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Chapter 22: Problem 129

Explain why methyl alcohol is soluble in water in all proportions, while stearyl alcohol $\left[\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16} \mathrm{OH}\right]$ is a waxy solid that is not soluble in water.

Short Answer

Expert verified
Methyl alcohol is soluble in water in all proportions because both are polar molecules and can form strong hydrogen bonds. On the other hand, stearyl alcohol is insoluble in water due to its long nonpolar hydrocarbon chain which dominates the molecule, making it primarily hydrophobic. While the small polar hydroxyl group in stearyl alcohol can form hydrogen bonds with water, the unfavorable interactions between the hydrocarbon chain and water prevail, resulting in its insolubility in water.

Step by step solution

01

Analyze the structure of methyl alcohol and water.

Methyl alcohol, or methanol, has a molecular formula of \(\mathrm{CH}_{3}\mathrm{OH}\). Water has a molecular formula of \(\mathrm{H}_{2}\mathrm{O}\). Both molecules are polar, due to the electronegativity difference between oxygen and hydrogen or carbon atoms. The presence of oxygen in both molecules creates an effective dipole (separation of positive and negative charges).
02

Explain the interactions between methyl alcohol and water molecules.

Since both methyl alcohol and water are polar molecules, they form strong hydrogen bonds between the hydroxyl groups (\(\mathrm{-OH}\)) of their respective molecules. The hydrogen bond is a strong intermolecular force that helps to facilitate the dissolution of polar compounds in water. As a result, methyl alcohol is soluble in water in all proportions.
03

Analyze the structure of stearyl alcohol.

Stearyl alcohol has the molecular formula \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16}\mathrm{OH}\). The molecule consists of a long hydrocarbon chain with one hydroxyl group at the end. The long hydrocarbon chain is nonpolar due to the similar electronegativity values of the carbon and hydrogen atoms. While the hydroxyl group is polar, the majority of the molecule is dominated by the nonpolar characteristics of the hydrocarbon chain.
04

Explain the interactions between stearyl alcohol and water molecules.

Since stearyl alcohol molecule consists of a large nonpolar hydrocarbon chain and only a small polar hydroxyl group, it is primarily hydrophobic. This hydrophobicity means that the nonpolar part of stearyl alcohol does not interact favorably with polar water molecules. While the hydroxyl group can still form hydrogen bonds with water, the unfavorable interactions between the hydrocarbon chain and water dominate, making stearyl alcohol insoluble in water.
05

Summarize the findings from the analysis.

In summary, methyl alcohol is soluble in water because it is a polar compound that can form hydrogen bonds with water molecules. In contrast, stearyl alcohol is a waxy solid that is insoluble in water due to the hydrophobic nature of its long hydrocarbon chain, which dominates over the ability of its hydroxyl group to hydrogen bond with water.

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Most popular questions from this chapter

For each of the following, fill in the blank with the correct response. All of these fill-in-the-blank problems pertain to material covered in the sections on alkanes, alkenes and alkynes, aromatic hydrocarbons, and hydrocarbon derivatives. a. The first “organic” compound to be synthesized in the laboratory, rather than being isolated from nature, was , which was prepared from . b. An organic compound whose carbon–carbon bonds are all single bonds is said to be . c. The general orientation of the four pairs of electrons around the carbon atoms in alkanes is . d. Alkanes in which the carbon atoms form a single unbranched chain are said to be alkanes. e. Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit different arrangements of the between those atoms. f. The systematic names of all saturated hydrocarbons have the ending added to a root name that indicates the number of carbon atoms in the molecule. g. For a branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the continuous chain in the molecule. h. The positions of substituents along the hydrocarbon framework of a molecule are indicated by the of the carbon atom to which the substituents are attached. i. The major use of alkanes has been in reactions, as a source of heat and light. j. With very reactive agents, such as the halogen elements, alkanes undergo reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane. k. Alkenes and alkynes are characterized by their ability to undergo rapid, complete reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond. l. Unsaturated fats may be converted to saturated fats by the process of . m. Benzene is the parent member of the group of hydrocarbons called hydrocarbons. n. An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a group. o. A alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group. p. The simplest alcohol, methanol, is prepared industrially by the hydrogenation of . q. Ethanol is commonly prepared by the of certain sugars by yeast. r. Both aldehydes and ketones contain the group, but they differ in where this group occurs along the hydrocarbon chain. s. Aldehydes and ketones can be prepared by of the corresponding alcohol. t. Organic acids, which contain the group, are typically weak acids. u. The typically sweet-smelling compounds called result from the condensation reaction of an organic acid with an .

All amino acids have at least two functional groups with acidic or basic properties. In alanine, the carboxylic acid group has $K_{a}=4.5 \times 10^{-3}\( and the amino group has \)K_{b}=7.4 \times 10^{-5} .$ Three ions of alanine are possible when alanine is dissolved in water. Which of these ions would predominate in a solution with \(\left[\mathrm{H}^{+}\right]=1.0 M ?\) In a solution with \(\left[\mathrm{OH}^{-}\right]=1.0 \mathrm{M} ?\)

A common shorthand notation to draw organic structures is to use lines to represent \(\mathrm{C}-\mathrm{C}\) bonds. For example, the short- hand notation for the two structural isomers of the formula \(\mathrm{C}_{4} \mathrm{H}_{10}\) are: At the end of each zigzag line is a carbon atom. The \(\mathrm{C}-\mathrm{H}\) bonds are omitted in such shorthand notation. Use line notation to illustrate the structural isomers of \(\mathrm{C}_{6} \mathrm{H}_{14}\)

Complete the following reactions. $$ \begin{array}{l}{\text { a. } \mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}+\mathrm{CH}_{3} \mathrm{OH} \rightarrow} \\ {\text { b. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{HCOOH} \rightarrow}\end{array} $$

For each of the following, fill in the blank with the correct response(s). All of the following pertain to nucleic acids. a. The substance in the nucleus of the cell that stores and transmits genetic information is DNA, which stands for. b. The basic repeating monomer units of DNA and RNA are called . c. The pentose deoxyribose is found in DNA, whereas is found in RNA. d. The basic linkage in DNA or RNA between the sugar molecule and phosphoric acid is a phosphate linkage. e. The bases on opposite strands of DNA are said to be to each other, which means the bases fit together specifically by hydrogen bonding to one another. f. In a strand of normal DNA, the base is always found paired with the base adenine, whereas is always found paired with cytosine. g. A given segment of the DNA molecule, which contains the molecular coding for a specific protein to be synthesized, is referred to as a . h. During protein synthesis, RNA molecules attach to and transport specific amino acids to the appropriate position on the pattern provided by RNA molecules. i. The codes specified by are responsible for assembling the correct primary structure of proteins.
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