10. Addition Reactions

Suggest an alkene that could be used to make each of the following halohydrins.

(a)

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(a)

Provide arrow-pushing mechanisms for Assessments 9.10(b) and 9.10(c) that rationalize the regioselective and stereospecific formation of each halohydrin.

(b)

(c)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(h)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O

(k)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(k)

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.

(c)

When alkenes react with bromine in water, a halohydrin is produced. When water is replaced with methanol in this reaction, a different product is produced. Suggest a mechanism for the formation of this product.

Explain why water attacks the carbon of the bromonium ion as opposed to the bromonium ion itself in the second step of halohydrin formation.

Suggest an alkene that could be used to make each of the following halohydrins.

(c)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH.

(e)

Predict the product of the following haloalkane syntheses.

(e)