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Chapter 14: Problem 29

The following is the mass spectrum of compound \(\mathrm{C}, \mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Compound \(\mathrm{C}\) is infinitely soluble in water, undergoes reaction with sodium metal with the evolution of a gas, and undergoes reaction with thionyl chloride to give a water-insoluble chloroalkane.

Short Answer

Expert verified
Answer: Compound C could be either 1-propanol or 2-propanol. Both of these structures satisfy the given conditions and share the molecular formula C3H8O.

Step by step solution

01

Identify the functional group in the compound

Based on the molecular formula (C3H8O), we can determine that the compound must have one oxygen atom. Given that it is infinitely soluble in water, we can eliminate ether as a possible functional group, as ethers have limited solubility in water. The remaining possibilities are alcohol and aldehyde. However, it reacts with sodium metal, and alcohols react with sodium to produce hydrogen gas, which is one of the given properties. Therefore, the functional group in compound C must be an alcohol.
02

Identify the position of the hydroxyl group

Since the molecular formula of the compound is C3H8O and it is an alcohol, it can have two different structures: 1-propanol (CH3-CH2-CH2-OH) or 2-propanol (CH3-CH(OH)-CH3). We are given that it reacts with thionyl chloride (SOCl2) to give a water-insoluble chloroalkane. Only primary and secondary alcohols react with thionyl chloride to replace the hydroxyl group with a chlorine atom. This means that the alcohol in compound C must be either 1-propanol or 2-propanol because they both have primary and secondary hydroxyl groups.
03

Determine the structure of compound C

We have narrowed down the possibilities for compound C to 1-propanol and 2-propanol. Both of these structures have the molecular formula C3H8O and satisfy the given conditions, so we conclude that compound C can be either 1-propanol or 2-propanol.

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Most popular questions from this chapter

Show how the compounds with the molecular formulas \(\mathrm{C}_{6} \mathrm{H}_{9} \mathrm{~N}\) and \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{NO}\) can be distinguished by the \(m / z\) ratio of their molecular ions in high- resolution mass spectrometry.

The low-resolution mass spectrum of 2-pentanol shows 15 peaks. Account for the formation of the peaks at \(m / z 73,70,55,45,43\), and, 41 .

Following is the mass spectrum of 1,2 -dichloroethane. (a) Account for the appearance of an \(\mathrm{M}+2\) peak with approximately two-thirds the intensity of the molecular ion peak. (b) Predict the intensity of the \(M+4\) peak. (c) Propose structural formulas for the cations of \(m / z 64,63,62,51,49,27\), and 26 .

Write molecular formulas for the five possible molecular ions of \(m / z 88\) containing the elements \(\mathrm{C}, \mathrm{H}, \mathrm{N}\), and \(\mathrm{O}\).

A characteristic peak in the mass spectrum of most aldehydes occurs at \(m / z 29\). What cation does this peak represent? (No, it is not an ethyl cation, \(\mathrm{CH}_{3} \mathrm{CH}_{2}{ }^{+}\).)
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