Chapter 8: Q83P (page 378)
Which of the following is the strongest acid?
Chapter 8: Q83P (page 378)
Which of the following is the strongest acid?
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Get started for freeExplain why the pka of p-nitrophenol is 7.14, whereas the pka of m-nitrophenol is 8.39.
Which compound would you expect to have the greater heat of hydrogenation: 1,2-pentadiene or 1,4-pentadiene?
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.)
The triphenylmethyl cation is so stable that a salt such as triphenylmethyl chloride can be isolated and stored. Why is this carbocation so stable?
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?
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