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Topic: Addition of HCl to 2-methyl-1,3-cyclohexadiene  (Read 273 times)

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Offline ve_90

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Addition of HCl to 2-methyl-1,3-cyclohexadiene
« on: March 18, 2025, 12:52:23 PM »
1) I add the proton to the C1-C2 double bond: I obtain a tertiary allylic carbocation and a secondary carbocation.
2) I add the proton to the C3-C4 double bond: I obtain a secondary carbocation and a secondary allylic carbocation.
3) The chloride ion bonds to the tertiary allylic carbocations stabilized by resonance from point 1: I obtain 3-chloro-3-methylcyclohexene and 3-chloro-1-methylcyclohexene.
These are the 1,2- and 1,4-addition products (can someone help me understand how I can distinguish them in this way?).
4) The chloride ion bonds to the secondary allylic carbocations stabilized by resonance from point 2: I obtain 6-chloro-1-methylcyclohexene (Is this the correct IUPAC name?). What type of products are these? 1,2 or 1,4?

I was also asked which of the four products are formed in the greatest quantity and why. I believe that 3-chloro-3-methylcyclohexene and 3-chloro-1-methylcyclohexene are formed in the greatest quantity because they are produced through the most stable intermediates. Am I correct? Do the other products not form at all, or do they form in larger quantities?

I really appreciate all the responses, they were very helpful! Thanks for your support!

Offline ve_90

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Re: Addition of HCl to 2-methyl-1,3-cyclohexadiene
« Reply #1 on: March 19, 2025, 12:33:28 PM »
Can’t anyone help me?

Offline Meter

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Re: Addition of HCl to 2-methyl-1,3-cyclohexadiene
« Reply #2 on: March 25, 2025, 03:30:38 AM »
You need to draw your attempts. No one is going to decipher your text.

Offline Borek

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Re: Addition of HCl to 2-methyl-1,3-cyclohexadiene
« Reply #3 on: March 25, 2025, 05:57:51 PM »
Note: you can post molecules using SMILES (see https://www.chemicalforums.com/index.php?topic=59314.0)
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