Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH₃ 2. NaOH, H₂O₂ (ii) 1. Hg(OAc)₂ 2. NaBH₄ (iii) H₂SO₄ , H₂O (iv) 1. OsO₄ 2. NaHSO₃ (v) H₂O (vi) NaOH, H₂O . If there is no reaction, write 'no reaction.'

(d)

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H₂O; (vi) NaOH, H₂O. If there is no reaction, write 'no reaction.'

(f)

Predict the product for each of the following reactions.

(a)

Predict the product for each of the following reactions.

(b)

Predict the product for each of the following reactions.

(c)

Predict the product for each of the following reactions.

(d)

Identify whether each of the following reactions proceed by an S_N1 ,S_N2 , E1, or E2 mechanism.

(a)

Identify whether each of the following reactions proceed by an S_N1, S_N2, E1, or E2 mechanism.

(b)

Identify whether each of the following reactions proceed by an S_N1, S_N2, E1, or E2 mechanism.

(c)

A trifluoromethanesulfonate (triflate) can be used in a manner similar to tosylates. Which would you expect to be a better leaving group? Why?

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(a)

Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.

(b)

(a) Show how you would affect the following transformation using a tosylate.

(b) Why might this not be the most sustainable method?

(c) What reagent might you use instead?

Predict the product of the following reactions.

(a)

Predict the product of the following reactions.

(b)

Predict the product of the following reactions.

(c)

A graduate student attempted the following reaction and did not isolate the expected product.

(a) What product did they isolate?

(b) What reagent should they have used instead to get their desired product?

Suggest the appropriate reagents to carry out the following transformations.

(a)

Suggest the appropriate reagents to carry out the following transformations.

(b)

Suggest the appropriate reagents to carry out the following transformations.

(c)

Suggest the appropriate reagents to carry out the following transformations.

(d)

Suggest the appropriate reagents to carry out the following transformations.

(e)

Suggest the appropriate reagents to carry out the following transformations.

(f)

Suggest the appropriate reagents to carry out the following transformations.

(g)

Draw a reaction coordinate diagram for the following transformation. Label all product, intermediates, and substrates.

Produce a mechanism for the following transformation.

Predict the product for the acid-catalyzed pinacol rearrangement of the following diols.

(a)

Draw the mechanism for the acid-catalyzed pinacol rearrangement of the following diols.

(a)

Predict the product for the acid-catalyzed pinacol rearrangement of the following diols.

(b)

Draw the mechanism for the acid-catalyzed pinacol rearrangement of the following diols.

(b)