Question

An alkyl bromide produces a single alkene when it reacts with sodium ethoxide and ethanol. This alkene undergoes hydrogenation and produces 2-methyl butane. What is the identity of the alkyl bromide.

• A. 1-bromo-2, 2-dimethylpropane
• B. 1-bromobutane
• C. 1-bromo-2-methylbutane
• D. 2-bromo-2-methylbutane (e) 2-bromopentane

Answer 1

Answer: (C)

1-bromo-2-methylbutane

Answer 2

$\underset{\text{1, bromo, 2 methyl butane}}{CH_{3} - CH_{2} - \overset{CH_{3}}{\overset{|}{C} ⥂ H -}CH_{2}Br} + C_{2}H_{5}ONa\overset{\quad C_{2}H_{5}OH\quad}{\rightarrow}$

$CH_{3} - CH_{2} - \overset{CH_{3}\mspace{6mu}\mspace{6mu}\mspace{6mu}\mspace{6mu}\mspace{6mu}}{\overset{|}{C} = CH_{2}} + NaBr + C_{2}H_{5}OH\underset{(\text{Hydrogenation})}{\overset{\quad + H_{2}\quad}{\rightarrow}}$

$\underset{\text{2 methyl butane}}{CH_{3} - CH_{2} - \overset{CH_{3}}{\overset{|}{C} ⥂ H -}CH_{3}}$