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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 88a(vi)
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (vi) NaOH, H2O . If there is no reaction, write 'no reaction.'
(a)
Problem 88d
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)
Problem 88f(v,vi)
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)
Problem 89a
Predict the product for each of the following reactions.
(a)
Problem 89b
Predict the product for each of the following reactions.
(b)
Problem 89c
Predict the product for each of the following reactions.
(c)
Problem 89d
Predict the product for each of the following reactions.
(d)
Problem 90a
Identify whether each of the following reactions proceed by an SN1 ,SN2 , E1, or E2 mechanism.
(a)
Problem 90b
Identify whether each of the following reactions proceed by an SN1, SN2, E1, or E2 mechanism.
(b)
Problem 90c
Identify whether each of the following reactions proceed by an SN1, SN2, E1, or E2 mechanism.
(c)
Problem 91
A trifluoromethanesulfonate (triflate) can be used in a manner similar to tosylates. Which would you expect to be a better leaving group? Why?
Problem 92a
Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.
(a)
Problem 92b
Using an appropriate tosylate intermediate, synthesize the following molecules starting from the appropriate alcohol.
(b)
Problem 93
(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?
Problem 94a
Predict the product of the following reactions.
(a)
Problem 94b
Predict the product of the following reactions.
(b)
Problem 94c
Predict the product of the following reactions.
(c)
Problem 96
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?
Problem 97a
Suggest the appropriate reagents to carry out the following transformations.
(a)
Problem 97b
Suggest the appropriate reagents to carry out the following transformations.
(b)
Problem 97c
Suggest the appropriate reagents to carry out the following transformations.
(c)
Problem 97d
Suggest the appropriate reagents to carry out the following transformations.
(d)
Problem 97e
Suggest the appropriate reagents to carry out the following transformations.
(e)
Problem 97f
Suggest the appropriate reagents to carry out the following transformations.
(f)
Problem 97g
Suggest the appropriate reagents to carry out the following transformations.
(g)
Problem 98
Draw a reaction coordinate diagram for the following transformation. Label all product, intermediates, and substrates.
Problem 99
Produce a mechanism for the following transformation.
Problem 100a(i)
Predict the product for the acid-catalyzed pinacol rearrangement of the following diols.
(a)
Problem 100a(ii)
Draw the mechanism for the acid-catalyzed pinacol rearrangement of the following diols.
(a)
Problem 100b(i)
Predict the product for the acid-catalyzed pinacol rearrangement of the following diols.
(b)
