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Help with benzene please

Hi, I'm currently doing a preparatory worksheet for some advanced benzene mechanisms.
I'm having a bit of trouble with this question.

Explain why it is much more difficult to hydrolyse 1-chloro-4-ethyl-benzene than (1-chloro-ethyl)benzene (2)


Is it to do with the declocalised pi electrons?

Thanks for your help
Original post by Jakebarker1605
Hi, I'm currently doing a preparatory worksheet for some advanced benzene mechanisms.
I'm having a bit of trouble with this question.

Explain why it is much more difficult to hydrolyse 1-chloro-4-ethyl-benzene than (1-chloro-ethyl)benzene (2)


Is it to do with the declocalised pi electrons?

Thanks for your help

Heya, I'm going to put this in the Chemistry forum for you as you should get more responses there.:smile:

You should also check out the forum to see if there's any other threads there which might be helpful to you! http://www.thestudentroom.co.uk/forumdisplay.php?f=130
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Original post by Puddles the Monkey
Heya, I'm going to put this in the Chemistry forum for you as you should get more responses there.:smile:

You should also check out the forum to see if there's any other threads there which might be helpful to you! http://www.thestudentroom.co.uk/forumdisplay.php?f=130
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Thank you! yes, i did post in the chemistry section as well in the end:biggrin:
Original post by Jakebarker1605
Hi, I'm currently doing a preparatory worksheet for some advanced benzene mechanisms.
I'm having a bit of trouble with this question.

Explain why it is much more difficult to hydrolyse 1-chloro-4-ethyl-benzene than (1-chloro-ethyl)benzene (2)


Is it to do with the declocalised pi electrons?

Thanks for your help


Draw them out. Think of the mechanism. In one case the Cl is attached to an sp3 carbon whereas in the other it is attatched to an sp2 carbon which makes up the benzene ring.

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