Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 31, Problem 31.50P
Interpretation Introduction

(a)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: Radical polymerization takes place via free radical intermediate. The peroxide used in this polymerization forms the free radical RO· which acts as the initiator.

The alkenes which have the substituents that can stabilize the radicals undergo radical polymerization.

Expert Solution
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Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  1

Explanation of Solution

The given alkene undergoes radical polymerization in presence of peroxide to form the polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  2

Figure 1

Conclusion

The product for the given reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: The reaction of an olefin with Ziegler-Natta catalyst leads to the formation of a linear and high molecular weight polymer. The components involved in Ziegler-Natta catalyst are TiCl4+Et3Al.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  3

Explanation of Solution

The given alkene undergoes polymerization in presence of Ziegler-Natta to form the linear and high molecular weight polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  4

Figure 2

Conclusion

The product for the given reaction is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: The anionic polymerization is a chain growth polymerization. Anionic polymerization takes place in alkene substituted with electron withdrawing groups and epoxides. In this polymerization the initiator is anion.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  5

Explanation of Solution

The given alkene undergoes anionic polymerization in presence of BuLi to form the polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  6

Figure 3

Conclusion

The product for the given reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: The cationic polymerization is a chain growth polymerization. This polymerization occurs in the alkenes with substituents which can stabilize the intermediate carbocation. This is an electrophilc addition reaction that involves the carbocations as intermediates.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  7

Explanation of Solution

The given alkene undergoes cationic polymerization in presence of boron trifluoride in aqueous medium to form the polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  8

Figure 4

Conclusion

The product for the given reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: The anionic polymerization is a chain growth polymerization. Anionic polymerization takes place in alkene substituted with electron withdrawing groups and epoxides. In this polymerization the initiator is anion.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  9

Explanation of Solution

The given epoxide undergoes anionic polymerization in presence base to form the polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  10

Figure 5

Conclusion

The product for the given reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: In Step-growth polymerization the monomers with different functional groups combine together to form the polymer with the loss of small molecule such as water. For example polyamides, polyesters, polyurethanes, polycarbonates and epoxy resins.

Prepolymer which is composed of polymeric chain with epoxide rings at the each terminal and cross linked polymers. These two components form epoxy resins.

Expert Solution
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Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  11

Explanation of Solution

The resorcinol undergoes step growth polymerization in presence of excess epichlorohydrin to form the polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  12

Figure 6

Conclusion

The product for the given reaction is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: In Step-growth polymerization the monomers with different functional groups combine together to form the polymer with the loss of small molecule such as water. For example polyamides, polyesters, polyurethanes, polycarbonates and epoxy resins.

The polyesters are formed by the reaction of acid and alcohol as monomers.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  13

Explanation of Solution

The given polyester on hydrolysis produces its monomers. The ester linkages are cleaved to produce alcohol and acid. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  14

Figure 7

Conclusion

The product for the given reaction is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: The reaction of monomer unit to produce a chain like or cyclic structure is known as polymerization. In some polymerization, ring formation takes place which are called ring-forming polymerization.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  15

Explanation of Solution

The given compound reacts with base to form the cyclic polymer. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  16

Figure 8

Conclusion

The product for the given reaction is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: In Step-growth polymerization the monomers with different functional groups combine together to form the polymer with the loss of small molecule such as water. For example polyamides, polyesters, polyurethanes, polycarbonates and epoxy resins.

Polyurethanes contain carbonyl compounds bonded to OR and NR2 or NHR group.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  17

Explanation of Solution

The given diisocyanate reacts with the given diol to undergo step growth polymerization in to form the polyurethane. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  18

Figure 9

Conclusion

The product for the given reaction is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The product for the given reaction is to be drawn.

Concept introduction: In Step-growth polymerization the monomers with different functional groups combine together to form the polymer with the loss of small molecule such as water. For example polyamides, polyesters, polyurethanes, polycarbonates and epoxy resins.

Polycarbonates contain carbonyl compounds bonded to two OR groups.

Expert Solution
Check Mark

Answer to Problem 31.50P

The product for the given reaction is,

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  19

Explanation of Solution

The given diol reacts with phosgene to undergo step growth polymerization to form the polycarbonate. The corresponding chemical reaction is shown below.

Organic Chemistry-Package(Custom), Chapter 31, Problem 31.50P , additional homework tip  20

Figure 10

Conclusion

The product for the given reaction is shown in Figure 10.

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Chapter 31 Solutions

Organic Chemistry-Package(Custom)

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
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