Question 1

The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. $\textbf{     2011    }$ , 449). The halides in this structure may be classified as ________ and ________.

Accepted Answer

The halides in the structure are located on vicinal carbon atoms (adjacent carbons in the carbon chain) and are also part of an aryl ring system. Therefore, the halides may be classified as both vicinal and aryl. Option A is incorrect because vinyl halides are attached to sp2 hybridized carbon atoms with a double bond to a neighboring carbon, while the halides in the structure are attached to sp3 hybridized carbon atoms. Option C is incorrect because there are no vinyl halides in the structure. Option D is incorrect because geminal halides are attached to the same carbon atom, and the halides in this structure are on adjacent carbon atoms.

Question 2

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why.

Accepted Answer

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Question 3

Arrange the following alkyl halides in order of increasing boiling point: CH₃CH₂Br, CH₃CH₂CH₂Br, (CH₃)₂CHBr, CH₃CH₂F.

Accepted Answer

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Question 4

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Accepted Answer

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Question 5

The term CFC is an abbreviation for ________.

Accepted Answer

The answer of The term CFC is an abbreviation for...

Question 6

When 2,2-dimethylbutane is subjected to free-radical chlorination, ________ distinct monochlorinated products are possible and ________ of these contain asymmetric carbon atoms.

Accepted Answer

2,2-Dimethylbutane can form 4 distinct monochlorinated products because of its structure, which allows for chlorination at different carbon atoms. However, only 2 of these products will have asymmetric carbon atoms, as the chlorination at certain positions introduces chirality.

Question 7

Among the following alkyl halides, choose the one with the lowest boiling point.

Accepted Answer

The boiling point of an alkyl halide increases with increasing carbon chain length and with increasing atomic weight of the halogen. Among the given options, t-butyl chloride has the lowest boiling point because the t-butyl group is highly branched, which decreases the surface area of contact between molecules, hence van der Waals forces are also weaker.

Question 8

Provide the structure of the major organic product in the reaction below.

Accepted Answer

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Question 9

Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Accepted Answer

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Question 10

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the C-F bond. Explain.

Accepted Answer

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Question 11

Provide the major organic product of the reaction below.

Accepted Answer

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Question 12

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Accepted Answer

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Question 13

Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CH₂CN + I^-

Accepted Answer

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Question 14

Which of the following best describes DDT?

Accepted Answer

DDT is a polychlorinated organic compound used as an insecticide. It was widely used in the mid-20th century but has since been banned in many countries due to its harmful effects on the environment and human health.

Question 15

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Accepted Answer

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Question 16

Show how the following reaction might be constructed using an S_N2 reaction by drawing structures for the starting materials.

Accepted Answer

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Question 17

Provide the structure of the major organic product in the reaction below.

Accepted Answer

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Question 18

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

Accepted Answer

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Question 19

What type of intermediate is present in the S_N2 reaction of cyanide with bromoethane?

Accepted Answer

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Question 20

Which of the following alkyl halides has the smallest molecular dipole moment?

Accepted Answer

The molecular dipole moment of an alkyl halide depends on the difference in electronegativity between the carbon and the halogen atom, as well as the bond length and bond angle. Among the given options, the molecule with the smallest dipole moment would be the one with the least electronegative halogen atom. In this case, the halogen in option E (fluorine) is the least electronegative, compared to the others (chlorine, iodine, and bromine) in the other options. Therefore, option E has the smallest molecular dipole moment.

Quiz 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why.

Arrange the following alkyl halides in order of increasing boiling point: CH₃CH₂Br, CH₃CH₂CH₂Br, (CH₃)₂CHBr, CH₃CH₂F.

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

The term CFC is an abbreviation for ________.

When 2,2-dimethylbutane is subjected to free-radical chlorination, distinct monochlorinated products are possible and of these contain asymmetric carbon atoms.

Among the following alkyl halides, choose the one with the lowest boiling point.

Provide the structure of the major organic product in the reaction below.

Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the C-F bond. Explain.

Provide the major organic product of the reaction below.

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CH₂CN + I^-

Which of the following best describes DDT?

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Show how the following reaction might be constructed using an S_N2 reaction by drawing structures for the starting materials.

Provide the structure of the major organic product in the reaction below.

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

What type of intermediate is present in the S_N2 reaction of cyanide with bromoethane?

Which of the following alkyl halides has the smallest molecular dipole moment?

Quiz 6: Alkyl Halides: Nucleophilic Substitution and Elimination

The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. 2011 \textbf{ 2011 } 2011 , 449) . The halides in this structure may be classified as ________ and ________.

Draw the structures of the two major products formed in the following reaction. Indicate which of the two structures would be predicted to predominate under thermodynamic condition and explain why.

Arrange the following alkyl halides in order of increasing boiling point: CH3CH2Br, CH3CH2CH2Br, (CH3)2CHBr, CH3CH2F.

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

The term CFC is an abbreviation for ________.

When 2,2-dimethylbutane is subjected to free-radical chlorination, ________ distinct monochlorinated products are possible and ________ of these contain asymmetric carbon atoms.

Among the following alkyl halides, choose the one with the lowest boiling point.

Provide the structure of the major organic product in the reaction below.

Consider the reaction of (CH3)3CO- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Although F is more electronegative than Cl, the C-Cl bond has a larger dipole moment than the C-F bond. Explain.

Provide the major organic product of the reaction below.

When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase? Explain.

Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CH2CN + I-

Which of the following best describes DDT?

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Show how the following reaction might be constructed using an SN2 reaction by drawing structures for the starting materials.

Provide the structure of the major organic product in the reaction below.

Draw two reasonable resonance structures and the hybrid of the intermediate formed in the following reaction.

What type of intermediate is present in the SN2 reaction of cyanide with bromoethane?

Which of the following alkyl halides has the smallest molecular dipole moment?

Arrange the following alkyl halides in order of increasing boiling point: CH₃CH₂Br, CH₃CH₂CH₂Br, (CH₃)₂CHBr, CH₃CH₂F.

When 2,2-dimethylbutane is subjected to free-radical chlorination, distinct monochlorinated products are possible and of these contain asymmetric carbon atoms.

Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CH₂CN + I^-

Show how the following reaction might be constructed using an S_N2 reaction by drawing structures for the starting materials.

What type of intermediate is present in the S_N2 reaction of cyanide with bromoethane?