Question

Which will form 2,2-dibromopropane with $HBr$?

• A. $C{H}_2=CH-C{H}_3$
• B. $C{H}_3-C\equiv CH$
• C. $C{H}_3-\underset{Br}{\underset{|}{C}}=C{H}_2$
• D. Both B and C

Answer 1

The correct option is D Both B and C

The reaction will go through Markovnikov addition pathway where $Br$ will attach to more substituted carbon and forms geminal dibromide.
$C{H}_3-C\equiv CH\stackrel{HBr}{⟶}C{H}_3-\underset{Br}{\underset{|}{C}}=C{H}_2\stackrel{HBr}{⟶}C{H}_3-\stackrel{Br}{\stackrel{|}{\underset{Br}{\underset{|}{C}}}}-C{H}_3$