Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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Chapter 25, Problem 25.62P
Interpretation Introduction

(a)

Interpretation: The products formed by the reaction of given compound with excess CH3I followed by Ag2O and heat are to be drawn.

Concept introduction: Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

Expert Solution
Check Mark

Answer to Problem 25.62P

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below:

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  1

Explanation of Solution

Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below.

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  2

Figure 1

Conclusion

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the reaction of given compound with excess CH3I followed by Ag2O and heat are to be drawn.

Concept introduction: Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

Expert Solution
Check Mark

Answer to Problem 25.62P

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below:

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  3

Explanation of Solution

Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below.

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  4

Figure 2

Conclusion

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the reaction of given compound with excess CH3I followed by Ag2O and heat are to be drawn.

Concept introduction: Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

Expert Solution
Check Mark

Answer to Problem 25.62P

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below:

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  5

Explanation of Solution

Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below.

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  6

Figure 3

Conclusion

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the reaction of given compound with excess CH3I followed by Ag2O and heat are to be drawn.

Concept introduction: Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

Expert Solution
Check Mark

Answer to Problem 25.62P

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below:

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  7

Explanation of Solution

Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below.

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  8

Figure 4

Conclusion

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products formed by the reaction of given compound with excess CH3I followed by Ag2O and heat are to be drawn.

Concept introduction: Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

Expert Solution
Check Mark

Answer to Problem 25.62P

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below:

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  9

Explanation of Solution

Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product formed by the Hofmann elimination of amines is alkene. The removal of proton from β carbon atom of ammonium salt leads to the formation of π bond of the alkene. The mechanism followed in the Hofmann elimination is E2.

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown below.

Organic Chemistry, Chapter 25, Problem 25.62P , additional homework tip  10

Figure 5

Conclusion

The products formed by the reaction of given compound with excess CH3I followed by Ag2O are shown in Figure 5.

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Chapter 25 Solutions

Organic Chemistry

Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Draw the products of each acidbase reaction....Ch. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Problem 25.22 Which nitrogen atom in each compound...Ch. 25 - Which N atom in each drug is more basic? a. b. c.Ch. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.28 Draw the major product formed in...Ch. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Problem 25.31 Devise a synthesis of each compound...Ch. 25 - Prob. 25.35PCh. 25 - Problem 25.33 What starting materials are needed...Ch. 25 - Problem 25.34 (a) What two components are needed...Ch. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Prob. 25.44PCh. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Decide which N atom in each molecule is most basic...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - How would you prepare 3-phenyl-1-propanamine...Ch. 25 - Prob. 25.55PCh. 25 - Prob. 25.56PCh. 25 - Prob. 25.57PCh. 25 - Prob. 25.58PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.61PCh. 25 - Prob. 25.62PCh. 25 - Prob. 25.63PCh. 25 - Prob. 25.64PCh. 25 - Prob. 25.65PCh. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.72PCh. 25 - Tertiary (3) aromatic amines react with NaNO2 and...Ch. 25 - Prob. 25.74PCh. 25 - Devise a synthesis of each compound from benzene....Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78PCh. 25 - Prob. 25.79PCh. 25 - Synthesize each compound from benzene. Use a...Ch. 25 - Prob. 25.81PCh. 25 - Devise a synthesis of each compound from benzene,...Ch. 25 - Prob. 25.83PCh. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.86PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.88PCh. 25 - Prob. 25.89PCh. 25 - Prob. 25.90P
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