Question 1

Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.

Accepted Answer

A)   SN2 and SN1
B)   E1 and E2
C)   SN2 and E2
D)   E1 and SN1
E)   E2 and SN1F) B) and C)
G) D) and E)

Question 2

Provide an acceptable name for the compound shown below.

Accepted Answer

4-bromo-1,...

Question 3

What is Zaitsev's rule?

Accepted Answer

In elimination react...

Question 4

The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?

Accepted Answer

A)   SN1
B)   SN2
C)   E1
D)   E2
E)   E1cbF) B) and E)
G) All of the above

Question 5

In which of the following mechanisms (SN1, SN2, E1, E2)  are alkenes the major reaction products?

Accepted Answer

A)   SN1 only
B)   SN2 only
C)   E1 only
D)   E2 only
E)   both E1 and E2F) A) and D)
G) B) and C)

Question 6

Draw the highest energy transition state in the solvolysis of (CH3)3CI in CH3OH.

Accepted Answer

Question 7

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

Accepted Answer

Question 8

Predict the structure of the expected product for the following reaction.

Accepted Answer

The answer of Predict the structure of the expected product...

Question 9

Arrange the following substrates in order of their increasing SN2 reactivity with NaCN:
bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Accepted Answer

2-bromo-2-methylpentane < 1-chloro-2,2-dimethylpentane < 1-chloro-3,3-dimethylpentane < bromoethane

Question 10

Which of the following alkyl chlorides will undergo SN2 reaction most readily?

Accepted Answer

A)   1-chloro-4-methylpentane
B)   2-chloro-4-methylpentane
C)   2-chloro-3-methylpentane
D)   3-chloro-2-methylpentane
E)   2-chloro-2-methylpentaneF) All of the above
G) A) and D)

Question 11

Which is more nucleophilic, t-butoxide or ethoxide? Explain.

Accepted Answer

Ethoxide is the better nucleophile. The steric bulk of t-butoxide decreases its effectiveness as a nucleophile.

Question 12

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

Accepted Answer

A)   vicinal & vinyl
B)   vicinal & aryl
C)   vinyl & aryl
D)   vinyl & geminal E) B) and D)
F) C) and D)

Question 13

Which of the following best describes DDT?

Accepted Answer

A)   a chlorocarbon used to decaffeinate coffee beans
B)   a polybrominated organic compound used as a herbicide
C)   a Freon used as a foaming agent
D)   a mixed alkyl halide used as an anesthetic
E)   a polychlorinated organic compound used as an insecticideF) C) and E)
G) B) and C)

Question 14

Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Accepted Answer

The cis isomer reacts more quickly. An a...

Question 15

Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting) . N1 solvolysis with methanol and heat (slowest to fastest reacting) .   A)  3

Accepted Answer

A)   3 
B)   2 
C)   5 
D)   2 
E)   1 < 2 < 5 < 4 < 3F) C) and E)
G) All of the above

Question 16

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

Accepted Answer

A)   cyclohexyl bromide
B)   methyl iodide
C)   isopropyl chloride
D)   3-chloropentane
E)   3-iodo-3-methylpentaneF) D) and E)
G) B) and C)

Question 17

Provide the major organic product of the reaction below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 18

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

Accepted Answer

A)   4, 2
B)   5, 0
C)   3, 0
D)   5, 2
E)   4, 0F) C) and D)
G) None of the above

Question 19

Provide the structure of isopropyl iodide.

Accepted Answer

(CH₃)₂CHI

Question 20

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Accepted Answer

No. All primary iodides are no...

Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.

Correct Answer
verified

Provide an acceptable name for the compound shown below.

Correct Answer
verified
4-bromo-1,...
View Answer

What is Zaitsev's rule?

Correct Answer
verified
In elimination react...
View Answer

The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?

Correct Answer
verified

In which of the following mechanisms (S_N1, S_N2, E1, E2) are alkenes the major reaction products?

Correct Answer
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Draw the highest energy transition state in the solvolysis of (CH₃)₃CI in CH₃OH.

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

Correct Answer
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Predict the structure of the expected product for the following reaction.

Correct Answer
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Arrange the following substrates in order of their increasing SN2 reactivity with NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Correct Answer
verified
2-bromo-2-methylpentane < 1-chloro-2,2-dimethylpentane < 1-chloro-3,3-dimethylpentane < bromoethane

Which of the following alkyl chlorides will undergo S_N2 reaction most readily?

Correct Answer
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Which is more nucleophilic, t-butoxide or ethoxide? Explain.

Correct Answer
verified
Ethoxide is the better nucleophile. The steric bulk of t-butoxide decreases its effectiveness as a nucleophile.

Correct Answer
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Which of the following best describes DDT?

Correct Answer
verified

Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Correct Answer
verified
The cis isomer reacts more quickly. An a...
View Answer

Rank the following molecules in order of increasing relative rate of S_N1 solvolysis with methanol and heat (slowest to fastest reacting) .

Correct Answer
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Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

Correct Answer
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Provide the major organic product of the reaction below.

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

Correct Answer
verified

Provide the structure of isopropyl iodide.

Correct Answer
verified
(CH₃)₂CHI

Do all primary alkyl iodides undergo S_N2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Correct Answer
verified
No. All primary iodides are no...
View Answer

Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.

Correct AnswerverifiedShow Answer

Provide an acceptable name for the compound shown below.

Correct Answerverified4-bromo-1,...View AnswerShow Answer

What is Zaitsev's rule?

Correct AnswerverifiedIn elimination react...View AnswerShow Answer

The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?

Correct AnswerverifiedShow Answer

In which of the following mechanisms (SN1, SN2, E1, E2) are alkenes the major reaction products?

Correct AnswerverifiedShow Answer

Draw the highest energy transition state in the solvolysis of (CH3)3CI in CH3OH.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Predict the structure of the expected product for the following reaction.

Correct AnswerverifiedShow Answer

Arrange the following substrates in order of their increasing SN2 reactivity with NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

Correct Answerverified2-bromo-2-methylpentane < 1-chloro-2,2-dimethylpentane < 1-chloro-3,3-dimethylpentane < bromoethane

Which of the following alkyl chlorides will undergo SN2 reaction most readily?

Correct AnswerverifiedShow Answer

Which is more nucleophilic, t-butoxide or ethoxide? Explain.

Correct AnswerverifiedEthoxide is the better nucleophile. The steric bulk of t-butoxide decreases its effectiveness as a nucleophile.

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 ________.

Correct AnswerverifiedShow Answer

Which of the following best describes DDT?

Correct AnswerverifiedShow Answer

Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

Correct AnswerverifiedThe cis isomer reacts more quickly. An a...View AnswerShow Answer

Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting) .

Correct AnswerverifiedShow Answer

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

Correct AnswerverifiedShow Answer

Provide the major organic product of the reaction below.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Provide the structure of isopropyl iodide.

Correct Answerverified(CH3)2CHI

Do all primary alkyl iodides undergo SN2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Correct AnswerverifiedNo. All primary iodides are no...View AnswerShow Answer

Correct Answer
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Correct Answer
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4-bromo-1,...
View Answer

Correct Answer
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In elimination react...
View Answer

Correct Answer
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In which of the following mechanisms (S_N1, S_N2, E1, E2) are alkenes the major reaction products?

Correct Answer
verified

Draw the highest energy transition state in the solvolysis of (CH₃)₃CI in CH₃OH.

Correct Answer
verified

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

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified
2-bromo-2-methylpentane < 1-chloro-2,2-dimethylpentane < 1-chloro-3,3-dimethylpentane < bromoethane

Which of the following alkyl chlorides will undergo S_N2 reaction most readily?

Correct Answer
verified

Correct Answer
verified
Ethoxide is the better nucleophile. The steric bulk of t-butoxide decreases its effectiveness as a nucleophile.

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified
The cis isomer reacts more quickly. An a...
View Answer

Rank the following molecules in order of increasing relative rate of S_N1 solvolysis with methanol and heat (slowest to fastest reacting) .

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

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

Correct Answer
verified

Correct Answer
verified
(CH₃)₂CHI

Do all primary alkyl iodides undergo S_N2 reactions with sodium cyanide in DMSO at identical rates? Explain.

Correct Answer
verified
No. All primary iodides are no...
View Answer