Question: Draw a stepwise mechanism for the following reaction, which results in ring expansion of a six-membered ring to a seven-membered ring.
The carbocations generated by the addition of acids to alkenes may undergo shifting (1,2-hydrogen or 1,2-methyl), depending upon their stability.
The stability order of the carbocations is .
The stability of carbocations enables 1,2-hydrogen and methyl shift. After the shifting of methyl and hydrogen to adjacent positions, which is the most stable carbocation.
The reaction of the given compound with water and sulfuric acid proceeds via 1,2-bond shift to generate a carbocation. The carbocation gives a tertiary alcohol product.
The mechanism is shown below:
Question: Although naturally occurring unsaturated fatty acids generally have the Z configuration, elaidic acid, a C18 fatty acid having an E double bond, is present in processed foods such as margarine and cooking oils. Predict how the melting point of elaidic acid compares with the melting points of stearic and oleic acids (Table 10.2).
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