In 3-methyl-2-cyclohexenone the eight hydrogens Ha, Hb , Hc , and Hd can be exchanged

Chapter 22, Problem 22.72

(choose chapter or problem)

In 3-methyl-2-cyclohexenone the eight hydrogens Ha, Hb , Hc , and Hd can be exchanged for deuterium in CH3O/CH3OD. (a) Write curved-arrow mechanisms for the basecatalyzed exchange of hydrogens Ha, Hc , and Hd . (b) Explain why hydrogen Hb is much less acidic than hydrogens Ha, Hc , and Hd, even though it is an a-hydrogen. (c) Although hydrogen Hb is not unusually acidic, it nevertheless exchanges readily in base. Write a mechanism for the exchange of Hb . (Hint: Consider the equilibrium in 22.73.) (d) Which hydrogens of the sex hormone testosterone would be exchanged for deuterium in CH3O/CH3OD?

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