ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 30, Problem 30.4P
Draw the mechanism for the radical
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Draw the mechanism for the radical polymerization of vinyl acetate (CH2 = CHOCOCH3) using
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Propylene does not undergo free radical polymerization readily because there are two competing steps after initiation: propagation and hydrogen atom abstraction.(a) Using a generic radical R• as a reactant with propylene, draw the mechanism and products for the two competing steps.(b) Which step produces the more stable product?(c) How do your results explain propylene’s poor reactivity in free radical polymerization?
Two reactions have an error. Circle the reactions that contain mistakes. Explain why.
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Chapter 30 Solutions
ORGANIC CHEMISTRY
Ch. 30 - Prob. 30.1PCh. 30 - Prob. 30.2PCh. 30 - Prob. 30.3PCh. 30 - Draw the mechanism for the radical polymerization...Ch. 30 - Prob. 30.5PCh. 30 - Prob. 30.6PCh. 30 - Prob. 30.7PCh. 30 - Prob. 30.8PCh. 30 - Prob. 30.9PCh. 30 - Prob. 30.10P
Ch. 30 - Prob. 30.11PCh. 30 - Problem 30.12
What polymer is formed by anionic...Ch. 30 - Prob. 30.13PCh. 30 - Prob. 30.14PCh. 30 - Problem 30.15
What polyamide is formed from each...Ch. 30 - Prob. 30.16PCh. 30 - Prob. 30.17PCh. 30 - Prob. 30.18PCh. 30 - Prob. 30.19PCh. 30 - Prob. 30.20PCh. 30 - Prob. 30.21PCh. 30 - Prob. 30.22PCh. 30 - Prob. 30.23PCh. 30 - Prob. 30.24PCh. 30 - Prob. 30.25PCh. 30 - 30.26 Draw the structure of the polymer formed by...Ch. 30 - Prob. 30.27PCh. 30 - Prob. 30.28PCh. 30 - Prob. 30.29PCh. 30 - 30.30 Draw each polymer in Problem 30.29 using the...Ch. 30 - Prob. 30.31PCh. 30 - Prob. 30.32PCh. 30 - Prob. 30.33PCh. 30 - Prob. 30.34PCh. 30 - Prob. 30.35PCh. 30 - Prob. 30.36PCh. 30 - Prob. 30.37PCh. 30 - Prob. 30.38PCh. 30 - 30.39 Draw a stepwise mechanism for the...Ch. 30 - 30.40 Cationic polymerization of 3-phenylpropene ...Ch. 30 - Prob. 30.41PCh. 30 - Prob. 30.42PCh. 30 - 30.43 Although styrene undergoes both cationic and...Ch. 30 - 30.44 Rank the following compounds in order of...Ch. 30 - Prob. 30.45PCh. 30 - Prob. 30.46PCh. 30 - 30.47 Draw a stepwise mechanism for the following...Ch. 30 - 30.48 Draw a stepwise mechanism for the reaction...Ch. 30 - 30.49 Draw the products of each reaction.
a. e....Ch. 30 - Prob. 30.50PCh. 30 - Prob. 30.51PCh. 30 - 30.52 (a) Explain why poly (vinyl alcohol) cannot...Ch. 30 - 30.53 Devise a synthesis of terephthalic acid and...Ch. 30 - Prob. 30.54PCh. 30 - Prob. 30.55PCh. 30 - 30.56 Compound A is a novel poly (ester amide)...Ch. 30 - 30.57 Researchers at Rutgers University have...Ch. 30 - 30.58 Melmac, a thermosetting polymer formed from...Ch. 30 - 30.59 Although chain branching in radical...Ch. 30 - Prob. 30.60P
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- Styrene derivatives such as A can be polymerized by way of cationic rather than radical intermediates. Cationic polymerization is an example of electrophilic addition to an alkene involving carbocations. a.) Draw a short segment of the polymer formed by the polymerization ofA.b.) Why does A react faster than styrene (C6H5CH=CH2) in a cationicpolymerization?arrow_forwardWhen HBr adds to (CH3)2C = CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.arrow_forwardThe product of the polymerization of CH3 CH3 T bv) (-CH₂-CH-CH₂-CH-)n. ds) (-CH₂-CH = CH-CH₂-CH = CH-)n CH₂=CH-CH3 is: CH3 CH3 no) ( — CH= C -CH=C-) bc) (-CH=CH-CH₂-CH=CH-CH₂-)narrow_forward
- 11. Draw the repeating segment for the polymer formed from the reactions using the given monomer(s). (a) H₂C=CH₂ (b) CICH₂CH₂OCH₂CH₂CI+ (c) O=C=N- TICI4 (CH3CH₂)2AICI (d) HO- CH3 CH3 N. H -N=C=O + HOCH₂CH₂OH OH + & aminearrow_forwardLactams (cyclic amides) can undergo anionic ring-opening polymerization when treated with a small amount of a strong base such as NaH, as shown here. Draw the mechanism for the initiation and first two propagationsteps for this polymerization, and draw the repeating unit of the resulting polymer.arrow_forwardQ1: Clarify the differences between the cationic and anionic polymerization in propagation step.arrow_forward
- i)State the type of reaction. (ii) What is the function of the sunlight in the reaction? (iii) Draw the structure of monosubstituted products, A and B. Label the major product. (iv) Draw the propagation steps in the mechanism for the formation of the major product.arrow_forward2) (4pts) Classify each reaction as addition, elimination, substitution, or rearrangement. A) CH;CH2B LIOH CH;CH2OH LiBr B) CH;CH2CH,Cl CH-CH-CH2 + + HCl C) CH;CH=CH2 H2 CH;CH2CH3 Verdana 10pt B IU A varrow_forwardA ketene acetal can undergo free radical ring-opening polymerization, as shown below. After the initial radical, R•, is produced, the catalytic cycle that adds each monomer to the growing chain consists of two steps. Draw the mechanism for those two steps and draw the repeating unit for the resulting polymer.arrow_forward
- POLYMER CHEMISTRY Show the mechanism of each item and their products.arrow_forward3. Which of the following could be polymerized by cationic or anionic chain polymerization(or both or neither)? CN Ph он co,CH, Doarrow_forwardDraw the mechanism for ziegler-natta-catalyzed polymerization of a subdtitude ethylene.arrow_forward
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