1. A Review of General Chemistry

Draw the important resonance forms of the following free radicals.

(c)

(d)

Draw the important resonance forms of the following free radicals.

b.

Draw the important resonance forms of the following free radicals.

a.

Acetonitrile (CH₃C≡N) is deprotonated by very strong bases. Write resonance forms to show the stabilization of the carbanion that results.

Allylic halides have the structure

b. Draw the resonance structures of the allylic cations formed by ionization of the following halides.

(i)

(ii)

3-Bromocyclohexene is a secondary halide. It undergoes S_N1 substitution about as fast as most tertiary halides. Use resonance structures to explain this enhanced reactivity.

Are the following pairs of structures resonance contributors or different compounds?

d.

e.

Which of the following has delocalized electrons?

g.

h.

i.

Draw the resonance contributors for phenol.

Draw the resonance contributors for the phenolate ion.

Draw resonance contributors for the following ions:

d.

a. Predict the relative bond lengths of the three carbon–oxygen bonds in the carbonate ion.

b. What is the charge on each oxygen?

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

e.

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

b.

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

c.