I would like help with this assignment about what haloalkanes to use as starting

Question

I would like help with this assignment about what haloalkanes to use as starting material .

See photo. (18.14)

(a) 2-chloropentane (b) 2-chlorobutane (c) chlorocyclohexane (d) isobutyl chloride 18.14 What haloalkane might you use as starting material to produce each of the following alkenes in high yield and uncontaminated by isomeric alkenes? Substitution versus elimination 18.15 The reaction of methyl iodide with sodium hydroxide give methanol always involves the SN2 mechanism. Why is SN I cannot play a role in this conversion?

Explanation / Answer

Hi,

a)  1-Bromo-1-methylcyclohaxane + Na(tertiary BuO)/tertiary BuOH would give the best yield for methylenecyclohexane

b) 4 methyl 1-pentene can be best prepared using polypropylene dimerization.

For further reading, click on following links

http://www.orgsyn.org/demo.aspx?prep=cv4p0612

http://pubs.acs.org/doi/abs/10.1021/jo01021a006

Hope this solves your problem

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