10. Addition Reactions

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.

(d)

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

(f)

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.

(e)

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

(d)

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(j)

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

c. maleic acid to (±)-tartaric acid.

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.

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)

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

(k)

Show how you would accomplish the following conversions.

a. cis-hex-3-ene to meso-hexane-3,4-diol

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)

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)

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

(a)

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)