Question #b9441

1 Answer
Jan 1, 2018

How about this?

Explanation:

Step 1. Ozonolysis

#underbrace("CH"_2"=C"("CH"_3)"CH"_2"CH"_2"CH"_3)_color(red)("2-methylpent-1-ene") stackrelcolor(blue)("1. O"_3; "2. Zn/HOAc"color(white)(mm))(→) underbrace("CH"_3"C(=O)CH"_2"CH"_2"CH"_3)_color(red)("pentan-2-one")#

Step 2. Catalytic hydrogenation of the ketone

#"CH"_3"C(=O)CH"_2"CH"_2"CH"_3 stackrelcolor(blue)("H"_2"/Ni"color(white)(mm))(→) underbrace("CH"_3"CH(OH)CH"_2"CH"_2"CH"_3)_color(red)("pentan-2-ol")#

Step 3. Acid-catalyzed dehydration of the alcohol

#"CH"_3"CH(OH)CH"_2"CH"_2"CH"_3 stackrelcolor(blue)("H"_2"SO"_4, Δ color(white)(mm))(→) underbrace("CH"_3"CH=CH"_2"CH"_2"CH"_3)_color(red)("pent-2-ene")#