Explain the relative acidities.
CH₂═CHCH₂OH, CH₃CH₂CH₂OH, HC≡CCH₂OH

For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.

c.

d.

For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.

a.

b.

Rank the carbanions shown in the margin from most basic to least basic.

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b. How does the presence of an electronegative substituent such as Cl affect the acidity of a carboxylic acid?

c. How does the location of the substituent affect the acidity of the carboxylic acid?

Using the table of pK_a values given in [Appendix I] , answer the following:

d. Which is more electronegative: an sp³ oxygen or an sp² oxygen?

e. Which compounds demonstrate that the relative electronegativities of a hybridized nitrogen atom are sp > sp² > sp³?

Imidazole has two potentially basic sites (a and b). Of the two, where would you expect a proton to add preferentially?

Rationalize the rather large difference in pK_a values for the two carboxylic acids shown.

Rank the following amines in order of their basicity (strongest base = 1 ; weakest base = 6).