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Chapter 11: Problem 71

Isopropyl alcohol is prepared by reacting propene \(\left(\mathrm{CH}_{3} \mathrm{CHCH}_{2}\right)\) with sulfuric acid, followed by treatment with water. (a) Show the sequence of steps leading to the product. What is the role of sulfuric acid? (b) Draw the structure of an alcohol that is an isomer of isopropyl alcohol. (c) Is isopropyl alcohol a chiral molecule? (d) What property of isopropyl alcohol makes it useful as a rubbing alcohol?

Short Answer

Expert verified
(a) Propene reacts with sulfuric acid to produce isopropyl hydrogen sulfate, which is then hydrolyzed in the presence of water to create isopropyl alcohol. Sulfuric acid catalyzes the reaction. (b) n-Propanol is an isomer of isopropyl alcohol. (c) Isopropyl alcohol is not chiral. (d) Isopropyl alcohol's ability to kill microorganisms and its rapid evaporation make it useful as a rubbing alcohol.

Step by step solution

01

Reaction sequence for isopropyl alcohol production

Propene (\(\mathrm{CH}_{3}\mathrm{CHCH}_{2}\)) reacts with sulfuric acid (\(\mathrm{H}_{2}\mathrm{SO}_{4}\)) to produce isopropyl hydrogen sulfate. This is then hydrolyzed in the presence of water to produce isopropyl alcohol. Sulfuric acid acts as a catalyst by donating a proton to the propene, which facilitates the esterification of propene. The reactions are as follows: \[\mathrm{CH}_{3}\mathrm{CH}=\mathrm{CH}_{2} + \mathrm{H}_{2}\mathrm{SO}_{4} \rightarrow \mathrm{CH}_{3}\mathrm{CH}\mathrm{OH}\mathrm{SO}_{3}\mathrm{H}\] \[\mathrm{CH}_{3}\mathrm{CH}\mathrm{OH}\mathrm{SO}_{3}\mathrm{H} + \mathrm{H}_{2}\mathrm{O} \rightarrow \mathrm{CH}_{3}\mathrm{CHOH}\mathrm{CH}_{3} + \mathrm{H}_{2}\mathrm{SO}_{4}\]
02

Structure of an isomer of isopropyl alcohol

An isomer of isopropyl alcohol is n-propanol. It has the same molecular formula (\(\mathrm{C}_{3}\mathrm{H}_{8}\mathrm{O}\)) as isopropyl alcohol but a different structure. The structure is as follows: \(\mathrm{CH}_{3}\mathrm{CHOH}\mathrm{CH}_{2}\mathrm{H}\)
03

Chirality of isopropyl alcohol

Isopropyl alcohol is not a chiral molecule. A molecule is chiral when it cannot be superimposed on its mirror image. In isopropyl alcohol, the central carbon atom is bound to two identical methyl groups, a hydrogen atom, and a hydroxyl group. Thus, the molecule has a plane of symmetry and is not chiral.
04

Utility of isopropyl alcohol as rubbing alcohol

Isopropyl alcohol is used as a rubbing alcohol because of its ability to kill many types of microorganisms. It does so by denaturing their proteins. Additionally, it is a good solvent and evaporates quickly, making it useful for cleaning purposes.

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Most popular questions from this chapter

What do "saturated" and "unsaturated" mean when applied to hydrocarbons? Give examples of a saturated hydrocarbon and an unsaturated hydrocarbon.

The structural isomers of pentane, \(\mathrm{C}_{5} \mathrm{H}_{12}\), have quite different boiling points (see Example 11.1 ). Explain the observed variation in boiling point, in terms of structure.

State at least one commercial use for each of the following compounds: (a) 2-propanol, (b) acetic acid, (c) naphthalene, (d) methanol, (e) ethanol, (f) ethylene glycol, (g) methane, (h) ethylene.

Draw all possible structural isomers for this alkane: \(\mathrm{C}_{7} \mathrm{H}_{16}\)

A compound has the empirical formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\). Upon controlled oxidation, it is converted into a compound of empirical formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O},\) which behaves as a ketone. Draw possible structures for the original compound and the final compound.
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