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Haloalkanes and Haloarenes — Chemistry STD 12 Science — Question

Gujarat BoardEnglish MediumSTD 12 ScienceChemistryHaloalkanes and Haloarenes3 Marks
Question
Answer the following questions:
An optically active compound having molecular formula C7H15Br reacts with aqueous KOH to give a racemic mixture of products. Write the mechanism involved in this reaction.
✓

Answer

Since the optically active compound, C7H15Br reacts with KOH forms a racemic mixture, therefore it must be tertiary alkyl halide and the reaction will follow SN1 mechanism.

$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{C}-\text{CH}_2-\text{CH}_3+\text{OH}^-\rightarrow\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Br}$

$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{C}-\text{CH}_2-\text{CH}_3+\text{Br}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{(\pm)\text{3-Methyl-hexam-3-ol}}$

Mechansim:

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