Re: ORGLIST: methyl cyclohexene from methyl cyclohexanone

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From: Jacob Zabicky (Jacob.Zabicky$##$uab.es)
Date: Mon Jan 04 1904 - 21:20:08 EST


Dear Juana,

Your question can have variuos replies, depending on who answers and on the
point of view.

A chemist dealing with reaction mechanisms may propose several steps, where
only the slowest are in control of your results, but you cannot avoid
passing through the fastest, lest your results differ from the desired ones.

A chemical engineer may speak about a "unit process," according to which
you observe what are you putting in your reactor and what are you getting
out of it. If you devise a contraption where starting from cyclohexanone
and other reagents, you get methylcyclohexene whithout need of separating
or adding other reagents at some intermediate stage, then you have what an
organic synthesist may call a "one-step-reaction." This situation, however,
need not be the best for the usual synthetic methods of organic chemistry,
which are batch processes undertaken in a liquid matrix, between the normal
melting and boiling points of the liquid phases. An industrial route may
involve gaseous reagents continuously flowing over a multifunctional
catalyst bed.

Your case, for example, may probably be better served in the laboratory by
a route including the Grignard reaction and an intermediary tertiary
alcohol, whether you isolate it or not. Whether you get an exo- or an
endo-cyclic water elimination from the intermediate alcohol depends on the
structure of the cyclic group. If you start from cyclohexanone you'll
probably get 1-methylcyclohexene, however, if your starting ketone is
cyclopentanone, your end product may be 1-methylenecyclopentane.

All the best,

Jacob Zabicky

>Hello
>I will like to synthetize methyl cyclohexane from methyl cyclohexanone. I
>will like to know if it is posible to do in just one step.I would greatly
>appreciate anyone who can point me to good references on this, because I
>have searched in some books with no success.
>Thank you
>
>Juana L.
>
>
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