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 16, Problem 16.28P
16-28 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.
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Chapter 16 Solutions
Introduction to General, Organic and Biochemistry
Ch. 16.1 - Problem 16-1 How many hydrogen atoms does...Ch. 16.2 - Problem 16-2 Write a structural formula for each...Ch. 16.2 - Prob. 16.3PCh. 16.4 - Problem 16-4 Select the stronger base from each...Ch. 16.5 - Prob. 16.5PCh. 16 - 16-6 Answer true or false. te/7-Butylamine is a 3°...Ch. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - 16-9 In what way are pyridine and pyrimidine...Ch. 16 - Prob. 16.10P
Ch. 16 - Prob. 16.11PCh. 16 - Prob. 16.12PCh. 16 - 16-13 Classify each amino group as primary,...Ch. 16 - Prob. 16.14PCh. 16 - 16-15 There are eight primary amines with the...Ch. 16 - Prob. 16.16PCh. 16 - 16-17 Propylamine (bp 48°C), ethylmethylamine (bp...Ch. 16 - 16-18 Account for the fact that 1-butanamine (bp...Ch. 16 - 16-19 2-Me thy 1 propane (bp -12°C), 2-propanol...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - 16-26 The p/fb of amphetamine is approximately 3.2...Ch. 16 - 16-27 Guanidine, p/Ca 13.6, is a very strong base,...Ch. 16 - 16-28 Following is the structural formula of...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - 16*32 Many tumors of the breast are correlated...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16-35 (Chemical Connections 16B ) What is an...Ch. 16 - Prob. 16.36PCh. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - Prob. 16.41PCh. 16 - Prob. 16.42PCh. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - Prob. 16.45PCh. 16 - 16-46 Arrange these three compounds in order of...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16-54 Several poisonous plants, including Atropa...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - Prob. 16.57PCh. 16 - 16-58 Following is a structural formula of...Ch. 16 - Prob. 16.59P
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- 16-54 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_forward16-17 Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3HgN. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.arrow_forward16-58 Following is a structural formula of desosamine, a sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago. ch3 T Desosamine Name all the functional groups in desosamine. (Chapter 10) How many stereocenters are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it? Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial. (d > Which of the alternative chair conformations for desosamine is more stable?arrow_forward
- 16-13 Classify each amino group as primary, secondary, or tertiary and as aliphatic or aromatic. Serotonin (a neurotransmitter) Diphenhydramine (the hydrochloride salt is the antihistamine Benadryl) Lysine (an amino acid)arrow_forward17-28 Show how acetaldehyde can form hydrogen bonds with water.arrow_forward13-33 Following is the structural formula of albuterol (Proventil), one of the most widely used inhalation bronchodilators. HO Z Name the functional groups present in albuterol Draw a structural formula for the product formed when albuterol is treated with one equivalent of aqueous sodium hydroxide. Draw a structural formula for the product formed when albuterol is treated with one equivalent of hydrochloric acid.arrow_forward
- 17-67 Draw structural formulas for these compounds. (a) 1-Chloro-2-propanone (b) 3-Hydroxybutanal (c) 4-Hydroxy-4-methyl-2-pentanone (d) 3-Methyl-3-phenylbutanal (e) 1,3-Cyclohexanedione (f) 5-Hydroxyhexanalarrow_forward17-54 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_forward17-72 The following molecule is an enediol; each carbon of the double bond carries an —OH group. Draw structural formulas for the hydroxyketone and the a-hydroxyaldehyde with which this enediol is in equilibrium.arrow_forward
- 18-18 Propanoic acid and methyl acetate are constitutional isomers, and both are liquids at room temperature. One of these compounds has a boiling point of 141°C; the other has a boiling point of 57°C. Which compound has which boiling point? Explain.arrow_forward17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C) have about the same molecular weight, yet their boiling points differ by almost 50°C. Explain this fact.arrow_forward18-19 The following compounds have approximately the same molecular weight: hexanoic acid, heptanal, and 1-heptanol. Arrange them in order of increasing boiling point.arrow_forward
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