2. Consider the oxidation cyclodod ion of eyelododecanol (1) to cyelododecanone

Question

2. Consider the oxidation cyclodod ion of eyelododecanol (1) to cyelododecanone (2) (E4 16.20) to answer the following (16 20) Cyclododecsaone A. B. C. What was the purpose of adding acetic acid to the reaction mixture in Eq 16.20 is the oxidation number of the carbon atom bearing the a lcohol functional group, in is the oxidation number of the carbon atom bearing the ketone functional group in (2) D. What is the oxidizing agent in Eq 16.20, and to what is it reduced during the course of the reaction? E. Write the molecular formulas of two different reagents that can oxidize (1) into (2), other than hypochlorite salts F. Draw the structural formula of a side-product that might be formed by the a-halogenation of (2) 3. Which reagent would you use to convert c yclododecanone (2) to cyclododecanol (1)? 4. What was the purpose of testing the reaction mixture in Eq 16.20 with starchviodide paper? Write the balanced chemical equation that transforms iodide ion into iodine in this test

Explanation / Answer

a)Carbon bearing functional group OH

the functional group oxidation state = -2 + 1=1

hence, the overall oxidation state = 0

Let oxidation state of C be x

x-1=0, x=+1

oxidation state of carbon bearing OH functional group =+1

b) carbon bearing functional group carbonyl C=O

let the oxidation state of Carbon be x

overall oxidation state = 0

oxidation state of O =-2

hence, x + (-2) , x-2 =0, x= +2

oxidation of carbon bearing functional group +2

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