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Explain why (i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride? (ii) alkyl halides, though polar, are immiscible with water? (iii) Grignard reagents should be prepared under anhydrous conditions?

Explain why
(i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
(ii) alkyl halides, though polar, are immiscible with water?
(iii) Grignard reagents should be prepared under anhydrous conditions?

Grade:11

12 Answers

Gaurav
askIITians Faculty 164 Points
9 years ago
Hello Student
In chlorobenzene, the chlorine atom is attached to sp2chybridized carbon atom. In cyclohexyl chloride, the chlorine atom is attached to sp3 hybridized carbon atom. Hence chlorobenzene is more electronegative than cyclohexyl chloride. Therefore, the density of electrons C-Cl bond at chlorine atom is less in chlorobenzene than cyclohexyl chloride. Due to this polarity of the C-Cl bond decreases and hence dipole moment of chlorobenzene is lower than cyclohexyl chloride.
suraj kailas sonawane
22 Points
7 years ago
Hello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.
suraj kailas sonawane
22 Points
7 years ago
Hello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.best of luck..
suraj kailas sonawane
22 Points
7 years ago
Hello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.best of luck...
suraj kailas sonawane
22 Points
7 years ago
Hello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.best of luck....
ASh
62 Points
5 years ago
Hello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.
Gitanjali Rout
184 Points
5 years ago
Hello StudentIn chlorobenzene, the chlorine atom is attached to sp2chybridized carbon atom. In cyclohexyl chloride, the chlorine atom is attached to sp3 hybridized carbon atom. Hence chlorobenzene is more electronegative than cyclohexyl chloride. Therefore, the density of electrons C-Cl bond at chlorine atom is less in chlorobenzene than cyclohexyl chloride. Due to this polarity of the C-Cl bond decreases and hence dipole moment of chlorobenzene is lower than cyclohexyl chloride.
Gitanjali Rout
184 Points
5 years ago
ello student :- In benzene the hybridization of carbon in C-Cl is sp2 while the hybridization of carbon in C-Cl in cyclohexylchloride is sp3. The sp2 hybrid of C-Cl has less tendency to release electrons than the sp3hybrid of C-Cl.Therefore the points to be noted are:- (1) The magnitude of negative charge is less on chlorine atom of benzene as compared to the magnitude of negative charge of chlorine in cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.best of luck.
Gitanjali Rout
184 Points
5 years ago
cyclohexylchloride. (2) Delocalisation of lone pairs of electrons of chlorine atom over the benzene ring takes place. Therefore due to the above reasons dipole moment of chlorobenzene is lower than that of cyclohexylchloride.best of luck.
priyanka pradhan
13 Points
5 years ago
In chlorobenzene cl is bound to an sp2 hybridised carbon atom and in cyclohexylchloride cl is bound to sp3 hybridised carbon atom due to which the c-cl bond in chloro benzene is more electronegative and the bond length is less due to the partial double bond character of c-cl bond. Hence the dipole moment is lower
Abdul Jawwad
13 Points
4 years ago
The Cl atom in chlorobenzene is bonded to an sp2 hybridized carbon atom whereas the Cl atom in cyclohexyl chloride is bonded to an sp3 hybridized carbon atom. An  sp2 hybridized carbon atom with a greater s character is more electronegative and can hold electrons more tightly than an  sp3 hybridized carbon atom with a lesser s character. Thus the C-Cl bond in chlorobenzene is shorter than the C-Cl bond in cyclohexyl chloride. Since dipole moment is a product of charge and distance (here bond length), chlorobenzene having a shorter bond length will consequently have a lower dipole moment than cyclohexyl chloride.
Kushagra Madhukar
askIITians Faculty 628 Points
3 years ago
Hello Student
(i) In chlorobenzene, the chlorine atom is attached to sp2 hybridized carbon atom. In cyclohexyl chloride, the chlorine atom is attached to sp3 hybridized carbon atom. Therefore, electron density in C-Cl bond at chlorine atom is lesser in case of chlorobenzene than cyclohexyl chloride.
Due to this polarity of the C-Cl bond decreases and hence dipole moment of chlorobenzene is lower than cyclohexyl chloride.
 
(ii) Alkyl Halides are polar in nature, however to dissolve in water some energy is required to break the pre-existing hydrogen bonds between the water molecules. But, the bond between Alkyl halides and water molecule is not strong enough to provide that energy. And thus this reaction is not feasible making Alkyl Halides immiscible in water.
 
(iii) Grignard Reagents are very reactive and in the presence of moisture they react with it to give alkanes. Hence, to avoid this from happening, they are prepared under anhydrous condition.
 
Hope it Helps. 

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