Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

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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.

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Question 1

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

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

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Question 2

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

Provide the structure of isopropyl iodide.

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Question 3

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(CH₃)₂CHI

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

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Question 4

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

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Question 5

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

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Question 6

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

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Question 7

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

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Question 8

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

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Question 9

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.

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Question 10

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

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Question 11

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

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Question 12

Which of the following best describes DDT?

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Question 13

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

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Question 14

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

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Question 15

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?

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Question 16

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

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Question 17

Provide the major organic product of the reaction below.

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Question 18

Provide an acceptable name for the compound shown below.

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Question 19

What is Zaitsev's rule?

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Question 20

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Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

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.

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

Provide the structure of isopropyl iodide.

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

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 ________.

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

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

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

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

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.

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

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

Which of the following best describes DDT?

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

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

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?

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

Provide the major organic product of the reaction below.

Provide an acceptable name for the compound shown below.

What is Zaitsev's rule?

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

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

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

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

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

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

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

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