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Question

Explain why

The dipole moment of chlorobezene is lower than that of cyclohexyl chloride ?

alkyl halides, though polar, are immiscible with water ?

Grignard reagents should be prepared under anhydrous conditions ?

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Solution

Due to sp2 hybridization of C - atom in chlorobenzene, C-atom is more electronegative (greater s - character) whereas in cyclohexyl chloride, C - atom is sp3 hybridized, i.e., less electronegative (lesser s-character). So polarity of C - Cl bond in chlorobenzene is less than the C-Cl bond in chlorobenzene is less than the C-Cl bond in cyclohexyl chloride. Therefore, the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.

Water molecule have enough strong H - bonding (intermolecular) which is difficult to be broken by alkyl halides, though they are also polar in nature. Therefore, alkyl halides do not dissolve in water and form separate layers.

Grignard reagents (R - Mg - X) are readily decomposed by water to produce alkanes. That is why they should be prepared under anhydrous conditions. Instead, ether is used as a solvent during the preparation of Grignard reagent.


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