Principles of General, Organic, Biological Chemistry
2nd Edition
ISBN: 9780073511191
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Videos
Textbook Question
Chapter 12, Problem 12.59AP
Explain why two four-carbon organic molecules have very different solubility properties: 1-butanol (CH3CH2CH2CH2OH) is water soluble but 1-chlorobutane CH3CH2CH2CH2Cl) is water insoluble.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Determining Intermolecular Forces in Organic Compounds
Rank the following compounds in order of increasing strength of intermolecular forces: CH3CH2CH2CH2CH3 (pentane), CH3CH2CH2CH2OH (butan-1-ol), and CH3CH2CH2CHO (butanal).
Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.
Which is NOT a physical property of alcohols or phenols?
O Phenols are generally only slightly soluble in water.
O The hydroxyl group of an alcohol is nonpolar.
The solubilities of normal primary alcohols in water
decrease with increasing molecular weight.
Boiling points of normal primary alcohols increase
with increasing molecular weight.
Chapter 12 Solutions
Principles of General, Organic, Biological Chemistry
Ch. 12.1 - a. Label the hydroxyl groups, thiols, halogens,...Ch. 12.1 - Draw out each compound to clearly show what groups...Ch. 12.2 - Classify each alcohol as 1, 2, or 3.Ch. 12.2 - Classify each hydroxyl group in sorbitol as 1, 2,...Ch. 12.2 - Which compound in each pair has the higher boiling...Ch. 12.2 - Label each compound as water soluble or water...Ch. 12.2 - Give the IUPAC name for each compound.Ch. 12.2 - Give the structure corresponding to each name. a....Ch. 12.3 - Name each ether. a. CH3OCH2CH2CH2CH3 b....Ch. 12.3 - Prob. 12.10P
Ch. 12.3 - Which compound in each pair has the higher boiling...Ch. 12.5 - Prob. 12.12PCh. 12.5 - Prob. 12.13PCh. 12.6 - Prob. 12.14PCh. 12.6 - Prob. 12.15PCh. 12.6 - Give the structure corresponding to each name. a....Ch. 12.7 - Prob. 12.17PCh. 12.8 - Give the IUPAC name for each aldehyde. a....Ch. 12.8 - Prob. 12.19PCh. 12.8 - Give the IUPAC name for each aldehyde depicted in...Ch. 12.8 - Prob. 12.21PCh. 12.8 - Prob. 12.22PCh. 12.8 - Acetone and progesterone are two ketones that...Ch. 12.9 - Prob. 12.24PCh. 12.10 - Prob. 12.25PCh. 12.11 - Prob. 12.26PCh. 12.11 - Prob. 12.27PCh. 12.11 - Prob. 12.28PCh. 12.11 - Prob. 12.29PCh. 12.11 - Prob. 12.30PCh. 12.11 - Prob. 12.31PCh. 12.11 - Prob. 12.32PCh. 12 - Prob. 12.33UKCCh. 12 - Prob. 12.34UKCCh. 12 - Consider the following ball-and-stick model of an...Ch. 12 - Consider the following ball-and-stick model. a....Ch. 12 - Name each compound. a. CH3CH2OCH2CH2CH2CH3Ch. 12 - Name each compound. a. CH3OCH2CH2CH3 b....Ch. 12 - Answer the following questions about alcohol A. a....Ch. 12 - Answer the following questions about alcohol B. a....Ch. 12 - Prob. 12.41UKCCh. 12 - Prob. 12.42UKCCh. 12 - Prob. 12.43UKCCh. 12 - Prob. 12.44UKCCh. 12 - Prob. 12.45APCh. 12 - Prob. 12.46APCh. 12 - Prob. 12.47APCh. 12 - Prob. 12.48APCh. 12 - Prob. 12.49APCh. 12 - Prob. 12.50APCh. 12 - Prob. 12.51APCh. 12 - Prob. 12.52APCh. 12 - Prob. 12.53APCh. 12 - Give the structure corresponding to each name. a....Ch. 12 - Prob. 12.55APCh. 12 - Draw structures for the four constitutional...Ch. 12 - Prob. 12.57APCh. 12 - Rank the following compounds in order of...Ch. 12 - Explain why two four-carbon organic molecules have...Ch. 12 - Explain why the boiling point of CH3CH2CH2CH2OH...Ch. 12 - Which compound in each pair has the higher boiling...Ch. 12 - Which compound in each pair is more water soluble?...Ch. 12 - Prob. 12.63APCh. 12 - Prob. 12.64APCh. 12 - Prob. 12.65APCh. 12 - Prob. 12.66APCh. 12 - Prob. 12.67APCh. 12 - Xylitol is a nontoxic compound as sweet as table...Ch. 12 - Prob. 12.69APCh. 12 - Prob. 12.70APCh. 12 - Prob. 12.71APCh. 12 - Prob. 12.72APCh. 12 - Prob. 12.73APCh. 12 - Prob. 12.74APCh. 12 - Prob. 12.75APCh. 12 - Prob. 12.76APCh. 12 - Prob. 12.77APCh. 12 - Draw the structure corresponding to each name. a....Ch. 12 - Prob. 12.79APCh. 12 - Prob. 12.80APCh. 12 - What product is formed when each compound is...Ch. 12 - Prob. 12.82APCh. 12 - Prob. 12.83APCh. 12 - Prob. 12.84APCh. 12 - Prob. 12.85APCh. 12 - Prob. 12.86APCh. 12 - Prob. 12.87APCh. 12 - Label each of the following objects as chiral or...Ch. 12 - Prob. 12.89APCh. 12 - Prob. 12.90APCh. 12 - Prob. 12.91APCh. 12 - Prob. 12.92APCh. 12 - Prob. 12.93APCh. 12 - Prob. 12.94APCh. 12 - Prob. 12.95APCh. 12 - Prob. 12.96APCh. 12 - Prob. 12.97APCh. 12 - How are the compounds in each pair related? Are...Ch. 12 - Prob. 12.99APCh. 12 - Prob. 12.100APCh. 12 - Prob. 12.101APCh. 12 - Prob. 12.102APCh. 12 - Prob. 12.103APCh. 12 - Lactic acid [CH3CH(OH)CO2H] gives sour milk its...Ch. 12 - Prob. 12.105APCh. 12 - Prob. 12.106APCh. 12 - Prob. 12.107CPCh. 12 - Prob. 12.108CPCh. 12 - Prob. 12.109BTCCh. 12 - Prob. 12.110BTC
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider four compounds that have nearly the same molecular weights: 1,2-dimethoxyethane, ethyl propyl ether, hexane, and 1-pentanol. Which would you expect to have the highest boilingpoint? Which would be most soluble in water? Explain the reasons for your choices.arrow_forwardWhat is the intermolecular force between carbon tetrachloride and water. What about carbon tetrachloride and cyclohexane? Is carbon tetrachloride more soluble in water or cyclohexane?arrow_forwardGive the IUPAC name or common name of the isomer of 1-hexanol that has the highest vapor pressure.arrow_forward
- The molecular mass of 1-butanol, C4H9OH, is 74.12 amu; that of ethylene glycol, CH2(OH)CH2OH, is 62.07 amu, yet their boiling points are 117.7°C and 197.3°C, respectively. Explain the reason for the difference. Since ethylene glycol h --Select-- locations for hydrogen bonding interactions than 1-butanol, it will have the higher boiling point. more fewerarrow_forwardFor phenol and ether, explain the solubility behavior in water as a function of the relative proportions of hydrophilic bonds and hydrophobic bonds.arrow_forwardWhich of the following would be LEAST soluble in water? CH3CH₂CH₂CH₂OH CH3CH₂CH₂OH All of these would have about the same solubility in water. heptane O CH3CH₂CH₂CH₂CH₂NH₂arrow_forward
- Which is most soluble in water? Explain. Draw a molecule showing how it interacts with water molecules. cis-2-pentene 1-butanol butanonearrow_forwardExplain why these compounds (1-propanol, ethylene glycol, and ethanethiol) experience different intermolecular forces based on their molecular structure.arrow_forwardWhy are the boiling points of ethers similar to those of alkanes instead of alcohols? a) Both ether molecules and alkane molecules are polar, whereas alcohol molecules are nonpolar. b) Hydrogen bonding between ether molecules is strong and this property is similar to that of alkanes. However, hydrogen bonding is weaker in alcohols than it is in both ethers and alkanes. c) Although ether molecules are polar, they cannot form hydrogen bonds with other ether molecules. Similarly, alkane molecules do not form hydrogen bonds, whereas there is hydrogen bonding in alcohols. d) None of these are correct explanations.arrow_forward
- Why is 1-butanol, CH₃CH₂CH₂CH-OH, soluble in water, while heptane, CH₃(CH₂)₅CH₃, is not?arrow_forwardDifferentiate petroleum ether and sulfuric ether in terms of solubility in waterarrow_forwardDraw diagrams showing how isopropyl alcohol, ethylene glycol and glycerol can hydrogen bond to themselves. Draw the structure of ethanol, 1-hexanol, cyclohexanol, glycerol, benzyl alcohol, phenol and salicylic acid. Draw the resonance structure of phenoxide ion.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
Introductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Introductory Chemistry: An Active Learning Approa...
Chemistry
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Cengage Learning
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY