Organic Chemistry - With Access (Custom)
4th Edition
ISBN: 9781259147760
Author: OHIO UNIV.
Publisher: MCG
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Chapter 9, Problem 9.83P
Aziridines are heterocycles that contain an N atom in a three-membered ring. Like
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Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.
An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.
Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.
Chapter 9 Solutions
Organic Chemistry - With Access (Custom)
Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2PCh. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5PCh. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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- The shrub ma huang (Section 5.4A) contains two biologically activestereoisomers—ephedrine and pseudoephedrine—with two stereogeniccenters as shown in the given structure. Ephedrine is one component ofa once-popular combination drug used by body builders to increaseenergy and alertness, whereas pseudoephedrine is a nasaldecongestant.a.) Draw the structure of naturally occurring (−)-ephedrine, which has the1R,2S configuration.b.) Draw the structure of naturally occurring (+)-pseudoephedrine, whichhas the 1S,2S configuration.c.) How are ephedrine and pseudoephedrine related?d.) Draw all other stereoisomers of (−)-ephedrine and (+) pseudoephedrine, and give the R,S designation for all stereogeniccenters.e.) How is each compound drawn in part (d) related to (−)-ephedrine?arrow_forwardNicotinic acid, more commonly named niacin, is one of the B vitamins. Show how nicotinic acid can be converted to (a) ethyl nicotinate and then to (b) nicotinamide.arrow_forwardIbufenac, a para-disubstituted arene with the structureHO2CCH2C6H4CH2CH(CH3)2 , is a much more potent analgesic thanaspirin, but it was never sold commercially because it caused livertoxicity in some clinical trials. Devise a synthesis of ibufenac frombenzene and organic halides having fewer than five carbons.arrow_forward
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- Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?arrow_forwardRank the labeled N atoms in the anticancer drug imatinib (trade name Gleevec) in order of increasing basicity. Imatinib, sold as a salt with methanesulfonic acid (CH3SO3H), is used for the treatment of chronic myeloid leukemia as well as certain gastrointestinal tumors.arrow_forwardIdentify compounds A, B, and C. a.) Compound A has molecular formula C8H12 and reacts with two equivalents of H2. A gives HCOCH2CH2CHO as the only product ofoxidative cleavage with O3 followed by CH3SCH3. b.) Compound B has molecular formula C6H10 and gives(CH3)2CHCH2CH2CH3 when treated with excess H2 in the presence ofPd. B reacts with NaNH2 and CH3I to form compound C (molecularformula C7H12).arrow_forward
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