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Chapter 8: 8-102P (page 380)

a) Propose a mechanism for the following reaction:

b) What is the product of the following reaction?

Short Answer

Expert verified

6,6-dimethylcyclohexa-2,4-dienone reacts with acid undergoes rearrangement to form a 2,3-dimethylphenol.

The carbonyl oxygen donates lone pair of electrons to proton form a positively charged oxygen atom.

Step by step solution

01

How the reaction proceed

6,6-dimethylcyclohexa-2,4-dienone reacts with acid undergoes rearrangement to form a 2,3-dimethylphenol.

The carbonyl oxygen donates lone pair of electrons to proton form a positively charged oxygen atom.

02

Final answer

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Most popular questions from this chapter

Refer to the electrostatic potential maps on p. 368 to answer the following questions:

a. Why is the bottom part of the electrostatic potential map of pyrrole blue?

b. Why is the bottom part of the electrostatic potential map of pyridine red?

c. Why is the center of the electrostatic potential map of benzene more red than the center of the electrostatic

potential map of pyridine?

What two sets of a conjugated diene and a dienophile could be used to prepare the following compound?

Which compound would you expect to have the greater heat of hydrogenation: 1,2-pentadiene or 1,4-pentadiene?

Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.

a. Predict the relative bond lengths of the three carbon-oxygen bonds in carbonate ion.

b. What is the charge on each oxygen?
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