Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 17, Problem 17.16P
Interpretation Introduction
Interpretation:
The boiling point of acetic acid is higher than that of its methyl ester even through acetic acid has a lower molecular weight. The factors behind this has to be given.
Concept introduction:
The boiling points of carboxylic acids are higher than those of alcohol or
Intermolecular hydrogen bonding will increase the boiling point of an organic compound.
Carboxylic acids can form dimers in which hydrogen bonds form between two carboxyl groups this will also increase their boiling point.
Increasing order of boiling point of some organic compounds with similar molecular weight is shown below,
The better hydrogen bond capability of a molecule will increase its boiling points.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Acetic acid has a boiling point of 118°C, whereas its methyl ester has a boiling point of 57°C. Account for the fact that the boiling point of acetic acid is higher than that of its methyl ester even though acetic acid has a lower molecular weight.
With reference to the structures of acetylsalicylic acid (aspirin) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin tablets slowly decompose over time.
Which of the following statements is INCORRECT concerning the two acids below?
Options:
Acetic acid has higher water solubility than benzoic acid.
Acetic acid has a higher melting point than benzoic acid.
Benzoic acid has a larger conjugated system.
Benzoic acid is the stronger acid.
Acetic acid has an electron donating group in it's structure.
Chapter 17 Solutions
Organic Chemistry
Ch. 17.2 - Prob. 17.1PCh. 17.4 - Which is the stronger acid in each pair?Ch. 17.4 - Prob. 17.3PCh. 17.7 - Prob. 17.4PCh. 17.8 - Prob. 17.5PCh. 17.8 - Prob. AQCh. 17.8 - Prob. BQCh. 17.8 - Prob. CQCh. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.9 - Prob. 17.6P
Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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
- Identify the most important aldehyde and ketone from Section 14.4 on the basis of amount used, and list at least one characteristic for each that contributes to its usefulness.arrow_forwardGive the products formed when Benzaldehyde and Benzoic Acid are treated with the given reagents. a. Tollen’s reagentb. phenylhydrazine, H+c. HCNarrow_forwardWhich of the following materials will most likely form an ester too if subjected to the same process as aspirin synthesis? A Benzoic Acid B Benzamide C Benzaldehyde D Benzenolarrow_forward
- What products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiflu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating influenza. Aspartame [part (b)] is the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forwardwhy n-hexanol has higher boiling point than n-hexane. why acetic acid is more acidic then butanoic acid. why sugar is soluble in water in terms of their molecular interactions.arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Part A Given 7.30 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. Part B A chemist ran the reaction and obtained 5.95 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. Part C The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 7.30 gg of…arrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.45 gg of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%% yield? Express your answer in grams to three significant figures. A chemist ran the reaction and obtained 5.50 gg of ethyl butyrate. What was the percent yield? Express your answer as a percent to three significant figures. The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0%% yield. How many grams would be produced from 8.45 gg of butanoic acid and excess…arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring. It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)CH3CH2CH2CO2H(l)+CH2CH3OH(l)⟶H+CH3CH2CH2CO2CH2CH3(l)+H2O(l) A chemist ran the reaction and obtained 5.40 g of ethyl butyrate. What was the percent yield, The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.45g of butanoic acid and excess ethanol?arrow_forwardWhy does a substance become more soluble in a solvent with increasing temperature? Solvents are ordered by decreasing value of theirdielectric constant. In the table, which is the most polar solvent and which is the least polar? How can acetylsalicylic acid be obtained from salicylic acid?arrow_forward
- Which is more polar? Ketone Vs Aryl Chloride Ether vs Aryl Chloride Amine vs ARyl Chloridearrow_forwardWhich of the following compounds will NOT test positive in a hydroxamic test? a. butanoic acid b. butanoyl chloride c. butyl ethanoate d. butanoic acid anhydridearrow_forwardWhat products are formed when all of the amide and ester bonds are hydrolyzed in each of the following compounds? Tamiu [part (a)] is the trade name of the antiviral agent oseltamivir, thought to be the most effective agent in treating inuenza. Aspartame [part (b)] is the articial sweetener used in Equal and many diet beverages. One of the products ofthis hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identied early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher: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
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning