Textbook Question
Propanamide and methyl acetate have about the same molar mass, both are quite soluble in water, and yet the boiling point of propanamide is 213 °C, whereas that of methyl acetate is 57 °C. Explain.
Ch.17 Carboxylic Acids and Their Derivatives
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 17, Problem 74
Cyclic ribose nucleotide phosphates, such as cyclic AMP (cAMP), are important signaling agents in living cells; all have the general structure shown here. What kind of linkage holds the phosphate to the ribose (see arrows; ribose is highlighted in blue)?
Verified step by step guidance1
Identify the structure of the ribose sugar: Ribose is a five-carbon sugar with hydroxyl (-OH) groups attached to its carbon atoms. In this case, the ribose is cyclic, forming a furanose ring structure.
Examine the phosphate group: The phosphate group is attached to the ribose sugar through specific bonds. Look at the arrows in the image to determine which carbons of the ribose are involved in the linkage.
Determine the type of bond: The phosphate group forms ester linkages with the hydroxyl groups on the ribose. Specifically, these are phosphoester bonds, which occur when a phosphate group reacts with an -OH group, releasing water.
Analyze the cyclic nature: In cyclic AMP (cAMP), the phosphate group forms two ester linkages with two different hydroxyl groups on the ribose, creating a cyclic structure. This is known as a cyclic phosphodiester bond.
Conclude the linkage type: The linkage holding the phosphate to the ribose in cyclic AMP is a cyclic phosphodiester bond, as the phosphate is connected to two hydroxyl groups on the ribose, forming a ring structure.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cyclic Nucleotide Structure
Cyclic nucleotides, like cyclic AMP (cAMP), are formed by the cyclization of ribonucleotides. This structure includes a ribose sugar, a phosphate group, and a nitrogenous base. The cyclic nature arises from a covalent bond that connects the phosphate group to the ribose, creating a ring structure that is crucial for their function as signaling molecules.
Recommended video:
Guided course
1:19
Nucleoside and Nucleotide Formation Concept 2
Phosphate-Ribose Linkage
The linkage between the phosphate group and the ribose in cyclic nucleotides is a phosphoester bond. This bond forms when the hydroxyl group of the ribose sugar reacts with the phosphate group, resulting in the release of a water molecule. This covalent bond is essential for the stability and functionality of cyclic nucleotides in cellular signaling.
Recommended video:
Guided course
1:44Glycosidic Linkage Formation Concept 1
Signaling Role of cAMP
Cyclic AMP (cAMP) serves as a secondary messenger in various signaling pathways within cells. It is produced from ATP by the enzyme adenylate cyclase and activates protein kinase A (PKA), which then phosphorylates target proteins to elicit cellular responses. Understanding the role of cAMP is vital for grasping how cells communicate and respond to external stimuli.
Recommended video:
Guided course
03:25The Genetic Code Concept 1
Related Practice
Textbook Question
Mention at least two simple chemical tests by which you can distinguish between benzaldehyde and benzoic acid.
Textbook Question
What is the difference between a phosphate diester and an ester of a diphosphate? Give an example of each.
Textbook Question
In the following compound
a. Identify the phosphate ester linkage.
Textbook Question
In the following compound
b. Identify the phosphate anhydride linkage.
Textbook Question
A simple polyamide can be made from ethylenediamine and oxalic acid (Table 17.1). Draw the polymer formed when three units of ethylenediamine reacts with two units of oxalic acid.