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Chapter 6: Problem 140

An unknown compound A rapidly decolorized a solution of bromine in carbon tetrachloride. When A was subjected to ozonolysis, the products were butanone and propanal. What might be the structure of \(\mathrm{A}\) ?

Short Answer

Expert verified
The probable structure of compound A is \(CH_3CH_2CH=CHCH_3\), as it decolorizes a bromine solution and forms butanone and propanal after ozonolysis.

Step by step solution

01

Identify the products of ozonolysis

According to the given information, butanone and propanal are the products of ozonolysis. Their molecular structures are shown below: - Butanone: \(CH_3CH_2COCH_3\) - Propanal: \(CH_3CH_2CHO\)
02

Reconnect the products to form the original molecule

As ozonolysis cleaves the carbon-carbon double bond, we need to combine the two products in such a way that we can form the structure of compound A with a carbon-carbon double bond. Imagine that we took a carbon from the carbonyl group of butanone and a carbon from the aldehyde group of propanal, and reconnect them with a double bond to form the original molecule. The structure of compound A will be: - Compound A: \(CH_3CH_2CH=CHCH_3\)
03

Verify the structure using information about bromine decolorization

To confirm our proposed structure, it should decolorize bromine in carbon tetrachloride (i.e., participate in the addition reaction with bromine). Since compound A contains a carbon-carbon double bond, it will react with bromine to form 1,2-dibromoheptane. Thus, the probable structure of compound A is \(CH_3CH_2CH=CHCH_3\).

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Most popular questions from this chapter

Describe dehalogenation of vicinal dihalides to obtain an alkene.

Treatment of \(\mathrm{C}_{7} \mathrm{H}_{15} \mathrm{Br}\) with strong base gave an alkene mixture that was shown by careful gas chromatographic analysis and separation to consist of three alkenes, \(\mathrm{C}_{7} \mathrm{H}_{14}\), A, B, and C. Catalytic hydrogenation of each alkene gave 2-methythexane. Reaction of A with \(\mathrm{B}_{2} \mathrm{H}_{6}\) followed by \(\mathrm{H}_{2} \mathrm{O}_{2}\) and \(\mathrm{OH}^{-}\) gave mostly an alcohol, D. Similar reaction of \(\mathrm{B}\) or C gave approximately equal amounts of \(\mathrm{D}\) and an isomeric alcohol \(\mathrm{E}\). What structural assignments can be made for \(\mathrm{A}\) to \(E\) on the basis of these observations? What structural element is left undetermined by these data alone?

Consider the feasibility of a free-radical chain mechanism for hydrogenation of ethylene in the vapor state at \(25^{\circ}\) by the following propagation steps: $$ \begin{aligned} &\mathrm{CH}_{3}-\mathrm{CH}_{2}+\mathrm{H}_{2} \rightarrow \mathrm{CH}_{3}-\mathrm{CH}_{3}+\mathrm{H} \\ &\mathrm{CH}_{2}=\mathrm{CH}_{2}+\mathrm{H} \cdot \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \end{aligned} $$

Describe dehydration of alcohols to obtain an alkene.

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