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Chapter 8: Q87P (page 379)

How could you synthesize the following compound from starting materials containing no more than six carbons? (Hint: A 1,6-diketone can be synthesized by oxidative cleavage of a 1,2-disubstituted cyclohexene.)

Short Answer

Expert verified

A process when a carbon-carbon bond is broken and the carbons that made up the bond are simultaneously oxidised. A reaction of oxidative cleavage is alkyne ozonolysis.

Step by step solution

01

Definition ofoxidative cleavage-

A process when a carbon-carbon bond is broken and the carbons that made up the bond are simultaneously oxidised. A reaction of oxidative cleavage is alkyne ozonolysis.

02

Step 2

A 1,6-diketone can be synthesized by oxidative cleavage of a 1,2-disubstituted cyclohexene.

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Most popular questions from this chapter

The acid dissociation constant (Ka) for loss of a proton from cyclohexanol is 1 ×10-16.

a. Draw a reaction coordinate diagram for loss of a proton from cyclohexanol.

b. Draw the resonance contributors for phenol.

c. Draw the resonance contributors for the phenolate ion.

d. On the same plot with the energy diagram for loss of a proton from cyclohexanol, draw an energy diagram for loss of a proton from phenol.

e. Which has a greater Ka: cyclohexanol or phenol?

f. Which is a stronger acid: cyclohexanol or phenol?

a) Propose a mechanism for the following reaction:

b) What is the product of the following reaction?

While attempting to recrystallize maleic anhydride, a student dissolved it in freshly distilled cyclopentadiene rather than in freshly distilled cyclopentane. Was his recrystallization successful?

Which species in each pair is more stable?

Rank the indicated hydrogen in the following compounds from most acidic to least acidic:
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