Chapter 8: 8-100P (page 380)
Cyclopentadiene can react with itself in a Diels–Alder reaction. Draw the endo and exo products.
Short Answer
We have to draw endo and exo products of cyclopentadiene:

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Chapter 8: 8-100P (page 380)
Cyclopentadiene can react with itself in a Diels–Alder reaction. Draw the endo and exo products.
We have to draw endo and exo products of cyclopentadiene:

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Which species in each pair is more stable?
What diene and what dienophile should be used to synthesize the following?

a. The following compounds have the same molecular formula as benzene. How many monosubstituted products would each have?
1.±á°ä≡C°ä≡C°ä±á2CH3 2. CH2≡C±á°ä≡C°ä±á≡C±á2
b. How many disubstituted products would each of the preceding compounds have? (Do not include stereoisomers.)
c. How many disubstituted products would each of the compounds have if stereoisomers are included?
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?
Protonated cyclohexylamine has aKa=1×10−11. Using the same sequence of steps as in Problem 94 , determine which is a stronger base, cyclohexylamine or aniline.

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