Carbanons are very useful nucleophiles in organic synthesis. In general, C-H Bonds are not strongly acidic. However, certain C-H groups can be deprotonated with alkoxide and amide bases.

Using the pKa values from Table 1.8 (http://courses.ncsu.edu/ch221/lec/001/CareyTable1.8.pdf), estimate the position of the following proton transfer equilibria. Please show your work. If you use scientific notation, remember to use only integer exponenets. Your answer must be within a factor of 5 of the correct value to receive credit. The counterions have been omitted from these equilibria for simplicity.

Question

Carbanons are very useful nucleophiles in organic synthesis. In general, C-H Bonds are not strongly acidic. However, certain C-H groups can be deprotonated with alkoxide and amide bases.

Using the pKa values from Table 1.8 (http://courses.ncsu.edu/ch221/lec/001/CareyTable1.8.pdf), estimate the position of the following proton transfer equilibria. Please show your work. If you use scientific notation, remember to use only integer exponenets. Your answer must be within a factor of 5 of the correct value to receive credit. The counterions have been omitted from these equilibria for simplicity.

anonymous · Answer

Equations: http://www.imagebam.com/image/dc5893210037551 ^ "Note: For this alkyne, and for the aldehyde shown in the same problem, use the closest pKa value you can find in the pKa tables." How should I go about solving this problem???