Question #b2f20

1 Answer
Apr 19, 2017

How about this sequence?

Explanation:

#underbrace("HC≡CH")_color(red)("ethyne") + "NaNH"_2 stackrelcolor(blue)("NH"_3color(white)(m))(→) underbrace("HC≡C:"^"-""Na"^"+")_color(red)("sodium acetylide")#

#underbrace("HC≡C:"^"-""Na"^"+")_color(red)("sodium acetylide") + underbrace("CH"_3"Br")_color(red)("bromomethane") → underbrace("HC≡C-CH"_3)_color(red)("propyne")#

#underbrace("HC≡C-CH"_3)_color(red)("propyne") + "H"_2"O" stackrelcolor(blue)("Hg(OAc)"_2, "H"_2"SO"_4color(white)(mm))(→) underbrace("CH"_3"COCH"_3)_color(red)("propanone")#

#underbrace("CH"_3"COCH"_3)_color(red)("propanone") + stackrelcolor(blue)("1. CH"_3"MgBr; 2. H"_3"O"^"+"color(white)(mm))(→) underbrace(("CH"_3)_3"C-OH")_color(red)("2-methylpropan-2-ol")#

#underbrace(("CH"_3)_3"C-OH")_color(red)("2-methylpropan-2-ol") stackrelcolor(blue)("H"_2"SO"_4, Δcolor(white)(mm))(→) underbrace(("CH"_3)_2"C=CH"_2)_color(red)("2-methylpropene")#

#underbrace(("CH"_3)_2"C=CH"_2)_color(red)("2-methylpropene") + "HBr" → underbrace(("CH"_3)_3"C-Br")_color(red)("2-bromo-2-methylpropane")#