10. Addition Reactions

Cyclooctene is one of the smaller rings that can form a trans alkene. Would you expect cis-cyclooctene or trans-cyclooctene to react more quickly in an acid-catalyzed hydration reaction?

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(d)

What is the product of the reaction of maleate and H₂O when H₂SO4 is used as a catalyst instead of fumarase?

The pK_a values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.

b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.

Suggest an arrow-pushing mechanism that accounts for the formation of the following products.

(a)

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(b) two different alkenes

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(g)

How can the following compounds be prepared from 3,3-dimethyl-1-butene?

b. 3,3-dimethyl-2-butanol

Propose a mechanism for the following reaction:

Which compound is hydrated more rapidly?

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄ , H₂O

(a)

Suggest a mechanism for the synthesis of farnesol beginning with IPP and DPP.

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H₂O. If there is no reaction, write 'no reaction.'

(a)

Using any alkene and any other reagents, how would you prepare the following compounds?

e.