CH CH D D D: Compound K M S ×10 PK
CH CH D D D: Compound K M S ×10 PK
CH CH D D D: Compound K M S ×10 PK
CH3
D
CH3
D D O
6.5. Using data from Tables 6.1 (p. 580) and 6.2 (p. 583), estimate the extent of
deprotonation for each hydrocarbon-base combination below. Discuss the uncer-
tainties that could affect the calculation.
6.6. The rates of removal of axial and equatorial protons from 4-t-butylcyclohexanone
in NaOD/dioxane have been compared by an NMR technique. The rate of
removal of an axial proton is 5.5 times faster than for an equatorial proton. How
do you explain the difference?
6.7. The following table gives exchange rates in methanolic NaOCH3 and pK values
for some hydrocarbons. Determine if there is a correlation between the kinetic
and thermodynamic acidity.
Compound kexchange pK
M −1 s−1 ×104
X CH3