Organic Compounds Containing Halogens Question 135

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

[Kerala PMT 2004]

Options:

A) 1-bromo-2, 2-dimethylpropane

B) 1-bromobutane

C) 1-bromo-2-methylbutane

D) 2-bromo-2-methylbutane

E) 2-bromopentane

Show Answer

Answer:

Correct Answer: C

Solution:

$ \underset{\text{1, bromo, 2 methyl butane}}{\mathop{CH_3-CH_2-\overset{CH_3}{\mathop{\overset{|}{\mathop{C}}H-}}CH_2Br}}+C_2H_5ONa\xrightarrow{C_2H_5OH} CH_3-CH_2-\overset{CH_3\ \ \ \ \ }{\mathop{\overset{|}{\mathop{C}}=CH_2}}+NaBr+C_2H_5OH\underset{\text{(Hydrogenation)}}{\mathop{\xrightarrow{+H_2}}} $

$ \underset{\text{2 methyl butane}}{\mathop{CH_3-CH_2-\overset{CH_3}{\mathop{\overset{|}{\mathop{C}}H-}}CH_3}} $