Question

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 as the base, the more highly substituted alkene product predominates....

When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 as the base, the more
highly substituted alkene product predominates. When KOC(CH3)3 is used as the base,
the less highly substituted alkene predominates. Give the structures of the two
products and offer an explanation.
The major product which results when 2-chloropentane is heated in sodium iodide
is an ether. Show and name the mechanism by which this ether forms.

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Answer #1

Solution:

>> When 1-iodo-1-methylcyclohexane is treated with sodium ethoxide (NaOC2H5) base, then more substituted product is formed by removal of proton from the ring carbon and product is the satzeff product.

When treated with a highly hindered KOC(CH3)3 base, then product is formed by removal of proton from less hindered methyl substituent and Hoffmann product is formed.

The complete mechanism is given below.

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