LL ORG CHEM
6th Edition
ISBN: 9781264840083
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 28.2, Problem 4P
Draw the mechanism for the radical
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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?
The 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-)n
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.
Chapter 28 Solutions
LL ORG CHEM
Ch. 28.1 - Prob. 1PCh. 28.2 - Prob. 2PCh. 28.2 - Prob. 3PCh. 28.2 - Draw the mechanism for the radical polymerization...Ch. 28.2 - Prob. 8PCh. 28.2 - Prob. 9PCh. 28.2 - Prob. 10PCh. 28.3 - Problem 30.12
What polymer is formed by anionic...Ch. 28.5 - Prob. 12PCh. 28.5 - Prob. 13P
Ch. 28.6 - Problem 30.15
What polyamide is formed from each...Ch. 28.6 - Prob. 19PCh. 28.7 - Prob. 20PCh. 28.8 - Prob. 21PCh. 28.9 - Prob. 22PCh. 28.9 - Prob. 23PCh. 28 - Prob. 24PCh. 28 - Prob. 25PCh. 28 - 30.30 Draw each polymer in Problem 30.29 using the...Ch. 28 - Prob. 44PCh. 28 - 30.49 Draw the products of each reaction.
a. e....Ch. 28 - Prob. 56PCh. 28 - 30.56 Compound A is a novel poly (ester amide)...Ch. 28 - 30.57 Researchers at Rutgers University have...Ch. 28 - 30.58 Melmac, a thermosetting polymer formed from...Ch. 28 - 30.59 Although chain branching in radical...Ch. 28 - Prob. 61P
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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_forward11. 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_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_forwardQ1: Clarify the differences between the cationic and anionic polymerization in propagation step.arrow_forwardTwo reactions have an error. Circle the reactions that contain mistakes. Explain why. HCI ROOR polymerization t NBS hv Br HBr NMO NaOEt OET ملاarrow_forward
- 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_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_forwardPOLYMER CHEMISTRY Show the mechanism of each item and their products.arrow_forward
- Draw the mechanism for ziegler-natta-catalyzed polymerization of a subdtitude ethylene.arrow_forward2.) Draw out an oligomer of DP=5 for each of these polymers. Disregard stereochemistry (for now). tito n NH₂arrow_forward3. Which of the following could be polymerized by cationic or anionic chain polymerization(or both or neither)? CN Ph он co,CH, Doarrow_forward
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