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Which of the following compounds has the highest boiling point?
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1177 Upvotes
Verified Answer
The correct answer is:
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl}$
For the same halogen, boiling point of alkyl halide decreases as the size of the alkyl group decreases.
For isomeric alkyl halides, boiling point decreases as branching increases. So the decreasing order of boiling point is
$$
\begin{aligned}
& \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl}>\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl} \\
&>\mathrm{CH}_3 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{CH}_2 \mathrm{Cl}>\left(\mathrm{CH}_3\right)_3 \mathrm{CCl} .
\end{aligned}
$$
For isomeric alkyl halides, boiling point decreases as branching increases. So the decreasing order of boiling point is
$$
\begin{aligned}
& \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl}>\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Cl} \\
&>\mathrm{CH}_3 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{CH}_2 \mathrm{Cl}>\left(\mathrm{CH}_3\right)_3 \mathrm{CCl} .
\end{aligned}
$$
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