The following bicyclic ketone has two a-carbons and three a-hydrogens. When this moleculeis treated with D,O in the presence of an acid catalyst, only two of the three a-hydrogensexchange with deuterium. The a-hydrogen at the bridgehead does not exchange.Hthese two a-hydrogens exchangeH.this a-hydrogendoes not exchangeHHow do you account for the fact that two a-hydrogens do exchange but the thirddoes not? You will find it helpful to build models of the enols by which exchange ofa-hydrogens occurs.

Exchange of alpha-hydrogen occurs through keto-enol tautomerism and an enol intermediate. The key to…

Answered: The following bicyclic ketone has two…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Prostaglandins are a class of cicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax = Km mM/min mM
Choose the reagent(s) from the list at right and give the number of equivalents required. Draw out the R group of the reagent needed. Draw the by-products of the reaction. 26. 27. H C-C Bond Forming Reagents: 1) R-MgBr 2) H3O*CH 1) R-Li 2) H₂O*CI 1) R-CH₂X, PPh3, 2) n-BuLi 1) (EtO)2P(=O)CH₂EWG, 2) NaH CO₂Et
Draw the structure(s) of the major organic product(s) of the following reaction. aqueous H₂SO + KCN
Draw out a complete arrow-pushing mechanism for the following reaction. This reaction is explicitly done with heat. O NaOH, H₂O heat
What could be used as a replacement for phosphoric acid as a catalyst for the dehydration of cyclohexanol? Assume you want to avoid SN1 side reactions as much as possible. Sodium chloride Hydrobromic acid Sulfuric acid Hydrochloric acid
Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C − OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4 to form a mixture of CH3CH2CH = CH2 and the cis and trans isomers of CH3CH = CHCH3. We will see another example of this type of rearrangement in Section 18.5C.
Draw the structure(s) of the major organic product(s) of the following reaction. + 1 eq. Cl₂ Aqueous NaHCO3 0° C
Draw the structure(s) of the major organic product(s) of the following reaction. Draw a structural formula for the enol form of the carbonyl compound below.
Draw the structure(s) of the major organic product(s) of the following reaction. p-toluenesulfonic acid excess CH,CH,OH benzene
Carbonic anhydrase, an enzyme that converts carbon dioxide and water to carbonic acid as shown below, functions in the blood at an optimum pH of 7.0-7.5. Which of the following will lower the rate of carbonic anhydrase- catalyzed reaction? CO2 + H2O Carbonic anhydrase H₂CO3 O increasing the concentration of carbon dioxide O running the reaction at 4 °C carrying out the reaction at pH 7.2 O adding more carbonic anhydrase
Some elimination reactions can undergo cation rearrangements. Given the following reaction conditions, draw three possible elimination products that could form with carbocation rearrangement, or without carbocation rearrangment. Include major and minor products. Br Weak Base

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