ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 30, Problem 30.40P
Cationic
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Draw the organic products formed when cyclopentene is treated withfollowing reagent.
[1] CH3CO3H; [2] H2O, HO−
Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.
The reaction of p-cresol with CH2=O resembles the reaction of phenol (PhOH) with CH2=O, except that the resulting polymer is thermoplastic but not thermosetting. Draw the structure of the polymer formed, and explain why the properties of these two polymers are so different.
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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- (a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.arrow_forwardThe reaction of p-cresol with CH2=O resembles the reaction of phenol (PhOH) with CH2=O, except that the resulting polymer is thermoplastic but not thermosetting. Draw the structure of the polymer formed, and explain why the properties of these two polymers are so different.arrow_forwardLess stable alkenes can be isomerized to more stable alkenes by treatment with strong acid. For example, 2,3- dimethylbut-1-ene is converted to 2,3-dimethylbut-2-ene when treated with H2SO4. Draw a stepwise mechanism for this isomerization process.arrow_forward
- Draw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.arrow_forward(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?arrow_forwardDevise a synthesis of OHC(CH2)4CHO from cyclohexane using any required organic or inorganic reagents.arrow_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_forward(a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forwardDraw a stepwise mechanism for the following substitution. Explain why 2-chloropyridine reacts faster than chlorobenzene in this type of reaction.arrow_forward
- a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forward6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOHarrow_forwardFor alkenes A, B, C, and D: (a) Rank A—D in order of increasing heat ofhydrogenation; (b) rank A—D in order of increasing rate of reaction withH2, Pd-C; (c) draw the products formed when each alkene is treated withozone, followed by Zn, H2O.arrow_forward
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