Question 1

Choose the best configuration assignments for the three double bonds, labeled A, B and C, in the following compound:

Accepted Answer

A)  A is trans, B is trans, and C is Z 
B)  A is cis, B is cis, and C is Z 
C)  A is trans, B is trans, and C is E 
D)  A is trans, B is trans, and C is cis 
E)  A is trans, B is trans, and C is trans 
A)  A is trans, B is trans, and C is Z 
B)  A is cis, B is cis, and C is Z 
C)  A is trans, B is trans, and C is E 
D)  A is trans, B is trans, and C is cis 
E)  A is trans, B is trans, and C is trans

Question 2

Give the name for (CH3)3CCHO.

Accepted Answer

A)  2, 2-dimethylpropanone 
B)  2-methylbutanol 
C)  1, 1, 1-trimethylethanol 
D)  2, 2-dimethylpropanal 
E)  ethylethanol 
A)  2, 2-dimethylpropanone 
B)  2-methylbutanol 
C)  1, 1, 1-trimethylethanol 
D)  2, 2-dimethylpropanal 
E)  ethylethanol

Question 3

A solid wedge line denotes a bond that sticks back behind the plane of the paper.

Accepted Answer

A) True 
 B)False

Question 4

What is the degree of unsaturation for the following compounds?

Accepted Answer

A)  For A the degree of unsaturation is 1, for B is 6 and for C is 5. 
B)  For A the degree of unsaturation is 1, for B is 5 and for C is 6. 
C)  For A the degree of unsaturation is 0, for B is 6 and for C is 5. 
D)  For A the degree of unsaturation is 1, for B is 6 and for C is 4. 
E)  For A the degree of unsaturation is 1, for B is 4 and for C is 5. 
A)  For A the degree of unsaturation is 1, for B is 6 and for C is 5. 
B)  For A the degree of unsaturation is 1, for B is 5 and for C is 6. 
C)  For A the degree of unsaturation is 0, for B is 6 and for C is 5. 
D)  For A the degree of unsaturation is 1, for B is 6 and for C is 4. 
E)  For A the degree of unsaturation is 1, for B is 4 and for C is 5.

Question 5

The two benzene substituents of the common analgesic shown below are considered in what relation to one another?

Accepted Answer

A)  ortho 
B)  para 
C)  meta 
D)  trans 
E)  1,3 
A)  ortho 
B)  para 
C)  meta 
D)  trans 
E)  1,3

Question 6

How many skeletal isomers for C6H14 can be drawn?

Accepted Answer

A)  6 
B)  3 
C)  8 
D)  5 
E)  2 
A)  6 
B)  3 
C)  8 
D)  5 
E)  2

Question 7

Constitutional isomers have different bond connectivities, and as a consequence they have different skeletal structures.

Accepted Answer

A) True 
 B)False

Question 8

Which of the following has the lowest melting point: cyclohexane, hexane, benzene?

Accepted Answer

A)  cyclohexane 
B)  hexane 
C)  benzene 
D)  They have approximately the same melting point. 
E)  There is not enough information to determine. 
A)  cyclohexane 
B)  hexane 
C)  benzene 
D)  They have approximately the same melting point. 
E)  There is not enough information to determine.

Question 9

How many different structural isomers are there of the compound dichlorobutane?

Accepted Answer

A)  6 
B)  8 
C)  9 
D)  5 
E)  7 
A)  6 
B)  8 
C)  9 
D)  5 
E)  7

Question 10

Which class of compounds is most oxidized?

Accepted Answer

A)  alkanes 
B)  alcohols 
C)  acids 
D)  aldehydes 
E)  ketones 
A)  alkanes 
B)  alcohols 
C)  acids 
D)  aldehydes 
E)  ketones

Question 11

Can 1,3,5-hexatriene be considered an aromatic compound? Why do you think so?

Accepted Answer

A)  Yes, because it contains alternating double and single bonds. 
B)  No, because the molecule is not a flat ring. 
C)  Yes, because its double bonds contain 4n+2 electrons (n = 1). 
D)  No, because the structure is not based on benzene ring. 
E)  Yes, because the molecule has a delocalized π electron cloud. 
A)  Yes, because it contains alternating double and single bonds. 
B)  No, because the molecule is not a flat ring. 
C)  Yes, because its double bonds contain 4n+2 electrons (n = 1). 
D)  No, because the structure is not based on benzene ring. 
E)  Yes, because the molecule has a delocalized π electron cloud.

Question 12

Define "conformation".

Accepted Answer

A)  Conformations are different arrangements of bonds in space 
B)  Conformations are different structural representations of the same molecule. 
C)  Conformations are different spatial arrangements one structure can have 
D)  Conformations are two enantiomers. 
E)  Conformations are all possible structural isomers for a given molecular formula 
A)  Conformations are different arrangements of bonds in space 
B)  Conformations are different structural representations of the same molecule. 
C)  Conformations are different spatial arrangements one structure can have 
D)  Conformations are two enantiomers. 
E)  Conformations are all possible structural isomers for a given molecular formula

Question 13

What is the correct IUPAC name for the following structure?

Accepted Answer

A)  2-ethyl-3- methylheptane 
B)  3, 5 - dimethyloctane 
C)  4-methyl-6-ethylheptane 
D)  4, 6 - dimethyloctane 
E)  3, 5 - dimethyloctyl 
A)  2-ethyl-3- methylheptane 
B)  3, 5 - dimethyloctane 
C)  4-methyl-6-ethylheptane 
D)  4, 6 - dimethyloctane 
E)  3, 5 - dimethyloctyl

Question 14

Compound A easily reacts with water to give compound B. Compound B on the other hand can be oxidized to produce compound C. Both B and C can be further oxidized to produce D. To which classes of organic compounds A, B, C and D most likely belong?

Accepted Answer

A)  A is an alkane, B is an alcohol, C is an aldehyde and D is a carboxylic acid 
B)  A is an alkene, B is an ether, C is an aldehyde and D is a carboxylic acid 
C)  A is an alkene, B is an alcohol, C is a ketone and D is a carboxylic acid 
D)  A is an alkene, B is an alcohol, C is an aldehyde and D is an ester 
E)  A is an alkene, B is an alcohol, C is an aldehyde and D is a carboxylic acid 
A)  A is an alkane, B is an alcohol, C is an aldehyde and D is a carboxylic acid 
B)  A is an alkene, B is an ether, C is an aldehyde and D is a carboxylic acid 
C)  A is an alkene, B is an alcohol, C is a ketone and D is a carboxylic acid 
D)  A is an alkene, B is an alcohol, C is an aldehyde and D is an ester 
E)  A is an alkene, B is an alcohol, C is an aldehyde and D is a carboxylic acid

Question 15

What is the complete systematic name for the following molecule?

Accepted Answer

A)  3-pentene 
B)  3-hexene 
C)  cis-3-hexene 
D)  trans-3-hexene 
E)  cis-3-hexyne 
A)  3-pentene 
B)  3-hexene 
C)  cis-3-hexene 
D)  trans-3-hexene 
E)  cis-3-hexyne

Question 16

Give the name for CH3CH2CHBrCH3.

Accepted Answer

A)  2-bromobutane 
B)  3-bromobutane 
C)  2-bromopropane 
D)  3-bromopropane 
E)  3-bromylpentane 
A)  2-bromobutane 
B)  3-bromobutane 
C)  2-bromopropane 
D)  3-bromopropane 
E)  3-bromylpentane

Question 17

Which of the following five positions would result in the most stable molecule for a large group like t-butyl, -C(CH3)3?

Accepted Answer

A)  equatorial position in boat cyclohexane 
B)  axial position in boat cyclohexane 
C)  two or more of these answers are equally stable 
D)  axial position in chair cyclohexane 
E)  equatorial position in chair cyclohexane 
A)  equatorial position in boat cyclohexane 
B)  axial position in boat cyclohexane 
C)  two or more of these answers are equally stable 
D)  axial position in chair cyclohexane 
E)  equatorial position in chair cyclohexane

Question 18

Calculate the degree of unsaturation for the molecule below:

Accepted Answer

A)  3 
B)  5 
C)  7 
D)  9 
E)  11 
A)  3 
B)  5 
C)  7 
D)  9 
E)  11

Question 19

Give the name for CH3CH2CH2COCH2CH3.

Accepted Answer

A)  4-hexanone 
B)  3-hexanone 
C)  3-butanone 
D)  3-hexanol 
E)  4-hexanoic acid 
A)  4-hexanone 
B)  3-hexanone 
C)  3-butanone 
D)  3-hexanol 
E)  4-hexanoic acid

Question 20

The burning of alkanes to produce carbon dioxide and water is known as what type of reaction?

Accepted Answer

A)  thermal cracking 
B)  reforming 
C)  radical substitution 
D)  oxidation 
E)  alkylation 
A)  thermal cracking 
B)  reforming 
C)  radical substitution 
D)  oxidation 
E)  alkylation

Exam 26: Structures of Organic Compounds

Choose the best configuration assignments for the three double bonds, labeled A, B and C, in the following compound:

Give the name for (CH3)3CCHO.

A solid wedge line denotes a bond that sticks back behind the plane of the paper.

What is the degree of unsaturation for the following compounds?

The two benzene substituents of the common analgesic shown below are considered in what relation to one another?

How many skeletal isomers for C6H14 can be drawn?

Constitutional isomers have different bond connectivities, and as a consequence they have different skeletal structures.

Which of the following has the lowest melting point: cyclohexane, hexane, benzene?

How many different structural isomers are there of the compound dichlorobutane?

Which class of compounds is most oxidized?

Can 1,3,5-hexatriene be considered an aromatic compound? Why do you think so?

Define "conformation".

What is the correct IUPAC name for the following structure?

Compound A easily reacts with water to give compound B. Compound B on the other hand can be oxidized to produce compound C. Both B and C can be further oxidized to produce D. To which classes of organic compounds A, B, C and D most likely belong?

What is the complete systematic name for the following molecule?

Give the name for CH3CH2CHBrCH3.

Which of the following five positions would result in the most stable molecule for a large group like t-butyl, -C(CH3)3?

Calculate the degree of unsaturation for the molecule below:

Give the name for CH3CH2CH2COCH2CH3.

The burning of alkanes to produce carbon dioxide and water is known as what type of reaction?

Matter - Its Properties and Measurement

Atoms and the Atomic Theory

Chemical Compounds

Chemical Reactions

Introduction to Reactions in Aqueous Solutions

Gases

Thermochemistry

Electrons in Atoms

The Periodic Table and Some Atomic Properties

Chemical Bonding I: Basic Concepts

Chemical Bonding II: Additional Aspects

Intermolecular Forces: Liquids and Solids

Solutions and Their Physical Properties

Chemical Kinetics

Principles of Chemical Equilibrium

Acids and Bases

Additional Aspects of Acid-Base Equilibria

Solubility and Complex-Ion Equilibria

Spontaneous Change: Entropy and Free Energy

Electrochemistry

Main Group Elements I: Groups 1, 2, 13, and 14

Main Group Elements II: Groups 18, 17, 16, 15, and Hydrogen

The Transition Elements

Complex Ions and Coordination Compounds

Nuclear Chemistry 1-41

Reactions of Organic Compounds

Chemistry of the Living State

Filters

Give the name for (CH₃)₃CCHO.

How many skeletal isomers for C₆H₁₄ can be drawn?

Give the name for CH₃CH₂CHBrCH₃.

Which of the following five positions would result in the most stable molecule for a large group like t-butyl, -C(CH₃)₃?

Give the name for CH₃CH₂CH₂COCH₂CH₃.