10. Addition Reactions

Predict the major products of the following reactions.

a. propene + BH₃⋅THF

b. the product from part (a) + H₂O₂/OH⁻

Show how you would make the following compounds from a suitable cyclic alkene.

(e)

Show how you would accomplish the following transformations.

(b)

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.

(d)

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

(b)

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

(g)

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: