In 3-methyl-2-cyclohexenone the eight hydrogens H a , H b , H c , and H d

Question:

In 3-methyl-2-cyclohexenone the eight hydrogens H^a, H^b, H^c, and H^d can be exchanged for deuterium in CH₃O–/CH₃OD. Ha Hb CH3

(a) Write curved-arrow mechanisms for the basecatalyzed exchange of hydrogens H^a, H^c, and H^d.

(b) Explain why hydrogen H^b is much less acidic than hydrogens H^a, H^c, and H^d, even though it is an α-hydrogen.

(c) Although hydrogen H^b is not unusually acidic, it nevertheless exchanges readily in base. Write a mechanism for the exchange of H^b.

(d) Which hydrogens of the sex hormone testosterone would be exchanged for deuterium in CH₃O–/CH₃OD? O H3C H mog CH3 m H testosterone OH

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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Question Posted: Dec 07, 2023 05:21 AM

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In 3-methyl-2-cyclohexenone the eight hydrogens H a , H b , H c , and H d

Question:

На Ha на на Hb CH3

Step by Step Answer:

a The exchange of H occurs by the usual enolateion mechanism DOCH3 CH 0 was a CH 3 CH3 CH0 CH3 CH 30 ...View the full answer

Organic Chemistry

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