Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 31, Problem 31.44P

Although styrene undergoes both cationic and anionic polymerization equally well, one method is often preferred with substituted styrenes. Which method is preferred with each compound? Explain.

a. Chapter 31, Problem 31.44P, 30.43 Although styrene undergoes both cationic and anionic polymerization equally well, one method , example  1 c. Chapter 31, Problem 31.44P, 30.43 Although styrene undergoes both cationic and anionic polymerization equally well, one method , example  2

b. Chapter 31, Problem 31.44P, 30.43 Although styrene undergoes both cationic and anionic polymerization equally well, one method , example  3 d. Chapter 31, Problem 31.44P, 30.43 Although styrene undergoes both cationic and anionic polymerization equally well, one method , example  4

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The method, anionic or cationic polymerization preferred with the given substituted styrene is to be identified, and an explanation corresponding to it is to be stated.

Concept introduction: An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

Answer to Problem 31.44P

The given substituted styrene prefers to undergo cationic polymerization, due to presence of electron releasing group on benzene ring.

Explanation of Solution

The given substituted styrene resembles to CH2=CHZ alkene, where Z=C6H4OCH3. This means benzene ring is substituted with methoxy group. The methoxy group is an electron releasing group.

An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

An electron releasing group releases electron density towards benzene ring and stabilizes carbocation formed during the cationic polymerization, whereas an electron withdrawing group withdraws electron density towards itself and stabilizes carbanion formed during the anionic polymerization.

Since the given substituted styrene involves bonding of an electron releasing group to benzene ring, it prefers to undergo cationic polymerization.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:The method, anionic or cationic polymerization preferred with the given substituted styrene is to be identified, and an explanation corresponding to it is to be stated.

Concept introduction: An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

Answer to Problem 31.44P

The given substituted styrene prefers to undergo anionic polymerization, due to presence of electron withdrawing group on benzene ring.

Explanation of Solution

The given substituted styrene resembles to CH2=CHZ alkene, where Z=C6H4OCH3. This means benzene ring is substituted with nitro group. The nitro group is an electron withdrawing group.

An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

An electron releasing group releases electron density towards benzene ring and stabilizes carbocation formed during the cationic polymerization, whereas an electron withdrawing group withdraws electron density towards itself and stabilizes carbanion formed during the anionic polymerization.

Since the given substituted styrene involves bonding of an electron withdrawing group to benzene ring, it prefers to undergo anionic polymerization.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation:The method, anionic or cationic polymerization preferred with the given substituted styrene is to be identified, and an explanation corresponding to it is to be stated.

Concept introduction: An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

Answer to Problem 31.44P

The given substituted styrene prefers to undergo anionic polymerization, due to presence of electron withdrawing group on benzene ring.

Explanation of Solution

The given substituted styrene resembles to CH2=CHZ alkene, where Z=C6H4OCH3. This means benzene ring is substituted with CF3 group. The CF3 group is an electron withdrawing group.

An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

An electron releasing group releases electron density towards benzene ring and stabilizes carbocation formed during the cationic polymerization, whereas an electron withdrawing group withdraws electron density towards itself and stabilizes carbanion formed during the anionic polymerization.

Since the given substituted styrene involves bonding of an electron withdrawing group to benzene ring, it prefers to undergo anionic polymerization.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation:The method, anionic or cationic polymerization preferred with the given substituted styrene is to be identified, and an explanation corresponding to it is to be stated.

Concept introduction: An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

Answer to Problem 31.44P

The given substituted styrene prefers to undergo cationic polymerization, due to presence of electron releasing group on benzene ring.

Explanation of Solution

The given substituted styrene resembles to CH2=CHZ alkene, where Z=C6H4OCH3. This means benzene ring is substituted with ethyl group. The ethyl group is an electron releasing group.

An alkene (CH2=CHZ) that contains electron withdrawing group as Z group prefers to undergo anionic polymerization to yield addition polymers. On the other hand, an alkene (CH2=CHZ) that contains electron releasing group as Z group prefers to undergo cationic polymerization to yield addition polymers.

An electron releasing group releases electron density towards benzene ring and stabilizes carbocation formed during the cationic polymerization, whereas an electron withdrawing group withdraws electron density towards itself and stabilizes carbanion formed during the anionic polymerization.

Since the given substituted styrene involves bonding of an electron releasing group to benzene ring, it prefers to undergo cationic polymerization.

Conclusion

(a) The given substituted styrene prefers to undergo cationic polymerization, due to presence of an electron releasing group on benzene ring.

(b) The given substituted styrene prefers to undergo anionic polymerization, due to presence of an electron withdrawing group on benzene ring.

(c) The given substituted styrene prefers to undergo anionic polymerization, due to presence of an electron withdrawing group on benzene ring.

(d) The given substituted styrene prefers to undergo cationic polymerization, due to presence of an electron releasing group on benzene ring.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Briefly describe the compounds called carboranes.
Please don't use Ai solution
None

Chapter 31 Solutions

Organic Chemistry

Ch. 31 - Prob. 31.11PCh. 31 - Problem 30.12 What polymer is formed by anionic...Ch. 31 - Prob. 31.13PCh. 31 - Prob. 31.14PCh. 31 - Problem 30.15 What polyamide is formed from each...Ch. 31 - Prob. 31.16PCh. 31 - Prob. 31.17PCh. 31 - Prob. 31.18PCh. 31 - Prob. 31.19PCh. 31 - Prob. 31.20PCh. 31 - Prob. 31.21PCh. 31 - Prob. 31.22PCh. 31 - Prob. 31.23PCh. 31 - Prob. 31.24PCh. 31 - Prob. 31.25PCh. 31 - Prob. 31.26PCh. 31 - 30.26 Draw the structure of the polymer formed by...Ch. 31 - Prob. 31.28PCh. 31 - Prob. 31.29PCh. 31 - Prob. 31.30PCh. 31 - Prob. 31.31PCh. 31 - Prob. 31.32PCh. 31 - Prob. 31.33PCh. 31 - Prob. 31.34PCh. 31 - Prob. 31.35PCh. 31 - Prob. 31.36PCh. 31 - Prob. 31.37PCh. 31 - Prob. 31.38PCh. 31 - Prob. 31.39PCh. 31 - 30.39 Draw a stepwise mechanism for the...Ch. 31 - 30.40 Cationic polymerization of 3-phenylpropene ...Ch. 31 - Prob. 31.42PCh. 31 - Prob. 31.43PCh. 31 - 30.43 Although styrene undergoes both cationic and...Ch. 31 - 30.44 Rank the following compounds in order of...Ch. 31 - Prob. 31.46PCh. 31 - Prob. 31.47PCh. 31 - 30.47 Draw a stepwise mechanism for the following...Ch. 31 - 30.48 Draw a stepwise mechanism for the reaction...Ch. 31 - Prob. 31.50PCh. 31 - Prob. 31.51PCh. 31 - Prob. 31.52PCh. 31 - 30.52 (a) Explain why poly (vinyl alcohol) cannot...Ch. 31 - Prob. 31.54PCh. 31 - 30.53 Devise a synthesis of terephthalic acid and...Ch. 31 - Prob. 31.56PCh. 31 - Prob. 31.57PCh. 31 - 30.56 Compound A is a novel poly (ester amide)...Ch. 31 - Researchers at Rutgers University have developed...Ch. 31 - 30.58 Melmac, a thermosetting polymer formed from...Ch. 31 - 30.59 Although chain branching in radical...Ch. 31 - Prob. 31.62P
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
Text book image
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Text book image
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
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
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
CBSE Class 12 Chemistry || Polymers || Full Chapter || By Shiksha House; Author: Best for NEET;https://www.youtube.com/watch?v=OxdJlS0xZ0Y;License: Standard YouTube License, CC-BY