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Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 17, Problem 49

Fumaric acid is a metabolic intermediate that has the systematic name trans-2-butenedioic acid. Draw its structure.

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1
Understand the systematic name 'trans-2-butenedioic acid': The 'trans' prefix indicates that the molecule has a trans configuration, meaning the substituents on the double bond are on opposite sides. The '2-butenedioic acid' part indicates a four-carbon chain with a double bond between carbons 2 and 3, and two carboxylic acid (-COOH) groups, one on each end of the chain.
Start by drawing the carbon backbone: Draw a chain of four carbon atoms in a straight line. Label the carbons as C1, C2, C3, and C4.
Add the double bond: Place a double bond between C2 and C3 to represent the 'butene' part of the name.
Attach the carboxylic acid groups: Add a -COOH group to C1 and another -COOH group to C4. These groups represent the 'dioic acid' part of the name.
Ensure the trans configuration: Arrange the substituents on the double-bonded carbons (C2 and C3) so that the -COOH group on C2 is opposite to the hydrogen atom on C3, and vice versa. This ensures the trans configuration is correctly represented.

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Key Concepts

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

Metabolic Intermediates

Metabolic intermediates are compounds that form during the metabolic pathways of organisms. They play crucial roles in various biochemical processes, acting as substrates or products in enzymatic reactions. Understanding these intermediates is essential for grasping how energy and materials are transformed within cells.
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Chemical Structure

The chemical structure of a compound refers to the arrangement of atoms within the molecule, including the types of bonds and the spatial orientation of the atoms. For fumaric acid, recognizing its structure as a dicarboxylic acid with a specific geometric configuration (trans) is vital for understanding its chemical properties and reactivity.
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Systematic Naming in Chemistry

Systematic naming in chemistry, governed by IUPAC rules, provides a standardized way to name chemical compounds based on their structure and functional groups. Fumaric acid's systematic name, trans-2-butenedioic acid, indicates its specific configuration and functional groups, which is important for identifying and communicating about the compound in scientific contexts.
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