Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
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Chapter 30, Problem 30.4P
Draw the mechanism for the radical
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When 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.
(a) Explain why poly(vinyl alcohol) cannot be prepared by the radical polymerization of vinyl alcohol (CH2=CHOH). (b) Devise a stepwise synthesis of poly(vinyl alcohol) from vinyl acetate (CH2=CHOCOCH3). (c) How can poly(vinyl alcohol) be converted to poly(vinyl butyral), a polymer used in windshield safety glass?
Chapter 30 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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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- 2) (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_forwardReaction (blank) Choose your answer here in the radical polymerization of styrene would afford the more stable radical intermediate. A) 1 B) 2 C) 1 or 2arrow_forward1. Give the detailed arrow-pushing mechanism for the free radical polymerization of methyl methacrylate. Show the initiation step and the addition of at least 2 monomers. You do not need to show a termination step, but do show the [ Ja notation of the final polymer. NEATNESS COUNTS! **Attacn yuui TANarrow_forward
- Draw the organic product of the following reaction. CH3 m-CICgH,CO;H • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, just draw one stereoisomer. • If more than one product is possible, only draw the major product. opy astearrow_forward08.20b 1) ВН, THF 2) H,O2, NaOH Modify the given carbon skeleton to draw the major product(s) of the given reaction. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. CHarrow_forwardWhat about anionic polymerization? - same answer choicesarrow_forward
- HC CH CH3CO2H H,SO, H3C-C-O-C=CH2 H HgSO, Acetylene Acetic Acid Vinyl acetate Acetylene reacts with acetic acid in the presence of H,SO4 and HgSO4 to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps: 1. Formation of a bridged mercurinium ion intermediate between Hg- and acetylene; 2. Addition of acetic acid to open the three-membered ring; 3. Proton transfer to solvent to give an organomercury vinyl ester3; 4. Addition of H to the alkene to form a carbocation; 2+ 5. Expulsion of Hg²+ to form the alkene. Diagram the mechanism on a separate sheet of paper, and then draw the structure of the product(s) of step 3. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Draw organic species only. • Do not include counter-ions, e.g., Na, I, in your answer.arrow_forwardDraw the organic products formed in attached reactionarrow_forward(а) Н (Б) Н (c) H Each of the monomers shown here can undergo free radical polymerization. For each polymerization: (i) Show the mechanism for the first two propagation steps, using benzoyl peroxide as the initiator. (ii) Draw the condensed formula for the polymer, showing the repeating unit. (iii) Provide a name for the polymer. H H H CI Hi c=0 H OCH3 H,N Vinylidene chloride Acrylamide Methyl vinyl etherarrow_forward
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