Chapter 12: Q24E (page 354)
Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes:

Short Answer
(a)
(b)

(c)

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Chapter 12: Q24E (page 354)
Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes:

(a)
(b)

(c)

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Question: By knowing the natural abundances of minor isotopes, it’s possible to
calculate the relative heights of and M+1 peaks. If 13C has a natural
abundance of 1.10%, what are the relative heights of the and
M+1 peaks in the mass spectrum of benzene, C6H6?
Question: How might you use IR spectroscopy to distinguish between the following pairs of isomers?
Although the Diels–Alder reaction generally occurs between an electron rich diene and an electron-deficient dienophile, it is also possible to
have inverse-demand Diels–Alder reactions between suitable electrondeficient
conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one region isomer is possible, draw both.
(a)

(b)

(c)

One consequence of the base-catalyzed isomerization of unsaturated ketones described in Problem 22-55 is that 2-substituted 2-cyclopentenones can be interconverted with 5-substituted 2-cyclopentenones. Propose a mechanism for this isomerization.

The Favorskii reactioninvolves the treatment of an -bromo ketone with a base to yield a ring-contracted product. For example, the reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.

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