EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis, is used as an additive in cattle feed. Digoxin is a widely prescribed cardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.
A key step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involved the reaction of compound A and dihalide B with two equivalents of LDA to form C. Draw a stepwise mechanism for this reaction. β-Vetivone contains a spiro ring system—that is, two rings that share a single carbon atom.
Label the alkene in each drug as E or Z. Enclomiphene is one component of the fertility drug Clomid. Tamoxifen is an anticancer drug. Clavulanic acid is sold in combination with the antibiotic amoxicillin under the trade name Augmentin.
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- Compound that is most easily hydrolyzed by acid in water `NH A. В. F C. D.arrow_forwardLabel the alkene in each attached drug as E or Z. Enclomiphene is one component of the fertility drug Clomid. Tamoxifen is an anticancer drug. Clavulanic acid is sold in combination with the antibiotic amoxicillin under the trade name Augmentinarrow_forwardDetermine and draw the structure of compound A. Then, determine the reactant/reagent needed to accomplish the one step transformation from benzene to A. Br₂ FeBr3 H (acid workup) PCC A ?arrow_forward
- Why is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutionsarrow_forwardShown compound is Compound F. Draw THREE (3) possible reactions of carbonyl reduction to form compound F.arrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. Part (b), then CH3COCl, AlCl3arrow_forward
- Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.arrow_forward16.69 Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compaund. You may use benzene, acetylene (HC=CH), ethanol, ethylene oxide, and any inorganic reagents. a. b. CI он C ON d. NO2arrow_forwardBromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 18.34). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.arrow_forward
- Give the structure corresponding to each name (a, b, and c)arrow_forwardWhich of the foll owing lone pairs of purine participate in its aromaticity? A N. N.B N. Carrow_forwardOrganometallic reagents are characterized by a.) polar bonds b.) carbon bonded to an electropositive element c.) carbon behaving as a free carbanion d.) none of thesearrow_forward
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