Concept explainers
The active ingredient of the insect repellent Off is N, N-diethyl-m-toluamide,
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Chemistry: The Central Science (14th Edition)
College Physics: A Strategic Approach (3rd Edition)
Chemistry: Structure and Properties (2nd Edition)
Applications and Investigations in Earth Science (9th Edition)
Campbell Biology (11th Edition)
Cosmic Perspective Fundamentals
- N,N-Diethyl-m-toluamide (DEET) is the active ingredient in many insect-repellent preparations. How might you synthesize this substance from m-bromotoluene?arrow_forward3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and gives compound A. Propose a structural formula for compound A. R&N NH, + Br. C15H93NO, + 2 R,NH Br OCH Br 1-Aminoadamantane Methyl 2,4-dibromobutanoate Aarrow_forwardQ5:- Give structures and names of the principal organic reactants and products of the following reactions. a- pentinoic acid from butanol b- Preparation of acid anhydrides Q6:- Rank the following substances in order of increasing acidity , Justify your choice. benzoic acid, p-chlorobenzoic acid , 2,4-dichlorobenzoic acid , 2,4,6-trichlorobenzoic acidarrow_forward
- PQ-20. This type of reaction, typical of carboxylic acids, esters, acid halides, anhydrides and amines, is called: (A) a bimolecular nucleophilic substitution. (C) an electrophilic substitution. (A) (A) H3C-C-OCH₂CH3 OH R CI PQ-21 What would be hydrolyzed most slowly with aqueous NaOH? lo (B) OH₂ (C) H3C-C-OCH₂CH3 H3C-C- H CI + H₂O (B) a nucleophilic addition. (D) a nucleophilic acyl substitution. (C) PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? RiOH OH (D) H3C- (D) OH (B) H3C-C-OCH₂CH3 OH₂ + HCI si inarrow_forwardQII: Starting from toluene as the only organic reagent you have and use any other inorganic reagents to prepare:arrow_forwardSeveral sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.arrow_forward
- As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardDihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.arrow_forward
- Draw a resonance structure of the acetonitrile anion, -: CH2CN, and account for the acidity of nitriles.arrow_forwardGive Reaction of +NO with 1° Amines ?arrow_forwardBrasilenyne is isolated from the digestive gland of the sea hare; it shows significant antifeedant activity. Choose the best reagents to complete the final reaction in the synthesis of brasilenyne. HO U Q A B C SOCI2 pyridine PBr3 DMF NaCl DMF Cl2arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning