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10. Addition Reactions

Oxymercuration

10. Addition Reactions

Oxymercuration

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General properties of oxymercuration-reduction.

General properties of oxymercuration-reduction.

Johnny Betancourt

Acid-catalyzed oxymercuration-reduction mechanism

Acid-catalyzed oxymercuration-reduction mechanism

Johnny Betancourt

Practice this topic

Multiple Choice

Predict the product of the following reaction.

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate. p.

Textbook Question

Predict the major products of the following reactions. a. 1−methylcyclohexene+ aqueous Hg(OAc)2 b. the product from part (a), treated with NaBH4

Textbook Question

a. Propose a mechanism for the following reaction. CH3C(CH3)=CHCH3 Hg(OAc)2, CH3CH2OH—> (90%) (CH3)2C(CH3CH2O)CH(Hg(OAc))CH3 b. Give the structure of the product that results when this intermediate is reduced by sodium borohydride.

Textbook Question

Show how you would accomplish the following transformations. a.

Textbook Question

The first step of oxymercuration–reduction is stereospecific, and yet this fact wasn't emphasized in that discussion. Show the stereospecificity of the first step for the following alkene and then explain why the stereospecificity becomes unimportant after the second step. ?

Textbook Question

Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)₂ , H₂O 2. NaBH₄ ]. (b)

Textbook Question

(••••) A common situation occurs when both carbons of the mercurinium ion are secondary. In a situation like the one shown, to which carbon would you expect water to add? That is, would you expect to produce A or B? Explain your answer.

Textbook Question

Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.

Textbook Question

Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.

Textbook Question

Which is more stable, a carbocation or a mercurinium ion? How do you know? vs

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (ii) 1. Hg(OAc)₂ , H₂O , 2. NaBH₄ (a)

Textbook Question

(•) Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄ (g)

Textbook Question

(•) Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄ (k)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers? (a)

Textbook Question

(••) At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules. (h)

Textbook Question

(••) For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vi) H₂SO₄, HgSO₄, H₂O. If you expect two products, show both. (c)

Textbook Question

(••) Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.' (a)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses. (d)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(c) <IMAGE>

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(a) <IMAGE>

Textbook Question

(••) IN THE CHEMICAL LITERATURE In 1973, Caine and Tuller reported a synthesis of racemic oplapanone, a sesquiterpene isolated from Oplopanax japonicus (a deciduous shrub) involving a reaction we learned in this chapter. Predict the product of the reaction shown. (Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663.)

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Textbook Question

(••••) LOOKING BACK Assessment 8.74 revealed that oxymercuration could be used to make cyclic esters. Suggest a likely mechanism for this transformation.

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Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.

(b) <IMAGE>

Textbook Question

(••••) FROM THE LITERATURE The formation of five-membered ring ethers is an important goal in synthetic organic chemistry because tetrahydrofurans are contained within a number of antitumor natural products. Toward that end, a one-pot synthesis of a bis-THF containing compound was developed (Eur. J. Org. Chem. 2010, 6263–6268). Suggest a mechanism for this transformation.

<IMAGE>

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material. <IMAGE>

a. <IMAGE>

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 3−methylpent−1−ene→3−methylpentan−2−ol

Explain why acid-catalyzed hydration would be a poor choice for the reaction in (c).

Textbook Question

Predict the major products of the following reactions.

c. 4−chlorocycloheptene+ Hg(OAc)2 in CH3OH

d. the product from part (c), treated with NaBH4

Textbook Question

Show how you would accomplish the following synthetic conversions.

a. but−1−ene→ 2−methoxybutane

b. 1−iodo−2−methylcyclopentane→ 1−methylcyclopentanol

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