Which of the following carbocations would you expect to rearrange?

Protonation of which of the following alkenes would be faster?

Which of the following indicated atoms would you expect to be most basic?

(a)

Which of the following indicated atoms would you expect to be most basic?

(b)

Which of the following indicated atoms would you expect to be most basic?

(c)

What is the role of a solvent in a chemical reaction? What happens to the solvent at the end of a reaction?

Given that step 1 of the following reaction is rate determining, write the rate law for the overall reaction.

For the following molecule, draw the Newman projection (around the 2,3-bond) with a dihedral angle of 180° between the bromine and hydrogen.

In the following reactions, identify the bonds formed and the bonds broken.

(a)

In the following reactions, identify the bonds formed and the bonds broken.

(c)

Based on your answer to Assessment 12.8, which bases would you expect to be good leaving groups?

Given the following rate data, how many molecules are in the rate-determining step of this reaction?

Practice your electron-pushing skills by drawing a mechanism for the following S_N2 reactions.

(a)

Practice your electron-pushing skills by drawing a mechanism for the following S_N2 reactions.

(b)

Practice your electron-pushing skills by drawing a mechanism for the following S_N2 reactions.

(c)

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(a)

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(b)

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(c)

For which of the following reactions would you expect elimination to be more favored than substitution?

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vs.

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Which of the following S_N2 reactions should proceed at a faster rate? Justify your answer on a reaction coordinate diagram.

Which of the following S_N1 reactions should proceed at a faster rate? Justify your answer on a reaction coordinate diagram.

The allylic bromide below gives two S_N1 products. Justify the formation of each.

Even with an excess of cyanide, only one equivalent will react with the following dibromoalkane. To which carbon will the cyanide add? Predict the product and explain your choice.

Order the following molecules on the basis of their nucleophilic strength using the pKₐ values of their conjugate acids.

For each pair, choose the more reactive nucleophile.

(a)

For each pair, choose the more reactive nucleophile.

(b)

Which S_N2 reaction would you expect to be faster? Explain your answer.

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(a)

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(b) F^-

Would the following nucleophiles be more likely to participate in an S_N1 or S_N2 reaction?

(c)