COMEDK · Chemistry · 25. Haloalkanes and Haloarenes

Arrange the following in the order of increasing reactivity towards \(\mathrm{SN}_{\mathrm{2}}\) reactions.
\(\begin{array}{ll}
\left(\mathrm{CH}_3\right)_3 \mathrm{CCH}_2 \mathrm{Br}(\mathrm{P}) ; & \\\mathrm{CH}_3\left(\mathrm{CH}_2\right)_3 \mathrm{Br}(\mathrm{Q}) ; &\\
\mathrm{CH}_3 \mathrm{CH}_2-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_2 \mathrm{Br}(\mathrm{R}) ; & \\\left(\mathrm{CH}_3\right)_2 \mathrm{CHCH}_2 \mathrm{CH}_2 \mathrm{Br}(\mathrm{S})
\end{array}\)

A \(\mathrm{R}<\mathrm{P}<\mathrm{Q}<\mathrm{S}\)
B \(\mathrm{P}<\mathrm{R}<\mathrm{S}<\mathrm{Q}\)
C \(\mathrm{Q}<\mathrm{S}<\mathrm{R}<\mathrm{P}\)
D \(\mathrm{P}<\mathrm{Q}<\mathrm{R}<\mathrm{S}\)

Verified Solution

Answer & Solution

Correct Answer

(B) \(\mathrm{P}<\mathrm{R}<\mathrm{S}<\mathrm{Q}\)

Step-by-step Solution

Detailed explanation

\(S_N2\) reactivity decreases with increasing steric hindrance around the carbon bearing the leaving group. P: \((CH_3)_3CCH_2Br\) (neopentyl bromide) — branching at \(\beta\)-carbon with three bulky methyl groups \(\Rightarrow\) most hindered, least reactive. R:…

Apply the relevant identity from the chapter and substitute the values established in the previous step, keeping the original constraint in view.

Use the simplified expression to isolate the unknown, then plug the result back into the question setup to confirm the working is internally consistent.

Cross-check against a boundary or limiting case. Both the dimensional balance and the qualitative behaviour at the extreme should agree with the candidate answer.

Combine the steps above to identify the correct option. The remaining choices each fail at least one of the consistency, dimensional, or boundary checks.

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