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Chapter 24: Problem 67

Isopropanol is prepared by reacting propylene \(\left(\mathrm{CH}_{3} \mathrm{CHCH}_{2}\right)\) 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 isopropanol. (c) Is isopropanol a chiral molecule? (d) What property of isopropanol makes it useful as a rubbing alcohol?

Short Answer

Expert verified
(a) Propylene reacts with sulfuric acid forming a protonated alcohol intermediate which then reacts with water to produce isopropanol. Sulfuric acid acts as a catalyst. (b) An isomer of isopropanol could be propan-1-ol. (c) Isopropanol is not a chiral molecule. (d) Isopropanol is useful as a rubbing alcohol because it can kill many types of bacteria, viruses, and fungi upon contact.

Step by step solution

01

Sequence of steps from propylene to isopropanol

Propylene \(\mathrm{CH}_{3}\mathrm{CHCH}_{2}\) is first reacted with sulfuric acid (H2SO4) which causes hydration of the double bond. The sulfuric acid acts as a catalyst in the reaction. This creates a protonated alcohol intermediate. After this step, water is added, which acts as a nucleophile attacking the carbocation and leading to the final product, isopropanol (propan-2-ol).
02

Structure of an Isomer

An isomer of isopropanol would have the same molecular formula, but a different structural formula. A possible isomer could be propan-1-ol. Here, instead of having the OH group in the middle carbon (as in isopropanol), it is attached to the terminal carbon atom.
03

Determining Chirality

Chiral molecules are molecules that cannot be superimposed on their mirror image. For a carbon atom to be a chiral center, it must have four different groups attached to it. In the case of isopropanol, the second carbon atom has two hydrogen atoms attached to it. Therefore, no carbon atom in isopropanol meets the conditions to be a chiral center, and isopropanol is not a chiral molecule.
04

Isopropanol as a rubbing alcohol

Isopropanol is used as rubbing alcohol because of its disinfectant properties. It kills many types of bacteria, viruses, and fungi upon contact. This makes it very useful for sterilization and cleaning.

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Most popular questions from this chapter

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.

Would you expect cyclobutadiene to be a stable molecule? Explain.

Suggest two chemical tests that would help you distinguish between these two compounds: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\)

Alkenes exhibit geometric isomerism because rotation about the \(\mathrm{C} \equiv \mathrm{C}\) bond is restricted. Explain.

A compound having the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) does not react with sodium metal. In the presence of light, the compound reacts with \(\mathrm{Cl}_{2}\) to form three compounds having the formula \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OCl}\). Draw a structure for the original compound that is consistent with this information.
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