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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Which compound below can be oxidized the greatest number of times? Oa primary alcohol Oa secondary alcohol Oa tertiary alcohol a ketone an aldehyde
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
Indicate whether the compounds below undergo racemization when treated with aqueous acid or base. Foo H3C CH₂CH₂CH3 H CH3 O yes O yes O no CH3 O no O yes On no
Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.
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
Given the organic product form in each of the following reactions draw a 3-D representation for the product molecule showing its correct configuration.

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