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 14.30P
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.
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Phenols are aromatic rings with an alcohol functional group attached directly to the ring. These compounds have unique acidity and solubility for alcohol groups. Predict the solubility of this phenol in water.
Draw the product of the reaction between a ketone and an alcohol. Include all hydrogen atoms in the product.
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How would you classify the product of the reaction? Note that a hemiacetal formed from a ketone is also called a
hemiketal; an acetal formed from a ketone is also called a ketal.
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The product is a ketone.
The product is a hemiketal.
The product is an alcohol.
The product is a ketal.
For the ketone displayed below, choose the name that follows IUPAC
guidelines.
CH,—CH,−C−CH,—CH,
(Hint: For this molecule, pay attention to the longest continuous carbon chain, which has 8
carbons. You may first want to redraw the formula to have the longest carbon chain on a
horizontal plane to facilitate naming.)
O 6-ethyl-6-methyl-3-hexanone
O 6-methyl-3-octanone
6-ethyl-3-heptanone
CH₂ CH3
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CH-CH3
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2-ethyl-5-heptanone
6,7-dimethyl-3-heptanone
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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- 14-28 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_forward14-15 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.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_forward
- 14-33 Write equations for the reaction of 1-butanol, a primary alcohol, with these reagents. H2SO4, heat K2Cr2O7, H2SO4arrow_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_forward10-45 Draw structural formulas for the eight aldehydes with the molecular formula CgHi2O.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_forward14-39 Name two important alcohols derived from ethylene and give two important uses of each.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
- 14-55 (Chemical Connections 140 The legal definition of being under the influence of alcohol is based on blood alcohol content. What is the relationship between breath alcohol content and blood alcohol content?arrow_forward14-36 Show how to convert cyclohexanol to these compounds. Cyclohexene Cyclohexane Cyclohexanone Bromocyclohexanearrow_forward17-73 Alcohols can be prepared by the acid-catalyzed hydration of alkenes (Section 12-6B) and by the reduction of aldehydes and ketones (Section 17-4B). Show how you might prepare each of the following alcohols by (1) acid-catalyzed hydration of an alkene and (2) reduction of an aldehyde or a ketone. (a) Ethanol (b) Cyclohexanol (c) 2-Propanol (d) 1-Phenylethanolarrow_forward
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