10. Addition Reactions

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO₄ 2. NaHSO₃. If there is no reaction, write 'no reaction.'

(a)

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

(b)

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

(d)

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.

(d)

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃ 

(l)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃ 

(f)

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(c)

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

(f)

Predict the major products of the following reactions, including stereochemistry.

e. trans-pent-2-ene + OsO₄/H₂O₂

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

d. a mixture of osmic acid and hydrogen peroxide

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

b. fumaric acid to meso-tartaric acid.

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(e)

Predict the major products of the following reactions.

f. 1-ethylcycloheptene + cold, dilute KMnO₄

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

a. fumaric acid to (±)-tartaric acid.

b. fumaric acid to meso-tartaric acid.