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 17, Problem 17.15P
17-15 Draw structural formulas for the four
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Terpineol has 5 isomers. Write their structures and describe why chemically (optically) they receive those names. Number the carbons for a better description.
17-24 In each pair of compounds, select the one with the
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(a) Acetaldehyde or ethanol
(b) Acetone or 3-pentanone
(c) Butanal or butane
(d) Butanone or 2-butanol
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Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
Ch. 17.2 - Problem 17-1 Wrtie the IUPAC name for each...Ch. 17.2 - Prob. 17.2PCh. 17.2 - Prob. 17.3PCh. 17.4 - Prob. 17.4PCh. 17.4 - Prob. 17.5PCh. 17.4 - Problem 17-6 Show the reaction of benzaldehyde...Ch. 17.4 - Problem 17-7 Identify all hemiacetals and acetals...Ch. 17.5 - Prob. 17.8PCh. 17 - 17-9 Answer true or false. (a) The one aldehyde...Ch. 17 - Prob. 17.10P
Ch. 17 - 17-11 What is the difference in structure between...Ch. 17 - 17-12 Is it possible for the carbon atom of a...Ch. 17 - 17-13 Which compounds contain carbonyl groups?Ch. 17 - 17-14 Following are structural formulas for two...Ch. 17 - 17-15 Draw structural formulas for the four...Ch. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - 17-18 Draw structural formulas for these ketones....Ch. 17 - 17-19 Write the JUPAC names for these compounds.Ch. 17 - Prob. 17.20PCh. 17 - 17-2 1 Explain why each name is incorrect. Write...Ch. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - 17-24 In each pair of compounds, select the one...Ch. 17 - Prob. 17.25PCh. 17 - 17-26 Account for the fact that acetone has a...Ch. 17 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 17 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 17 - 17-29 Why can’t two molecules of acetone form a...Ch. 17 - 17-30 Answer true or false. (a) The reduction of...Ch. 17 - 17-3 1 Draw a structural formula for the principal...Ch. 17 - Prob. 17.32PCh. 17 - 17-33 What simple chemical test could you use to...Ch. 17 - 17-34 Explain why liquid aldehydes are often...Ch. 17 - 17-35 Suppose that you take a bottle of...Ch. 17 - 17-36 Explain why the reduction of an aldehyde...Ch. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - 17-47 What is the characteristic structural...Ch. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - 17-54 Following is the structure of...Ch. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - 17-60 1-Propanol can be prepared by the reduction...Ch. 17 - Prob. 17.61PCh. 17 - 17-62 Show how to bring about these conversions....Ch. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - 17-67 Draw structural formulas for these...Ch. 17 - Prob. 17.68PCh. 17 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 17 - 17-70 What simple chemical test could you use to...Ch. 17 - Prob. 17.71PCh. 17 - 17-72 The following molecule is an enediol; each...Ch. 17 - 17-73 Alcohols can be prepared by the...Ch. 17 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - 17-78 Complete the following equation for these...Ch. 17 - 17-79 Write an equation for each conversion. (a)...
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- 17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes. (a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility. (b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it? (c) Are there any aromatic components in this molecule? (d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter. (e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal. (f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.arrow_forward18-6 Name and draw structural formulas for the four carboxylic acids with the molecular formula C5H10O2. Which of these carboxylic acids are chiral?arrow_forward16-54 Several poisonous plants, including Atropa belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination. Classify the amino group in atropine as primary, secondary, or tertiary. Locate all stereocenters in atropine. Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water). Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).arrow_forward
- 17-74 Glucose, C6H12O6, contains an aldehyde group but exists predominantly in the form of the cyclic hemiacetal shown here. We will discuss this cyclic form of glucose in Chapter 20. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. (a) Which carbon in glucose provides the —OH group and which provides the —CHO group? (b) Draw the alternative chair confirmations of D-glucose and state which of the two is the more stable.arrow_forward17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward17-12 Is it possible for the carbon atom of a carbonyl group to be a stereocenter? Explain.arrow_forward
- 17-73 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_forward17-70 What simple chemical test could you use to distinguish between the members of each pair of com pounds? Tell what you would do, what you would expect to observe, and how you would interpret your experimental observation. (a) Benzaldehyde and cyclohexanone (b) Acetaldehyde and acetonearrow_forward16-28 Following is the structural formula of metformin, the hydrochloride salt of which is marketed as the antidiabetic medication Glucophage. Metformin was introduced into clinical practice in the United States in 1995 for the treatment of type 2 diabetes. More than 25 million prescriptions for this drug were written in 2000, making it the most commonly prescribed brand-name diabetes medication in the nation. NH NH H3(\ 3 N N Nh2ch3 h Metformin Complete the Lewis structure for metformin, showing all valence electrons. Which nitrogen is the most likely site of protonation? Draw the structural formula of Glucophage.arrow_forward
- 13-27 Define autoxidation.arrow_forward17-18 Draw structural formulas for these ketones. (a) Ethyl isopropyl ketone (b) 2-Chiorocyclohexanone (c) 2,4-Dimethyl-3-pentanone (d) Diisopropyl ketone (e) Acetone (f) 2,5-Dimethylcyclohexanonearrow_forward13-39 (Chemical Connections 13B) What is a carcinogen What kind of carcinogen is found in cigarette smoke?arrow_forward
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