10. Addition Reactions

Give the products expected when the following compounds are ozonized and reduced.

(a)

(b)

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

(d)

Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.

(c)

(d)

Predict the product of the following aldehyde/ketone syntheses.

(a) <IMAGE>

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(b)

Which of the following is produced in the ozonolysis of $\mathrm{cyclohexene}$?

What is the major product of each of the following reactions?

f.

Which of the following sets of products is formed when $1-\text{butene}$ undergoes ozonolysis followed by reductive workup ($\text{Zn}/\text{AcOH}$)?

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(b)

Ozonolysis of compound z yields the products ${\mathrm{CH}}_3\mathrm{CHO}$ (acetaldehyde) and ${\mathrm{CH}}_{2}O$ (formaldehyde). What is the structure of compound z?

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

b.

Given the following reaction: $\mathrm{CH}{2}_3–\mathrm{CH}=\mathrm{CH}–\mathrm{CH}{2}_2$ treated with ozone followed by reductive workup (Zn/AcOH), what are the correct organic products (in any order)?

Which of the following sets of products is formed when $\mathrm{cyclohexene}$ undergoes ozonolysis followed by reductive workup (e.g., $\mathrm{Zn}/\mathrm{AcOH}$)?

Given the ozonolysis reaction that produces ${\mathrm{CH}}_3\mathrm{CHO}$ (acetaldehyde) and $\mathrm{HCHO}$ (formaldehyde) as products, which of the following is the correct structure of the starting alkene?