Learning Group Problem - Chapter Four
Draw the structure of 1-methylpropylcyclohexane in both a condensed
structural formula and a bond line formula.
Provide another acceptable IUPAC name for this compound.
Draw the structure in its lowest energy chair conformation.
Devise at least six syntheses for 1-methylpropylcyclohexane starting with
alkyl halides (cyclic, acyclic, vinyl, or alkenyl). Make each synthesis
as different from every other of the six as possible (within reason).
Approach the problem by first showing the retrosynthetic pathway for each
route. For the synthetic (forward direction) show all steps and reagents
(not mechanisms). Be sure to employ examples somewhere in your six
syntheses that use each of the three reaction types presented in section
4.15 (A. hydrogenation of alkyl halides, B. reduction of alkyl halides,
and C. lithium dialkylcuprate reactions). Include carbon-carbon bond
forming steps in at least four of the syntheses.
Ciao for now,
CBF
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Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055
Associate Professor Email fryhle@u.washington.edu
Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html
Pacific Lutheran University
Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^
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