Question 1

Cyclohexane has a molecular formula of C₆H₁₂ and an unsaturation number of 1. Is this compound considered to be unsaturated? Why or why not?

Accepted Answer

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Question 2

Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least heat upon hydrogenation)?

Accepted Answer

A)  2,3-dimethyl-2-butene 
B)  2-methyl-2-butene 
C)  trans-2-butene 
D)  cis-2-butene 
E)  1-hexene

Question 3

A newly isolated natural product was found to have the molecular formula C15H28O2. By hydrogenating a sample of the compound, it was determined to possess one π bond. How many rings are present in the compound?

Accepted Answer

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

Question 4

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

Accepted Answer

A)  1-chloropentane 
B)  2-chloropentane 
C)  3-chloropentane 
D)  1-chloro-2-methylbutane 
E)  1-chloro-3-methylbutane

Question 5

Provide a correct IUPAC name for the structure below.

Accepted Answer

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Question 6

Provide the proper IUPAC name for the alkene shown below. CH₂ CHCH₂CH₂CH₂CH₃

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Question 7

Carbon-carbon single bonds tend to be ________ and ________ than carbon-carbon double bonds.

Accepted Answer

A)  shorter; stronger 
B)  longer; stronger 
C)  shorter; weaker 
D)  longer; weaker

Question 8

Does the alkene shown below violate Bredt's rule?

Accepted Answer

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Question 9

Which sequence ranks the following compounds in order of increasing heat of hydrogenation, ΔHhyd?
1 cis-2-butene 2 1-butene 3 cyclohexene

Accepted Answer

A)  3<1<2 
B)  3<2<1 
C)  2<1<3 
D)  1<3<2

Question 10

Give the structures of three examples of molecules that have a molecular formula of C₆H₈. One of the structures should have only one ring and one of the structures should have no rings.

Accepted Answer

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Question 11

Name the compound shown below.

Accepted Answer

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Question 12

The carbon-carbon bond length in ethylene is ________ than the carbon-carbon bond length in ethane, and the HCH bond angle in ethylene is ________ the HCH bond angle in ethane.

Accepted Answer

A)  shorter; smaller than 
B)  shorter; larger than 
C)  longer; smaller than 
D)  longer; larger than 
E)  longer; the same as

Question 13

Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer.

Accepted Answer

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Question 14

The dehydrogenation of butane to trans-but-2-ene has ∆H° = +116 kJ/mol (+27.6 kcal/mol) and ∆S° = +117 J-kelvin/mol (+28.0 cal-kelvin/mol). Compute the value of ∆G° for dehydrogenation at room temperature (25°C or 298°K). Is dehydrogenation favored or disfavored?

Accepted Answer

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Question 15

Circle the most stable alkene in the set of isomers below.

Accepted Answer

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Question 16

Draw the alkene of formula C₅H₁₀which evolves the most heat per mole upon hydrogenation.

Accepted Answer

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Question 17

The steroid testosterone has the molecular formula C19H28O2. Given that there are two π bonds in a molecule of testosterone, how many rings are present in each molecule?

Accepted Answer

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

Question 18

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Accepted Answer

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Question 19

Draw a mechanism and use a chair structure to explain the major product that is formed in the reaction below.

Accepted Answer

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Question 20

Provide the proper IUPAC name for the alkene shown below.

Accepted Answer

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Exam 7: Structure and Synthesis of Alkenes; Elimination

Cyclohexane has a molecular formula of C₆H₁₂ and an unsaturation number of 1. Is this compound considered to be unsaturated? Why or why not?

Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least heat upon hydrogenation) ?

A newly isolated natural product was found to have the molecular formula C₁₅H₂₈O₂. By hydrogenating a sample of the compound, it was determined to possess one π bond. How many rings are present in the compound?

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

Provide a correct IUPAC name for the structure below.

Provide the proper IUPAC name for the alkene shown below. CH₂ CHCH₂CH₂CH₂CH₃

Carbon-carbon single bonds tend to be and than carbon-carbon double bonds.

Does the alkene shown below violate Bredt's rule?

Which sequence ranks the following compounds in order of increasing heat of hydrogenation, ΔH_hyd? 1 cis-2-butene 2 1-butene 3 cyclohexene

Give the structures of three examples of molecules that have a molecular formula of C₆H₈. One of the structures should have only one ring and one of the structures should have no rings.

Name the compound shown below.

The carbon-carbon bond length in ethylene is than the carbon-carbon bond length in ethane, and the HCH bond angle in ethylene is the HCH bond angle in ethane.

Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer.

The dehydrogenation of butane to trans-but-2-ene has ∆H° = +116 kJ/mol (+27.6 kcal/mol) and ∆S° = +117 J-kelvin/mol (+28.0 cal-kelvin/mol). Compute the value of ∆G° for dehydrogenation at room temperature (25°C or 298°K). Is dehydrogenation favored or disfavored?

Circle the most stable alkene in the set of isomers below.

Draw the alkene of formula C₅H₁₀which evolves the most heat per mole upon hydrogenation.

The steroid testosterone has the molecular formula C₁₉H₂₈O₂. Given that there are two π bonds in a molecule of testosterone, how many rings are present in each molecule?

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Draw a mechanism and use a chair structure to explain the major product that is formed in the reaction below.

Provide the proper IUPAC name for the alkene shown below.

Exam 7: Structure and Synthesis of Alkenes; Elimination

Cyclohexane has a molecular formula of C6H12 and an unsaturation number of 1. Is this compound considered to be unsaturated? Why or why not?

Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least heat upon hydrogenation) ?

A newly isolated natural product was found to have the molecular formula C15H28O2. By hydrogenating a sample of the compound, it was determined to possess one π bond. How many rings are present in the compound?

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?

Provide a correct IUPAC name for the structure below.

Provide the proper IUPAC name for the alkene shown below. CH2 CHCH2CH2CH2CH3

Carbon-carbon single bonds tend to be ________ and ________ than carbon-carbon double bonds.

Does the alkene shown below violate Bredt's rule?

Which sequence ranks the following compounds in order of increasing heat of hydrogenation, ΔHhyd? 1 cis-2-butene 2 1-butene 3 cyclohexene

Give the structures of three examples of molecules that have a molecular formula of C6H8. One of the structures should have only one ring and one of the structures should have no rings.

Name the compound shown below.

The carbon-carbon bond length in ethylene is ________ than the carbon-carbon bond length in ethane, and the HCH bond angle in ethylene is ________ the HCH bond angle in ethane.

Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer.

The dehydrogenation of butane to trans-but-2-ene has ∆H° = +116 kJ/mol (+27.6 kcal/mol) and ∆S° = +117 J-kelvin/mol (+28.0 cal-kelvin/mol). Compute the value of ∆G° for dehydrogenation at room temperature (25°C or 298°K). Is dehydrogenation favored or disfavored?

Circle the most stable alkene in the set of isomers below.

Draw the alkene of formula C5H10 which evolves the most heat per mole upon hydrogenation.

The steroid testosterone has the molecular formula C19H28O2. Given that there are two π bonds in a molecule of testosterone, how many rings are present in each molecule?

Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.

Draw a mechanism and use a chair structure to explain the major product that is formed in the reaction below.

Provide the proper IUPAC name for the alkene shown below.

Cyclohexane has a molecular formula of C₆H₁₂ and an unsaturation number of 1. Is this compound considered to be unsaturated? Why or why not?

A newly isolated natural product was found to have the molecular formula C₁₅H₂₈O₂. By hydrogenating a sample of the compound, it was determined to possess one π bond. How many rings are present in the compound?

Provide the proper IUPAC name for the alkene shown below. CH₂ CHCH₂CH₂CH₂CH₃

Carbon-carbon single bonds tend to be and than carbon-carbon double bonds.

Which sequence ranks the following compounds in order of increasing heat of hydrogenation, ΔH_hyd? 1 cis-2-butene 2 1-butene 3 cyclohexene

Give the structures of three examples of molecules that have a molecular formula of C₆H₈. One of the structures should have only one ring and one of the structures should have no rings.

The carbon-carbon bond length in ethylene is than the carbon-carbon bond length in ethane, and the HCH bond angle in ethylene is the HCH bond angle in ethane.

Draw the alkene of formula C₅H₁₀which evolves the most heat per mole upon hydrogenation.

The steroid testosterone has the molecular formula C₁₉H₂₈O₂. Given that there are two π bonds in a molecule of testosterone, how many rings are present in each molecule?