Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 14, Problem 14.15P
14-15 Both alcohols and phenols contain an —OH group. What structural feature distinguishes these two classes of compounds? Illustrate your answer by drawing the structural formulas of a phenol with six carbon atoms and an alcohol with six carbon atoms.
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Chapter 14 Solutions
Introduction to General, Organic and Biochemistry
Ch. 14.1 - Prob. 14.1PCh. 14.1 - Prob. 14.2PCh. 14.2 - Problem 14-3 Draw structural formulas for the...Ch. 14.2 - Prob. 14.4PCh. 14.2 - Prob. 14.5PCh. 14.3 - Problem 14-6 Write the common name for each ether.Ch. 14.4 - Prob. 14.7PCh. 14 - 14-8 Answer true or false. The functional group of...Ch. 14 - 14-9 What is the difference in structure between a...Ch. 14 - 14-10 Which of the following are secondary...
Ch. 14 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 14 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - 14-15 Both alcohols and phenols contain an —OH...Ch. 14 - Prob. 14.16PCh. 14 - 14-17 Explain in terms of noncovalent interactions...Ch. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - 14-20 Show hydrogen bonding between methanol and...Ch. 14 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 14 - 14-22 Arrange these compounds in order of...Ch. 14 - 14-23 Arrange these compounds in order of...Ch. 14 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 14 - 14-25 Explain why glycerol is much thicker (more...Ch. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - 14-28 Give the structural formula of an alkene or...Ch. 14 - Prob. 14.29PCh. 14 - 14-30 Show how to distinguish between cyclohexanol...Ch. 14 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 14 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 14 - 14-33 Write equations for the reaction of...Ch. 14 - 14-34 Write equations for the reaction of...Ch. 14 - 14-35 Write equations for the reaction of each of...Ch. 14 - 14-36 Show how to convert cyclohexanol to these...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - 14-39 Name two important alcohols derived from...Ch. 14 - 14-40 Name two important alcohols derived from...Ch. 14 - Prob. 14.41PCh. 14 - 14-42 Write the common name for each ether. ch3...Ch. 14 - Prob. 14.43PCh. 14 - 14-44 Answer true or false. (a) The functional...Ch. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - 14-47 Following are structural formulas for...Ch. 14 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 14 - 14-49 Answer true or false. Today, the major...Ch. 14 - Prob. 14.50PCh. 14 - 14-51 (Chemical Connections 14B) When was...Ch. 14 - 14-52 (Chemical Connections 14B) What was Alfred...Ch. 14 - Prob. 14.53PCh. 14 - 14-54 (Chemical Connections 14C) What is the color...Ch. 14 - 14-55 (Chemical Connections 140 The legal...Ch. 14 - 14-56 (Chemical Connections 14D) What does it mean...Ch. 14 - 14-57 (Chemical Connections 14E) What are the...Ch. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - 14-60 Write a balanced equation for the complete...Ch. 14 - 14-61 Knowing what you do about electronegativity,...Ch. 14 - 14-62 Draw structural formulas and write IUPAC...Ch. 14 - Prob. 14.63PCh. 14 - 14-64 Explain why the boiling point of ethylene...Ch. 14 - Prob. 14.65PCh. 14 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 14 - 14-67 Of the three compounds given in Problem...Ch. 14 - Prob. 14.68PCh. 14 - 14-69 Show how to prepare each compound from...Ch. 14 - 14-70 Show how to prepare each compound from...Ch. 14 - 14-71 The mechanism of the acid-catalyzed...Ch. 14 - Prob. 14.72PCh. 14 - 14-73 Lipoic acid is a growth factor for many...Ch. 14 - 14-74 Following is a structural formula for the...Ch. 14 - Prob. 14.75PCh. 14 - Prob. 14.76PCh. 14 - Prob. 14.77PCh. 14 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 14 - Prob. 14.79P
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- 14-30 Show how to distinguish between cyclohexanol and cyclohexene by a simple chemical test. Tell what you would do, what you would expect to see, and how you would interpret your observation.arrow_forward14-66 1,4-Butanediol, hexane, and 1-pentanol have similar molecular weights. Their boiling points, arranged from lowest to highest, are 69°C, 138°C, and 230°C. Which compound has which boiling point?arrow_forward14-28 Give the structural formula of an alkene or alkenes from which each alcohol can be prepared. 2-Butanol 1-Methylcyclohexanol 3-Hexanol 2-Methyl-2-pentanol Cyclopentanolarrow_forward
- 14-47 Following are structural formulas for 1-butanol and 1-butanethiol. One of these compounds has a boiling point of 98°C and the other has a boiling point of 117°C. Which compound has which boiling point? ch3ch2ch2ch,oh ch3ch2ch2ch2sh 1-Butanol 1-Butanethiolarrow_forward14-33 Write equations for the reaction of 1-butanol, a primary alcohol, with these reagents. H2SO4, heat K2Cr2O7, H2SO4arrow_forward14-74 Following is a structural formula for the amino acid cysteine: O II HS—CH — CH—C —OH I nh2 Name the three functional groups in cysteine. In the human body, cysteine is oxidized to cystine, a disulfide. Draw a structural formula for cystine.arrow_forward
- 14-49 Answer true or false. Today, the major carbon sources for the synthesis of methanol are coal and methane (natural gas), both nonrenewable resources. Today the major carbon sources for the synthesis of ethanol are petroleum and natural gas, both nonrenewable resources. Intermolecular acid-catalyzed dehydration of ethanol gives diethyl ether. Conversion of ethylene to ethylene glycol involves oxidation to ethylene oxide, followed by acid-catalyzed hydration (addition of water, to ethylene oxide. Ethylene glycol is soluble in water in all proportions. A major use of ethylene glycol is as automobile antifreeze.arrow_forward13-19 Suppose you have unlabeled bottles of benzene and cyclohexene. What chemical reaction could you use to tell which bottle contains which chemical? Explain what you would do, what you would expect to see, and how you would explain your observations. Write an equation for a positive test.arrow_forward13-25 Answer true or false. (a) Phenols and alcohols have in common the presence of an —OH group. Phenols are weak acids and react with strong bases to give water-soluble salts. The pK„ of phenol is smaller than that of acetic acid. Autoxidation converts an R—H group to an R—OH group. A carbon radical has only seven electrons in the valence shell of one of its carbons, and this carbon bears a positive charge. (f, A characteristic of a chain initiation step is conversion of a nonradical to a radical. Autoxidation is a radical-chain reaction. A characteristic of the chain propagation step is reaction of a radical and a molecule to form a new radical and a new molecule. Vitamin E and other natural antioxidants function by interrupting the cycle of chain propagation steps that occurs in autoxidation.arrow_forward
- 13-20 Three products with the molecular formula CgH^BrCl form when bromobenzene is treated with chlorine, Cl2, in the presence of FeCl3 as a catalyst. Name and draw a structural formula for each product.arrow_forward14-9 What is the difference in structure between a primary, a secondary, and a tertiary alcohol?arrow_forward14-17 Explain in terms of noncovalent interactions why the low-molecular-weight alcohols are soluble in water but the low-molecular-weight alkanes and alkynes are not.arrow_forward
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