Chapter Questions
Draw general formulas for an alcohol and phenol, showing the functional group.
Draw a general formula for an ether, emphasizing the functional group.
Assign IUPAC names to the following alcohols:
Several important alcohols are well known by common names. Give a common name for each of the following:
Give each of the structures in Exercise 13.5 an IUPAC name.
Draw structural formulas for each of the following:a. 2-methyl-1-butanolb. 2-bromo-3-methyl-3-pentanolc. 1-methylcyclopentanol
Draw structural formulas for each of the following:a. 2-methyl-2-pentanolb. 1,3-butanediolc. 1-ethylcyclopentanol
Each of the following alcohols is named incorrectly. Draw structural formulas, and then give the correct IUPAC name for each alcohol.a. 1,5-cyclohexanediolb. 3-ethyl-2-butanolc. 2-ethyl-1-propanold. 3,4-pentanediol
Each of the following alcohols is named incorrectly. Draw structural formulas, and then give the correct IUPAC name for each alcohol.a. 2,4-butanediolb. 2-propyl-3-butanolc. 3-methyl-3-butanold. 1,4-cyclopentanediol
Give IUPAC names for all the unbranched (normal) $\mathrm{C}_7$ carbon chain alcohols that only have one -OH group. There are four isomers.
Give IUPAC names for all the unbranched (normal) $C_8$ car bon chain alcohols that only have one -OH group. There are four isomers.
Name each of the following as a derivative of phenol:
Draw structural formulas for each of the following:a. m-methylphenolb. 2,3-dichlorophenol
Draw structural formulas for each of the following:a. p-chlorophenolb. 2,5-diisopropylphenol
What is the difference between a primary, secondary, and tertiary alcohol?
Classify the following alcohols as primary, secondary, or tertiary:
Draw structural formulas for the eight aliphatic alcohols with the molecular formula $\mathrm{C}_5 \mathrm{H}_{12} \mathrm{O}$. Name each compound using the IUPAC system and classify it as a primary, secondary, or tertiary alcohol.
Draw structural formulas for the four aliphatic alcohols with the molecular formula $\mathrm{C}_4 \mathrm{H}_{10} \mathrm{O}$. Name each compound using the IUPAC system and classify it as a primary, secondary, or tertiary alcohol.
Why are the boiling points of alcohols much higher than the boiling points of alkanes with similar molecular weights?
Arrange the compounds of each group in order of increasing boiling point.a. 1-butanol, 1-pentanol, 1-propanolb. 1,2-butanediol, 2-butanol, pentane
Arrange the compounds of each group in order of increasing boiling point.a. Ethanol, 1-propanol, methanolb. Butane, Ethylene glycol, 1-propanol
Which member of each of the following pairs would you expect to be more soluble in water? Briefly explain your choices.a. 2,3-pentanediol or 2,3,4-pentanetriolb. Hexane or 3-hexanolc. 1-butanol or 2-octanol
Which member of each of the following pairs would you expect to be more soluble in water? Briefly explain your choices.a. butane or 2-butanolb. 2-propanol or 2-pentanolc. 2-butanol or 2,3-butanediol
Draw structural formulas for the following molecules and use a dotted line to show the formation of hydrogen bonds:a. one molecule of 3-pentanol and one molecule of 1-propanolb. 2-propanol and water
Draw structural formulas for the following molecules and use a dotted line to show the formation of hydrogen bonds:a. one molecule of 1-butanol and one molecule of ethanolb. cyclohexanol and water
Determine the maximum number of hydrogen bonds that can form between a 1-propanol molecule anda. other 1-propanol moleculesb. water molecules
Determine the maximum number of hydrogen bonds that can form between a 1-butanol molecule anda. other 1-butanol moleculesb. water molecules
Explain why the use of glycerol (1,2,3-propanetriol) in lotions helps retain water and keep the skin moist.
Draw the structures of the chief product formed when the following alcohols are dehydrated to alkenes:
Draw the structures of the ethers that can be produced from the following alcohols:
Draw the structures of the two organic compounds that can be obtained by oxidizing:
$$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2-\mathrm{OH}$$
Draw the structure of the product expected when each of the following alcohols is reacted with a sulfuric acid catalyst at the temperature indicated.
Draw the structural formula of the alcohol that will make the following products through an alcohol dehydration reaction.
Identify whether a primary or secondary alcohol was oxidized to make each of the following compounds.
Draw the structures of the two organic compounds that can be obtained by oxidizing
Give the structure of an alcohol that could be used to prepare each of the following compounds:
What products would result from the following processes? Write an equation for each reaction.a. 2-Methyl-2-butanol is subjected to controlled oxidation.b. 1-Propanol is heated to $140^{\circ} \mathrm{C}$ in the presence of sulfuric acid.c. 3-Pentanol is subjected to controlled oxidation.d. 3-Pentanol is heated to $180^{\circ} \mathrm{C}$ in the presence of sulfuric acid.e. 1-Hexanol is subjected to an excess of oxidizing agent.
What products would result from the following processes? Write an equation for each reaction.a. 1-Butanol is heated to $140^{\circ} \mathrm{C}$ in the presence of sulfuric acid.b. 1-Butanol is subjected to an excess of oxidizing agent.c. 2-Pentanol is subjected to controlled oxidation.d. 2-Pentanol is heated to $180^{\circ} \mathrm{C}$ in the presence of sulfuric acid.e. 2-Methyl-2-pentanol is subjected to controlled oxidation.
Each of the following conversions requires more than one step, and some reactions studied in previous chapters may be needed. Show the reagents you would use and draw structural formulas for intermediate compounds formed in each conversion.
The three-carbon diol used in antifreeze isIt is nontoxic and is used as a moisturizing agent in foods. Oxidation of this substance within the liver produces pyruvic acid, which can be used by the body to supply energy. Give the structure of pyruvic acid.
Methanol is fairly volatile and evaporates quickly if spilled. Methanol is also absorbed quite readily through the skin. If, in the laboratory, methanol accidentally spilled on your clothing, why would it be a serious mistake to just let it evaporate?
Why is methanol such an important industrial chemical?
Suppose you are making some chocolate cordials (chocolatecoated candies with soft fruit filling). Why might you want to add a little glycerol to the filling?
Name an alcohol used in each of the following ways:a. A moistening agent in many cosmeticsb. A solvent in solutions called tincturesc. Automobile antifreezed. Rubbing alcohol
Name an alcohol used in each of the following ways:a. A flavoring in cough dropsb. Present in gasoholc. Active ingredient in alcoholic beveragesd. Industrially produced from CO and $\mathrm{H}_2$
Name a phenol associated with each of the following:a. A vitaminb. A disinfectant cleaner
Name a phenol used in each of the following ways:a. A disinfectant used for cleaning wallsb. An antiseptic found in some mouthwashesc. An antioxidant used to prevent rancidity in foods
Explain why the first of the following two compounds is a phenol, and the second is not.
Which of the molecular structures below cannot possibly exist in nature? Explain why not.
Assign a common name to each of the following ethers:
Assign the IUPAC name to each of the following ethers. Name the smaller alkyl group as the alkoxy group.
Draw structural formulas for the following:a. ethyl methyl etherb. butyl phenyl etherc. 3-ethoxypentaned. dipropyl ethere. 1,3-dipropoxycyclohexane
Draw structural formulas for the following:a. methyl isopropyl etherb. phenyl propyl etherc. 2-methoxypentaned. 1,2-diethoxycyclopentanee. 2-phenoxy-2-butene
Identify each of the following molecular structures as that of a heterocyclic ring ether, a noncyclic ring ether, or a nonether.
Give the IUPAC names and draw structural formulas for the three isomeric ethers of the molecular formula $\mathrm{C}_4 \mathrm{H}_{10} \mathrm{O}$.
Give the IUPAC names and draw structural formulas for the six isomeric ethers of the molecular formula $\mathrm{C}_5 \mathrm{H}_{12} \mathrm{O}$.
What is the chief chemical property of ethers?
Why is diethyl ether hazardous to use as an anesthetic or as a solvent in the laboratory?
Arrange the following compounds in order of decreasing solubility in water. Explain the basis for your decision.
Arrange the following compounds in order of decreasing solubility in water. Explain the basis for your decisions.
Arrange the compounds in Exercise 13.74 in order of decreasing boiling point. Explain your answer.
$$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2-\mathrm{OH} \quad \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3 \quad \mathrm{CH}_3 \mathrm{CH}_2-\mathrm{O}-\mathrm{CH}_3$$
Arrange the compounds in Exercise 13.75 in order of decreasing boiling point. Explain your answer.
Draw structural formulas and use a dotted line to show hydrogen bonding between a molecule of methoxyethane and water.
Draw structural formulas and use a dotted line to show hydrogen bonding between a molecule of diethyl ether and water.
Complete the following reactions:
Lipoic acid is required by many microorganisms for proper growth. As a disulfide, it functions in the living system by catalyzing certain oxidation reactions and is reduced in the process. Write the structure of the reduction product.
Alcohols and thiols can both be oxidized in a controlled way. What are the differences in the products?
Identify the functional groups in vanillin, the active ingredient in vanilla flavoring.
Ethynlestradiol acts as an estrogen (the primary female sex hormone) and has been used in contraceptives. Identify the functional groups in this compound.
Identify the functional groups in cinnamaldehyde, present in cinnamon flavoring.
alkene + water $\stackrel{\mathrm{H}_3 \mathrm{SO}_3}{\rightleftharpoons}$ alcohol + heat
In simplistic terms, it can be thought that an equilibrium exists in the hydration-dehydration reactions above. Use LeChatelier's principle to explain why the dehydration reaction is favored at $180^{\circ} \mathrm{C}$.
Thiols have lower boiling points and are less water soluble than the corresponding alcohol (e.g., $\mathrm{CH}_3 \mathrm{CH}_2-\mathrm{OH}$ and $\mathrm{CH}_3 \mathrm{CH}_2-\mathrm{SH}$ ). Explain why.
The internal oxidation of methanol yields methanoic acid, a highly toxic compound which can result in blindness, coma, and death. Determine the oxidation numbers on the carbon atom in the following reaction.
Because of the acidity of phenol, handling the compound can result in chemical burns. Using the idea of aromaticity (the electronic structure of benzene), explain why phenol is a stronger acid than cyclohexanol.
In Section 13.6, the structure of 4-hexylresorcinol, a common component in throat lozenges, is shown. Give another name for 4-hexylresorcinol using the ending -diol.
Use general reactions to show how an alcohol $(\mathrm{R}-\mathrm{O}-\mathrm{H})$ can behave as a weak Bronsted acid when it reacts with a strong Bronsted base ( $\mathrm{X}^{-}$). Next, show how an alcohol can behave as a weak Bronsted base in the presence of a strong Bronsted acid (HA).
Many aftershaves are $50 \%$ ethanol. What do you think is the purpose of the ethanol?
A mixture of ethanol and 1-propanol is heated to $140^{\circ} \mathrm{C}$ in the presence of sulfuric acid. Careful analysis reveals that three ethers are formed. Write formulas for these three products, name each, and explain why three form, rather than a single product.
The two-carbon alcohol in some antifreeze is toxic if ingested. Reactions within the liver oxidize the diol to oxalic acid, which can form insoluble salts and damage the kidneys. Give the structure of oxalic acid.
Although ethanol is only mildly toxic to adults, it poses greater risks for fetuses. Why do you think this is the case?
The medicinal compound taxol is mentioned in Figure 13.1. What does the name indicate about its possible structure?
Norgesterone acts as a progestin (a hormone that regulates the menstrual cycle). What does the name indicate about its possible structure?
When diethyl ether is spilled on the skin, the skin takes on a dry appearance. Explain whether this effect is more likely due to a removal of water or a removal of natural skin oils.
Figure 13.12 points out that methanol is used as a fuel in racing cars. Write a balanced equation for the combustion of methanol.
Figure 13.19 focuses on the use of thiol chemistry by skunks. If thiols are more volatile than alcohols and less soluble in water, why do these properties represent an advantage to skunks?
Why do you think a dye is added to antifreeze before it is sold in stores?
Glycerol, or glycerin, is used as a moisturizer in foods such as candy and shredded coconut. What is the molecular explanation for its utility as a moisturizer?