What is the correct order of reagents needed for the following transformation? Write the correct sequence #CH_3-CH_2CH_2Br -> CH_3-CH_2-CH_2-S-CH_2-CH(CH_3)_2 #

1 Answer
Jan 22, 2016

Answer:

How about this sequence?

Explanation:

#"CH"_3"CH"_2"CH"_2"Br" stackrelcolor(blue)("alcoholic KOH"color(white)(X))(→) "CH"_3"CH=CH"_2 stackrelcolor(blue)("HBr"color(white)(X))(→) ("CH"_3)_2"CHBr"#

#"CH"_3"CH=CH"_2 stackrelcolor(blue)("1. O"_3"; 2. Zn/HOAc"color(white)(X))(→) "CH"_2"O"#

#("CH"_3)_2"CHBr"stackrelcolor(blue)("Mg, dry ether"color(white)(X))(→) ("CH"_3)_2"CHMgBr" stackrelcolor(blue)("1. CH"_2"O; 2. H"^(+)color(white)(X))(→)("CH"_3)_2"CHCH"_2"OH"#

#("CH"_3)_2"CHCH"_2"OH"stackrelcolor(blue)("PBr"_3color(white)(X))→ ("CH"_3)_2"CHCH"_2"Br"#

#("CH"_3)_2"CHCH"_2"Br"stackrelcolor(blue)("NaSH"color(white)(X))(→) ("CH"_3)_2"CHCH"_2"SH"stackrelcolor(blue)("NaH"color(white)(X))(→)("CH"_3)_2"CHCH"_2"S"^(-)#

#("CH"_3)_2"CHCH"_2"S"^(-)stackrelcolor(blue)("CH"_3"CH"_2"CH"_2"Br"color(white)(X))(→)("CH"_3)_2"CHCH"_2"SCH"_2"CH"_2"CH"_3#