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Chapter 8: Q. 52d E (page 262)

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution

d.CHC3H2C=OCH2CH2CH2CH2CO2H

Short Answer

Expert verified

KMnO4is a strong oxidising agent. In oxidative cleavage,KMnO4leads to the formation of 1,2-diol which leads to formation of the carboxylic acid andKMnO4is converted to brown MnO2.

The colour changes from purple to brown and diol lead to produce two adjacent alcoholic groups.

Step by step solution

01

Oxidation by KMnO4

KMnO4is a strong oxidising agent. In oxidative cleavage,KMnO4leads to the formation of 1,2-diol which leads to formation of the carboxylic acid andKMnO4is converted to brown MnO2.

The colour changes from purple to brown and diol lead to produce two adjacent alcoholic groups.

02

Structure of alkene while undergoing oxidation

d. Formation of CHC3H2C=OCH2CH2CH2CH2CO2H

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Most popular questions from this chapter

Question: Plexiglas, a clear plastic used to make many molded articles, is made by polymerization of methyl methacrylate. Draw a representative segment of Plexiglas.

We鈥檒l see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?

From what alkenes might the following alcohols have been prepared?

a)

Evidence that cleavage of 1,2-diols by HIO4occurs through a five membered cyclic periodate intermediate is based on kinetic data鈥攖he measurement of reaction rates. When diols A and B were prepared and the rates of their reaction withHIO4were measured, it was found that diol A cleaved approximately 1 million times faster than diol B. Make molecular models of A and B and of potential cyclic periodate intermediates, and then explain the kinetic results

Question:The addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomers isformed.
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