Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
Question
Book Icon
Chapter 10, Problem 87P

(a)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 4-Methyl-2-pentene via Hofmann degradation.

Concept introduction:

Generally amines can’t undergo elimination reaction, therefore amines can be converted in to quaternary ammonium halide by treating with ethyl iodide in basic solution of potassium carbonate.

In the reaction, quaternary ammonium halide can be converted in to quaternary ammonium hydroxide by using aqueous silver oxide.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 10, Problem 87P , additional homework tip  1

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 10, Problem 87P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The primary amine starting material should be identified to form a 3-Methyl-l-butene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 10, Problem 87P , additional homework tip  3

(c)

Interpretation Introduction

Interpretation:

The secondary amine starting material should be identified to form a 2-Methyl-1·3-butadiene via Hofmann degradation.

Concept introduction:

Hofmann elimination:

Quaternary ammonium ion undergoes elimination when using strong base like hydroxide ion this reaction is called as Hofmann elimination.

In the reaction, proton abstraction is takes place in β- carbon atom, which is having more number of hydrogen.

Pearson eText Organic Chemistry -- Instant Access (Pearson+), Chapter 10, Problem 87P , additional homework tip  4

Blurred answer
Students have asked these similar questions
3.5 Complete the following sentences to make correct scientific meaning. 3.5.1 The entropy of a perfect gas. 3.5.2 when it expands isothermally. The change in entropy of a substance accompanying a change of state at its transition 3.5.3 temperature is calculated from its of transition. The increase in entropy when a substance is heated is calculated from its
3.4 Consider the internal energy of a substance 3.4.1 Draw a graph showing the variation of internal energy with temperature at constant volume 3.4.2 Write the mathematical expression for the slope in your graph in 3.4.1
For a system, the excited state decays to the ground state with a half-life of 15 ns, emitting radiation of 6000 Å. Determine the Einstein coefficients for stimulated absorption and spontaneous emission and the dipole moment of the transition. Data: epsilon 0 = 8.85419x10-12 C2m-1J-1

Chapter 10 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning