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 12P
16-17 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.
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Propylamine (bp 48°C), ethylmethylamine (bp 37°C), and trimethylamine (bp 3°C) are constitutional isomers with the molecular formula C3H9N. Account for the fact that trimethylamine has the lowest boiling point of the three and propylamine has the highest.
The following amines have the same molecular formula (C5H13N), but their boiling points are significantly different.
Explain why.
H
`NH2
2-Methylbutan-1-amine
Boiling point = 97 °C
N-Methylbutan-2-amine
Boiling point = 84 °C
N-Ethyl-N-methylethan-1-amine
Boiling point = 65 °C
Provide the IUPAC name of (CH3)3CCH₂CH₂NHCH₂CH3.
N-methyl-3-ethyl-1-butanamine
N-ethyl-3,3-dimethyl-1-butanamine
N,N-dimethyl-1-pentanamine
octanamine
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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- 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_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_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_forward13-27 Define autoxidation.arrow_forwardArrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forward
- Compounds that contain an N-H group associate by hydrogen bonding. (a) Do you expect this association to be stronger or weaker than that of compounds containing an O-H group? (b) Based on your answer to part (a), which would you predict to have the higher boiling point, 1-butanol or 1-butanamine?arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanoneWrite the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide Why doesn’t the cis isomer yield the oxide?Write the mechanism for each of the two reactions. .arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone i. Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide. ii. Why doesn’t the cis isomer yield the oxide?. iii. Write the mechanism for each of the two reactions.arrow_forward
- When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone A.Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide B.Why doesn’t the cis isomer yield the oxide? C.Write the mechanism for each of the two reactions.arrow_forwardComplete this table for different amine compounds. Chemical propylamine quaternary ammonium ion methylphenylamine Molecular formula C3H9N C₂H7N C5H13N C4H10N Structural formula (CH3)3N (CH3)2NH CH 3 I (CH₂) 11 | H3C(CH2) 11 -N-(CH₂)11CH3 NHCH3 (CH₂)11 CH3 CH3CH2CH2-NH-CH3 + Classification Tertiary Quaternary Tertiary Secondaryarrow_forward
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