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Chapter 12: Q51E (page 354)


Draw the structure of an alkene that yields only acetone, (CH3)2C=O, on ozonolysis followed by treatment with Zn.

Short Answer

Expert verified

The organic chemical reaction in which ozone molecule is used to cleave the unsaturated bonds of alkynes, alkenes, and azo compounds is referred to as ozonolysis.

Step by step solution

01

Ozonolysis

The organic chemical reaction in which ozone molecule is used to cleave the unsaturated bonds of alkynes, alkenes, and azo compounds is referred to as ozonolysis.

02

Structure of alkene

The structure of the alkene that yields acetone is 2,3-dimethyl-2-butene acetone. This undergoes ozonolysis in the presence of Zn and cleaves the unsaturated bonds of alkene.

The reaction is as follows:

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Most popular questions from this chapter

Question: How might you use IR spectroscopy to distinguish between the following pairs of isomers?

a)CH3CH2OHandCH3OCH3b)cyclohexaneand1-hexenec)CH3CH2CO2HandHOCH2CH2CHO

Question: What functional groups might the following molecules contain?

(a) A compound with a strong absorption at 1710cm-1

(b) A compound with a strong absorption at 1540cm-1

(c) A compound with strong absorptions at 1720cm-1 and 2500 to 3100 cm-1

Question: How could you use infrared spectroscopy to distinguish between the

following pairs of isomers?

(a)HC鈮�CCH2NH2andCH3CH2C鈮�N

(b)CH3COCH3andCH3CH2CHO

The following model is a representation of ibuprofen, a common over-the-counter pain reliever. Indicate the positions of the multiple bonds, and draw a skeletal structure (gray 5 C, red 5 O, ivory 5 H).

One consequence of the base-catalyzed isomerization of unsaturated ketones described in Problem 22-55 is that 2-substituted 2-cyclopentenones can be interconverted with 5-substituted 2-cyclopentenones. Propose a mechanism for this isomerization.
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