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Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
All textbooksMcMurry 8th EditionCh.17 Carboxylic Acids and Their DerivativesProblem 71a
Chapter 17, Problem 71a

In the following compound
Chemical structure of a phosphate ester linkage with two phosphate groups connected to a benzyl group.
a. Identify the phosphate ester linkage.

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1
Examine the structure of the compound provided in the image. Look for a phosphate group, which is typically represented as a phosphorus atom (P) bonded to four oxygen atoms (O).
Identify the ester linkage within the phosphate group. An ester linkage is formed when a phosphate group is bonded to an organic group (such as a carbon chain) through an oxygen atom.
Locate the specific bond where the oxygen atom of the phosphate group is connected to a carbon atom of the organic molecule. This bond represents the phosphate ester linkage.
Verify that the identified linkage meets the criteria of a phosphate ester: a phosphorus atom bonded to an oxygen atom, which is further bonded to a carbon atom.
Highlight or label the phosphate ester linkage in the compound for clarity and confirmation of your identification.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Phosphate Ester Linkage

A phosphate ester linkage is a chemical bond formed between a phosphate group and an alcohol, resulting in the formation of an ester. In biological molecules, this linkage is crucial for the structure of nucleotides, which are the building blocks of nucleic acids like DNA and RNA. The phosphate group connects to the hydroxyl group of the sugar molecule, facilitating the formation of the backbone of nucleic acids.
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Nucleotide Structure

Nucleotides are the basic units of nucleic acids, consisting of three components: a nitrogenous base, a five-carbon sugar, and a phosphate group. The arrangement of these components determines the identity of the nucleotide and its role in genetic information storage and transfer. Understanding nucleotide structure is essential for identifying the phosphate ester linkages in nucleic acids.
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Chemical Bonding in Biochemistry

Chemical bonding in biochemistry refers to the interactions that hold molecules together, including covalent bonds, ionic bonds, and hydrogen bonds. In the context of nucleic acids, covalent bonds, such as the phosphate ester linkages, are particularly important as they provide stability and integrity to the molecular structure. Recognizing these bonds is key to understanding how biological molecules function and interact.
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Related Practice
Textbook Question

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)?

Textbook Question

What is the difference between a phosphate diester and an ester of a diphosphate? Give an example of each.

Textbook Question

Household soap is a mixture of the sodium or potassium salts of long-chain carboxylic acids that arise from saponification of animal fat.

b. Draw the structures of the soap molecules produced in the following reaction:

Textbook Question

In the following compound

b. Identify the phosphate anhydride linkage.

Textbook Question

When both the carboxylic acid and the amine are in the same molecule, amide formation produces lactams. A lactam is a cyclic amide, where the amide group is part of the ring. Draw the structure of the product(s) obtained from acid hydrolysis of these lactams.

a.

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.