Predict the product of the substitution reactions, paying attention to the stereochemical outcome.

(a)

Predict the product of the substitution reactions, paying attention to the stereochemical outcome.

(b)

Predict the product of the substitution reactions, paying attention to the stereochemical outcome.

(d)

Provide a mechanism for the following S_N1 reactions that feature a rearrangement.

(a)

Provide a mechanism for the following S_N1 reactions that feature a rearrangement.

(b)

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(a)

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(b)

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(c)

Predict the product of the following substitution reactions, making sure to note whether a rearrangement should occur.

(d)

Identify the bonds that break and form in the following elimination reactions.

(a)

Identify the bonds that break and form in the following elimination reactions.

(b)

When 2-bromopropane is treated with sodium ethoxide, propene is produced. What molecule is lost from 2-bromopropane in this process?

(a) How would you convert propene to 2-bromopropane?

Practice your electron-pushing skills by drawing a mechanism for the following E2 reactions.

(a)

Practice your electron-pushing skills by drawing a mechanism for the following E2 reactions.

(b)

Practice your electron-pushing skills by drawing a mechanism for the following E1 reactions.

(a)

Practice your electron-pushing skills by drawing a mechanism for the following E1 reactions.

(b) 

Practice your electron-pushing skills by drawing a mechanism for the following E1 reactions.

(c)

Would you expect the following bases to favor E1 or E2 elimination?

(a)

Would you expect the following bases to favor E1 or E2 elimination?

(c)

Would you expect the following bases to favor E1 or E2 elimination?

(d) H₂O

Justify on a reaction coordinate diagram the fact that a strong base like sodium amide (NaNH₂) results in a faster E2 elimination than does sodium hydroxide (NaOH).

Given the reactants shown, what type of elimination would you expect to occur?

(a)

Given the reactants shown, what type of elimination would you expect to occur?

(b)

Given the reactants shown, what type of elimination would you expect to occur?

(c)

Given the reactants shown, what type of elimination would you expect to occur?

(d)

Show a mechanism for the following elimination reactions. Label the mechanism as E1 or E2.

(a)

Show a mechanism for the following elimination reactions. Label the mechanism as E1 or E2.

(c)

Show a mechanism for the following elimination reactions. Label the mechanism as E1 or E2.

(d)

Suggest an appropriate base to synthesize the alkene as the major product from the starting haloalkane.

(a)