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The active ingredient of the insect repellent Off is N, N-diethyl-m-toluamide,
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Organic Chemistry
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- 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
- 2-Propylpentanoic acid (valproic acid) is an effective drug for treatment of several types of epilepsy, particularly absence seizures, which are generalized epileptic seizures characterized by brief and abrupt loss of consciousness. Propose a synthesis of valproic acid starting with diethyl malonate.arrow_forwardProvide reagentsarrow_forwardQII: Starting from toluene as the only organic reagent you have and use any other inorganic reagents to prepare:arrow_forward
- 22). What is the major product of the following reactions? (A) (B) Br 1) NaCN 2) CH3MgBr 3) H30*/H₂O (C) LOH (D) CNarrow_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_forwardH₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br заarrow_forward
- b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: РОС3, NazCOз, H20 E F (ii) Account for the regioselectivity observed.arrow_forward17arrow_forwardH3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_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