anhydride E

Question 3

Consider the potential energy diagram for rotation about the C2-C3 bond in pentane.The position marked "A" most likely corresponds to which of the following Newman projections?

Accepted Answer

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

Question 4

The IUPAC name for [(CH3)3C]2CHCH3 is:

Accepted Answer

A)  1,1-di-tert-butylethane 
B)  3-tert-butyl-2,2-dimethylbutane 
C)  2,2,3,4,4-pentamethylpentane 
D)  2,4,4-trimethylheptane 
E)  None of the above. 
A)  1,1-di-tert-butylethane 
B)  3-tert-butyl-2,2-dimethylbutane 
C)  2,2,3,4,4-pentamethylpentane 
D)  2,4,4-trimethylheptane 
E)  None of the above.

Question 5

All steroids are derivatives of the ring system shown.How many tertiary hydrogens are in this ring system?

Accepted Answer

A)  none 
B)  2 
C)  4 
D)  5 
E)  6 
A)  none 
B)  2 
C)  4 
D)  5 
E)  6

Question 6

Which of the following has the highest pKa?

Accepted Answer

A)  HI 
B)  NH3 
C)  HNO3 
D)  CH3COOH 
E)  H2SO4 
A)  HI 
B)  NH3 
C)  HNO3 
D)  CH3COOH 
E)  H2SO4

Question 7

The following represents what functional group?

Accepted Answer

A)  alcohol 
B)  aldehyde 
C)  carboxylic acid 
D)  amide 
E)  ketone 
A)  alcohol 
B)  aldehyde 
C)  carboxylic acid 
D)  amide 
E)  ketone

Question 8

What is the name given to the Newman projection of the butane conformation shown here?

Accepted Answer

A)  eclipsed 
B)  gauche 
C)  staggered 
D)  anti 
E)  skewed 
A)  eclipsed 
B)  gauche 
C)  staggered 
D)  anti 
E)  skewed

Question 9

The following represents what functional group?

Accepted Answer

A)  amide 
B)  thiol 
C)  ketone 
D)  nitrile 
E)  amine 
A)  amide 
B)  thiol 
C)  ketone 
D)  nitrile 
E)  amine

Question 10

What is the correct structure for tert-butyl bromide?

Accepted Answer

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

Question 11

Which of the following is considered to be a nucleophile?

Accepted Answer

A)  CH3Cl 
B)  CH3CH2I 
C) 
  
D) 
  
E) 
  
A)  CH3Cl 
B)  CH3CH2I 
C) 
  
D) 
  
E)

Question 12

What is the correct IUPAC name for the following molecule?

Accepted Answer

A)  1-ethyl-2-methylhexane 
B)  2-ethyl-1-methylcycloheptane 
C)  4-ethyl-5-methylcyclohexane 
D)  1-ethyl-2-methylcyclohexane 
E)  1-methyloctane 
A)  1-ethyl-2-methylhexane 
B)  2-ethyl-1-methylcycloheptane 
C)  4-ethyl-5-methylcyclohexane 
D)  1-ethyl-2-methylcyclohexane 
E)  1-methyloctane

Question 13

Arrange these acids in the order of increasing acidity.

Accepted Answer

A)  CH4,H2O,HF,NH3 
B)  HF,H2O,CH4,NH3 
C)  HF,H2O,NH3,CH4, 
D)  CH4,NH3,H2O,HF, 
E)  NH3,CH4,H2O,HF, 
A)  CH4,H2O,HF,NH3 
B)  HF,H2O,CH4,NH3 
C)  HF,H2O,NH3,CH4, 
D)  CH4,NH3,H2O,HF, 
E)  NH3,CH4,H2O,HF,

Question 14

How many ester functional groups are in the potent anticancer compound Taxol?

Accepted Answer

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

Question 15

Which isomer of C7H16 shown would have the highest boiling point?

Accepted Answer

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

Question 16

What is the name given to the Newman projection of the butane conformation shown here?

Accepted Answer

A)  anti 
B)  gauche 
C)  staggered 
D)  eclipsed 
E)  skewed 
A)  anti 
B)  gauche 
C)  staggered 
D)  eclipsed 
E)  skewed

Question 17

The following Newman projection represents which molecule?

Accepted Answer

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

Question 18

The following represents what functional group?

Accepted Answer

A)  ester 
B)  ether 
C)  alcohol 
D)  thiol 
E)  ketone 
A)  ester 
B)  ether 
C)  alcohol 
D)  thiol 
E)  ketone

Question 19

The correct name of the following molecule would be:

Accepted Answer

A)  2-ethyl-3,3-dimethylheptane 
B)  6-ethyl-5,5-dimethylheptane 
C)  3,4,4-trimethyloctane 
D)  2-butyl-3-methylpentane 
E)  2-sec-butyl-2-methylhexane 
A)  2-ethyl-3,3-dimethylheptane 
B)  6-ethyl-5,5-dimethylheptane 
C)  3,4,4-trimethyloctane 
D)  2-butyl-3-methylpentane 
E)  2-sec-butyl-2-methylhexane

Question 20

The following Newman projection corresponds to which molecule?

Accepted Answer

A)  pentane 
B)  butane 
C)  3-ethylbutane 
D)  hexane 
E)  3-methylpentane 
A)  pentane 
B)  butane 
C)  3-ethylbutane 
D)  hexane 
E)  3-methylpentane

Exam 2: Structure and Reactivity: Acids and Bases,polar and Nonpolar Molecules

What is the correct IUPAC name for the following molecule?

Name the following functional group:

Consider the potential energy diagram for rotation about the C2-C3 bond in pentane.The position marked "A" most likely corresponds to which of the following Newman projections?

The IUPAC name for [(CH3)3C]2CHCH3 is:

All steroids are derivatives of the ring system shown.How many tertiary hydrogens are in this ring system?

Which of the following has the highest pKa?

The following represents what functional group?

What is the name given to the Newman projection of the butane conformation shown here?

The following represents what functional group?

What is the correct structure for tert-butyl bromide?

Which of the following is considered to be a nucleophile?

What is the correct IUPAC name for the following molecule?

Arrange these acids in the order of increasing acidity.

How many ester functional groups are in the potent anticancer compound Taxol?

Which isomer of C7H16 shown would have the highest boiling point?

What is the name given to the Newman projection of the butane conformation shown here?

The following Newman projection represents which molecule?

The following represents what functional group?

The correct name of the following molecule would be:

The following Newman projection corresponds to which molecule?

Structure and Bonding in Organic Molecules

Reactions of Alkanes: Bond-Dissociation Energies,radical Halogenation,and Relative Reactivity

Cycloalkanes

Stereoisomers

Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution

Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Hydroxy of Functional Group: Alcohols: Properties,preparation,and Strategy of Synthesis

Further Reactions of Alcohols and the Chemistry of Ethers

Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure

Alkenes: Infrared Spectroscopy and Mass Spectrometry

Reactions to Alkenes

Alkynes: the Carbon

Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy Interlude

Benzene and Aromaticity: Electrophilic Aromatic Substitution

Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Aldehydes and Ketones: the Carbonyl Group

Enols,enolates,and the Aldol Condensation: A,b-Unsaturated Aldehydes and Ketones

Carboxylic Acids

Carboxylic Acid Derivatives

Amines and Their Derivatives: Functional Groups Containing Nitrogen

Chemistry of the Benzene Substituents: Alkylbenzenes,phenols,and Benzenamines

Ester Enolates and the Claisen Condensation: Synthesis of B-Dicarbonyl Compounds; Acyl Anion Equivalents

Carbohydrates: Polyfunctional Compounds in Nature

Heterocycles: Heteroatoms in Cyclic Organic Compounds

Amino Acids,peptides,proteins,and Nucleic Acids: Nitrogen-Containing Polymers in Nature

Filters

The IUPAC name for [(CH₃)₃C]₂CHCH₃ is:

Which isomer of C₇H₁₆ shown would have the highest boiling point?