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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardFollowing is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardDihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid, ArSO3H. Propose a mechanism for this conversion.arrow_forward
- Treatment 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_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardThe first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R—CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.arrow_forward
- Propose a mechanism for this reaction. Account for both its regioselectivity and stereoselectivity.arrow_forwardThe following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine (NH2OH). Propose a mechanism to account for the inhibition and for the reactivation.arrow_forwardDraw the products of the diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + Δarrow_forward
- A(n) A(n) H₂N- H | O || H₂N -CICIO _ HO ||| H Glycine OH OH OH T CH₂-C-CH₂ H Glycerol H O H H CH₂ Glycylalanine C-N-C + H₂N- C-O HO T || CICIO CH₂ Alanine reaction converts glycylalanine to glycine and alanine. This reaction requires OH O OH I I CH₂-C-CH₂ Dihydroxyacetone reaction converts glycerol to dihydroxyacetone. This reaction requires and also producesarrow_forwardWhat is the right answer?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
- 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