AL org chem (頭幾課)

2010-10-25 4:12 am

回答 (1)

2010-10-25 7:09 am
✔ 最佳答案
addition of HCl to alkene, followed by friedal-craft reaction: substitution on benzene ring.

A:
CH3(CH2)9CH-C6H5
         |
         CH3
reaction involves addition of HCl to alkene, forming secondary chloroalkane;
normal friedal-craft addition to benzene ring.

B:
CH3-(CH2)9-CH(CH3)-C6H4-SO3H
sulphonation at 4-position (para-) occurs.

3-position (meta-) is not favorable as delocalization of positive charge on intermediate cannot go to the C with alkyl group attached.
alkyl group has electron-donating effect. if the positive charge can go to that carbon by resonance, the structure is stabilized and reaction is more favorable.

2- and 4- position is more favorable due to resonance stabilization.
however, approach of sulphur trioxide to 2-position (ortho-) is hindered by the bulky alkyl group.


C: simple neutralization. write it yourself.


You'll find an artificial detergent (alkylbenzenesulphonate) learnt in CE chem.


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