10. Addition Reactions

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH

(k)

Show a mechanism for the formation of one isomer in each of the reactions in Assessment 9.1.

(c)

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.

(g)

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

b. cyclohexylmethanol

Suggest a reagent to carry out each of the following conversions to an alcohol.

(d)

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: (i) 1. BH₃ 2. NaOH, H₂O₂. If there is no reaction, write 'no reaction.'

(a)

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Identify A through O:

Hydroboration, an electrophilic addition reaction like those studied in Section 21.4, only gives 1,2-addition to buta-1,3-diene, regardless of temperature. Why?

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(c)

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

(c)

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(b)

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(a)

Predict the products you would get when the following alkenes undergo (i) hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂ or (ii) oxymercuration–reduction [1. Hg(OAc)₂, H₂O 2. NaBH₄].

(a)