Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 15, Problem 46P
Interpretation Introduction
(a)
Interpretation:
The structural formula for 1-phenyl-2-amino-1-propanol should be drawn.
Concept introduction:
The spatial arrangement of atom within a compound that are joined together is identified with the help of structural formula.
Interpretation Introduction
(b)
Interpretation:
The numbers of stereocenters present in the given molecule and the number of stereoisomers is possible for it should be determined.
Concept introduction:
The spatial arrangement of atom within a compound that is joined together is identified with the help of structural formula.
In chiral organic molecules, the tetrahedral carbon atom is bound to four different groups. Such a carbon is known as stereocenter.
For a molecule with n number of stereocenters, the maximum number of possible stereoisomers is 2n.
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Chapter 15 Solutions
Introduction To General, Organic, And Biochemistry
Ch. 15.1 - Prob. 15.1QCCh. 15.2 - Problem 16-2 Write a structural formula for each...Ch. 15.2 - Prob. 15.3QCCh. 15.3 - Problem 16-4 Select the stronger base from each...Ch. 15.3 - Prob. 15.5QCCh. 15 - 16-6 Answer true or false. te/7-Butylamine is a 3°...Ch. 15 - Prob. 2PCh. 15 - Prob. 3PCh. 15 - 16-9 In what way are pyridine and pyrimidine...Ch. 15 - Prob. 5P
Ch. 15 - Prob. 6PCh. 15 - Prob. 7PCh. 15 - 16-13 Classify each amino group as primary,...Ch. 15 - Prob. 9PCh. 15 - 16-15 There are eight primary amines with the...Ch. 15 - Prob. 11PCh. 15 - 16-17 Propylamine (bp 48°C), ethylmethylamine (bp...Ch. 15 - 16-18 Account for the fact that 1-butanamine (bp...Ch. 15 - 16-19 2-Me thy 1 propane (bp -12°C), 2-propanol...Ch. 15 - Prob. 15PCh. 15 - Prob. 16PCh. 15 - Prob. 17PCh. 15 - Prob. 18PCh. 15 - Prob. 19PCh. 15 - Prob. 20PCh. 15 - 16-26 The p/fb of amphetamine is approximately 3.2...Ch. 15 - 16-27 Guanidine, p/Ca 13.6, is a very strong base,...Ch. 15 - 16-28 Following is the structural formula of...Ch. 15 - Prob. 24PCh. 15 - Prob. 25PCh. 15 - Prob. 26PCh. 15 - 16*32 Many tumors of the breast are correlated...Ch. 15 - Prob. 28PCh. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - (Chemical Connections 15B ) Identify all...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Prob. 35PCh. 15 - Prob. 36PCh. 15 - (Chemical Connections 15D ) Suppose you saw this...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - 16-46 Arrange these three compounds in order of...Ch. 15 - Prob. 42PCh. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - Prob. 47PCh. 15 - Prob. 48PCh. 15 - 16-54 Several poisonous plants, including Atropa...Ch. 15 - Prob. 50PCh. 15 - Prob. 51PCh. 15 - Prob. 52PCh. 15 - 16-58 Following is a structural formula of...Ch. 15 - Prob. 54P
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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_forward18-18 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_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
- 16-19 2-Me thy 1 propane (bp -12°C), 2-propanol (bp 82°C), and 2-propanamine (bp 32°C) all have approximately the same molecular weight, yet their boiling points are quite different. Explain the reason for these differences.arrow_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_forward17-67 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_forward
- 16-18 Account for the fact that 1-butanamine (bp 78°C) has a lower boiling point than 1-butanol (bp 117°C)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_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
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