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Magazine Chapter 9: Q34 E (page 286)
Propose structures for hydrocarbons that give the following products
on oxidative cleavage by KMnO4 or O3 :
Short Answer
Step by step solution
Oxidative cleavage
Alkynes can be cleaved by oxidizing agents like KMnO4 or ozone. Triple bonds comprise less reactivity than double bonds and produce low yields.
The reactant that gives the products in (a)
(a)The products, heptanoic acid and carbon dioxide are produced when oct-1-yne is treated with KMnO4 and H3O+. So the hydrocarbon is oct-1-yne. The reaction can be given as:
Hydrocarbon that produces the products in (a)
The reactant that gives the products in (b)
(b)The products benzoic acid and acetic acid are produced when prop-1-yn-1-ylbenzene reacts with KMnO4 and H3O+. So, the hydrocarbon is prop-1-yn-1-ylbenzene. The reaction can be given as:
Hydrocarbon that produces the products in (b)
The reactant that gives the products in (c)
(c)The product decane-1,2-dioic acid is obtained when cyclodecyne undergoes cleavage by KMnO4 and H3O+. So the hydrocarbon is cyclodecyne. The reaction can be given as:
Hydrocarbon that produces the products in (c)
The reactant that gives the products in (d)
(d)The products acetaldehyde, 4-oxopentanoic acid and carbon dioxide are obtained when 5-methylhept-5-en-1-yne undergoes cleavage in the presence of KMnO4 and H3O+ . So the hydrocarbon is 5-methylhept-5-en-1-yne. The reaction can be given as:
Hydrocarbon that produces the products in (d)
The reactant that gives the products in (e)
(e)The hydrocarbon that produces the products 2,7-dioxoheptanoic acid and carbon dioxide is 1-ethynylcyclohex-1-ene. The reaction can be given as:
Hydrocarbon that produces the products in (e)
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