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Topic: Identify compound Z, produced by the following sequence.  (Read 5414 times)

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Offline NewtoAtoms

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Identify compound Z, produced by the following sequence.
« on: January 25, 2009, 01:39:59 PM »
I am studying my notes and have begun trying to do my own examples of reactions to stay ontop of organic chemistry.

I have proposed the following questions and am wondering if anyone could proof read my logic.

1-cyclohexane-butane ---Br2 + heat----> X ---NaOCH2CH3 +heat/ethanol ---> Y ---HBr + peroxides ---> Z

My logic and leg work has brought me to the following conclusions:

                             H H  H H                                                                    H H H  H
X= (cyclohexane) ---C-C-C-C H                   OR                  (cyclohexane) ---C-C-C-C H
                             H Br H H                                                                    H H Br H

THE REASON i HAVEN'T ATTACHED Br anyone where else, is because Br is extremely regioselective so I would propose that it would only add to those two spots (place where there are secondary carbons)

                             H H  H H                                                                   H H  H  H
Y= (cyclohexane) ---C-C=C-C H                  OR                 (cyclohexane)  ---C-C=C-C H
                             H        H                                                                   H        H

Which obviously brings us to the same outcome for the double bond

Z = (cyclehexane) ---CH2CH2CHCH3
                                         l
                                         Br
The reason I have added the Br to this carbon is because it is anti-Markovnikov's therefore it would prefer to go on that carbon rather than the one previous.

I must admit I am feeling totally overwhelmed with this chapter in organic chemistry and I would be SO GRATEFUL if you could just walk through this example and help me understand it.

Thank you so much for your time.


Offline vhpk

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Re: Identify compound Z, produced by the following sequence.
« Reply #1 on: January 25, 2009, 11:57:19 PM »
Yeah, the first reaction is the free radical substitution, so can you point out which radical is the most stable.
The second one is the elimination, of course, use the Zaitsev rule to predict the product.
The last is the free radical addition, you must use the Kharasch rule or anti-Markovnikov to guess the product.
Good luck :)
Genius is a long patience

Offline aldoxime_amine

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Re: Identify compound Z, produced by the following sequence.
« Reply #2 on: January 26, 2009, 08:45:01 AM »
THE REASON i HAVEN'T ATTACHED Br anyone where else, is because Br is extremely regioselective so I would propose that it would only add to those two spots (place where there are secondary carbons)


Then why not attach it to a tertiary carbon when there is one?

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