The structure of an adamantyl cation, shown below, was determined by X-Raycrystallography. Some of the bonds were found to be significantly longer thannormal. Using your knowledge of stabilisation of carbenium ions byhyperconjugation, select which bond was unusually long (for clarity only one of eachtype of bond is labelled).ABond aBond bBond cO Bond d+Bbd Triphenylmethyl (trityl) groups are often used for the protection of alcohols becausethey are easily removed, as shown below. Think about the likely mechanism of thishydrolysis and then predict where the isotopic label would appear in the products if18OH, was used.○PhPhPhH₂OEtOHLOHR-In the Ph,COHIn the ROHIn both the Ph.COH and the ROHIn neither the Ph,COH nor the ROH+HOPhPhPh

To answer this question we need the concept of cabocation. In adementyl system which is very…

Triphenylmethyl (trityl) groups are often used for the protection of alcohols because they are easily removed, as shown below. Think about the likely mechanism of this hydrolysis and then predict where the isotopic label would appear in the products if 18OH₂ was used. R hot Ph Ph -Ph H₂O EtOH LOH In the Ph,COH In the ROH In both the Ph,COH and the ROH In neither the Ph,COH nor the ROH + Ph offen Ph Ph HO

Triphenylmethyl (trityl) groups are often used for the protection of alcohols because they are easily removed, as shown below. Think about the likely mechanism of this hydrolysis and then predict where the isotopic label would appear in the products if 18OH₂ was used. R hot Ph Ph -Ph H₂O EtOH LOH In the Ph,COH In the ROH In both the Ph,COH and the ROH In neither the Ph,COH nor the ROH + Ph offen Ph Ph HO

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter14: Mass Spectrometry

Section: Chapter Questions

Problem 14.13P

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